[PM-21034] Feature Branch - "User Crypto V2" (#5982)

* [PM-21034] Database changes for signature keypairs (#5906)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Drop view if exists

* Enable nullable

* Replace with create or alter view

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* [PM-21034] Implement api changes to retreive signing keys (#5932)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Add initial get keys endpoint

* Add sync response

* Cleanup

* Add query and fix types

* Add tests and cleanup

* Fix test

* Drop view if exists

* Add km queries

* Cleanup

* Enable nullable

* Cleanup

* Cleanup

* Enable nullable

* Fix incorrect namespace

* Remove unused using

* Fix test build

* Fix build error

* Fix build

* Attempt to fix tests

* Attempt to fix tests

* Replace with create or alter view

* Attempt to fix tests

* Attempt to fix build

* Rename to include async suffix

* Fix test

* Rename repo

* Attempt to fix tests

* Cleanup

* Test

* Undo test

* Fix tests

* Fix test

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Fix build

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Cleanup and move query to core

* Fix test

* Fix build

* Fix tests

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Switch away from primary constructor

* Use argumentNullException

* Add test

* Pass user account keys directly to profileresponsemodel

* Move registration to core

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove empty line

* Apply suggestions

* Fix tests

* Fix tests

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* [PM-22384] Implement key-rotation based enrollment to user-crypto v2 (#5934)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Add initial get keys endpoint

* Add sync response

* Cleanup

* Add query and fix types

* Add tests and cleanup

* Fix test

* Drop view if exists

* Add km queries

* Cleanup

* Enable nullable

* Cleanup

* Cleanup

* Enable nullable

* Fix incorrect namespace

* Remove unused using

* Fix test build

* Fix build error

* Fix build

* Attempt to fix tests

* Attempt to fix tests

* Replace with create or alter view

* Attempt to fix tests

* Attempt to fix build

* Rename to include async suffix

* Fix test

* Rename repo

* Attempt to fix tests

* Cleanup

* Test

* Undo test

* Fix tests

* Fix test

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Fix build

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Cleanup

* Add migration to user encryption v2

* Fix build

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Cleanup

* Cleanup

* Fix build

* Fix test

* Add validation

* Fix test

* Apply fixes

* Fix tests

* Improve tests

* Add tests

* Add error message validation

* Fix tests

* Fix tests

* Fix test

* Add test

* Fix tests and errors

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Cleanup and move query to core

* Fix test

* Fix build

* Fix tests

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Switch away from primary constructor

* Use argumentNullException

* Add test

* Pass user account keys directly to profileresponsemodel

* Fix build

* Fix namespace

* Make signedpublickey optional

* Remove unused file

* Fix cases for request data conversion

* Revert constructor change

* Undo comments change

* Apply fixes

* Move registration to core

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove empty line

* Apply suggestions

* Fix tests

* Fix tests

* Fix build of integration tests

* Attempt to fix tests

* Add test

* Move v2 encryption user async below public functions

* Add todo

* Rename to have async suffix

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Address feedback

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test coverage

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Split up validation from rotation

* Fix tests

* Increase test coverage

* Rename tests

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test for no signature keypair data

* Fix build

* Enable nullable

* Fix build

* Clean up data model

* Fix tests

* Cleanup

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>
Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Fix build

* [PM-22862] Account security version (#5995)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Add initial get keys endpoint

* Add sync response

* Cleanup

* Add query and fix types

* Add tests and cleanup

* Fix test

* Drop view if exists

* Add km queries

* Cleanup

* Enable nullable

* Cleanup

* Cleanup

* Enable nullable

* Fix incorrect namespace

* Remove unused using

* Fix test build

* Fix build error

* Fix build

* Attempt to fix tests

* Attempt to fix tests

* Replace with create or alter view

* Attempt to fix tests

* Attempt to fix build

* Rename to include async suffix

* Fix test

* Rename repo

* Attempt to fix tests

* Cleanup

* Test

* Undo test

* Fix tests

* Fix test

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Fix build

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Cleanup

* Add migration to user encryption v2

* Fix build

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Cleanup

* Cleanup

* Fix build

* Fix test

* Add validation

* Fix test

* Apply fixes

* Fix tests

* Improve tests

* Add tests

* Add error message validation

* Fix tests

* Fix tests

* Fix test

* Add test

* Fix tests and errors

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Cleanup and move query to core

* Fix test

* Fix build

* Fix tests

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Switch away from primary constructor

* Use argumentNullException

* Add test

* Pass user account keys directly to profileresponsemodel

* Fix build

* Fix namespace

* Make signedpublickey optional

* Remove unused file

* Fix cases for request data conversion

* Revert constructor change

* Undo comments change

* Apply fixes

* Move registration to core

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove empty line

* Apply suggestions

* Fix tests

* Fix tests

* Fix build of integration tests

* Attempt to fix tests

* Add test

* Move v2 encryption user async below public functions

* Add todo

* Rename to have async suffix

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Address feedback

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test coverage

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Split up validation from rotation

* Fix tests

* Increase test coverage

* Rename tests

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test for no signature keypair data

* Fix build

* Enable nullable

* Fix build

* Clean up data model

* Fix tests

* Merge branch 'km/signing-upgrade-rotation' into km/account-security-version

* Add security state to rotation

* Update tests

* Update tests and check for security state in v2 model

* Cleanup

* Add tests

* Add security state data to integration test

* Re-sort and remove limit

* Update migrations

* Fix sql

* Fix sql

* Fix sql

* Fix fixture

* Fix test

* Fix test

* Fix test

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>
Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* [PM-22853] Add feature flag (#6090)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Add initial get keys endpoint

* Add sync response

* Cleanup

* Add query and fix types

* Add tests and cleanup

* Fix test

* Drop view if exists

* Add km queries

* Cleanup

* Enable nullable

* Cleanup

* Cleanup

* Enable nullable

* Fix incorrect namespace

* Remove unused using

* Fix test build

* Fix build error

* Fix build

* Attempt to fix tests

* Attempt to fix tests

* Replace with create or alter view

* Attempt to fix tests

* Attempt to fix build

* Rename to include async suffix

* Fix test

* Rename repo

* Attempt to fix tests

* Cleanup

* Test

* Undo test

* Fix tests

* Fix test

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Fix build

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Cleanup

* Add migration to user encryption v2

* Fix build

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Cleanup

* Cleanup

* Fix build

* Fix test

* Add validation

* Fix test

* Apply fixes

* Fix tests

* Improve tests

* Add tests

* Add error message validation

* Fix tests

* Fix tests

* Fix test

* Add test

* Fix tests and errors

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Cleanup and move query to core

* Fix test

* Fix build

* Fix tests

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Switch away from primary constructor

* Use argumentNullException

* Add test

* Pass user account keys directly to profileresponsemodel

* Fix build

* Fix namespace

* Make signedpublickey optional

* Remove unused file

* Fix cases for request data conversion

* Revert constructor change

* Undo comments change

* Apply fixes

* Move registration to core

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove empty line

* Apply suggestions

* Fix tests

* Fix tests

* Fix build of integration tests

* Attempt to fix tests

* Add test

* Move v2 encryption user async below public functions

* Add todo

* Rename to have async suffix

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Address feedback

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test coverage

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Split up validation from rotation

* Fix tests

* Increase test coverage

* Rename tests

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test for no signature keypair data

* Fix build

* Enable nullable

* Fix build

* Clean up data model

* Fix tests

* Merge branch 'km/signing-upgrade-rotation' into km/account-security-version

* Add security state to rotation

* Update tests

* Add feature flag

* Update tests and check for security state in v2 model

* Cleanup

* Add tests

* Add security state data to integration test

* Re-sort and remove limit

* Update migrations

* Fix sql

* Fix sql

* Fix sql

* Fix fixture

* Fix test

* Fix test

* Fix test

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>
Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* [PM-23222] Update revision date on key rotation (#6038)

* Add signing key repositories, models, and sql migration scripts

* Rename UserSigningKeys table to UserSigningKey

* Rename signedpublickeyownershipclaim to signedpublickey

* Move signedPublicKey to last parameter

* Add newline at end of file

* Rename to signature key pair

* Further rename to signaturekeypair

* Rename to UserSignatureKeyPairRepository

* Add newline

* Rename more instances to UserSignatureKeyPair

* Update parameter order

* Fix order

* Add more renames

* Cleanup

* Fix sql

* Add ef migrations

* Fix difference in SQL SP compared to migration SP

* Fix difference in SQL SP vs migration

* Fix difference in SQL SP vs migration

* Attempt to fix sql

* Rename migration to start later

* Address feedback

* Move UserSignatureKeyPair to KM codeownership

* Fix build

* Fix build

* Fix build

* Move out entitytypeconfiguration

* Use view for reading usersignaturekeypairs

* Fix migration script

* Fix migration script

* Add initial get keys endpoint

* Add sync response

* Cleanup

* Add query and fix types

* Add tests and cleanup

* Fix test

* Drop view if exists

* Add km queries

* Cleanup

* Enable nullable

* Cleanup

* Cleanup

* Enable nullable

* Fix incorrect namespace

* Remove unused using

* Fix test build

* Fix build error

* Fix build

* Attempt to fix tests

* Attempt to fix tests

* Replace with create or alter view

* Attempt to fix tests

* Attempt to fix build

* Rename to include async suffix

* Fix test

* Rename repo

* Attempt to fix tests

* Cleanup

* Test

* Undo test

* Fix tests

* Fix test

* Switch go generatecomb

* Switch to generatecomb

* Move signature algorithm

* Move useresignaturekeypairentitytypeconfiguration to km ownership

* Move userSignatureKeyPair model

* Unswap file names

* Move sql files to km ownership

* Add index on userid for signature keys

* Fix wrong filename

* Fix build

* Remove string length limit

* Regenerate EF migrations

* Undo changes to program.cs

* Cleanup

* Add migration to user encryption v2

* Fix build

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update util/Migrator/DbScripts/2025-06-01_00_AddSignatureKeyPairTable.sql

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Rename dbset to plural

* Cleanup

* Cleanup

* Fix build

* Fix test

* Add validation

* Fix test

* Apply fixes

* Fix tests

* Improve tests

* Add tests

* Add error message validation

* Fix tests

* Fix tests

* Fix test

* Add test

* Fix tests and errors

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Cleanup and move query to core

* Fix test

* Fix build

* Fix tests

* Update src/Api/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Switch away from primary constructor

* Use argumentNullException

* Add test

* Pass user account keys directly to profileresponsemodel

* Fix build

* Fix namespace

* Make signedpublickey optional

* Remove unused file

* Fix cases for request data conversion

* Revert constructor change

* Undo comments change

* Apply fixes

* Move registration to core

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/Startup.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove empty line

* Apply suggestions

* Fix tests

* Fix tests

* Fix build of integration tests

* Attempt to fix tests

* Add test

* Move v2 encryption user async below public functions

* Add todo

* Rename to have async suffix

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Address feedback

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test coverage

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Split up validation from rotation

* Fix tests

* Increase test coverage

* Rename tests

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Update src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Add test for no signature keypair data

* Fix build

* Enable nullable

* Fix build

* Clean up data model

* Fix tests

* Merge branch 'km/signing-upgrade-rotation' into km/account-security-version

* Add security state to rotation

* Update tests

* Update revision date on key rotation

* Update tests and check for security state in v2 model

* Cleanup

* Add tests

* Add security state data to integration test

* Re-sort and remove limit

* Update migrations

* Fix sql

* Fix sql

* Fix sql

* Fix fixture

* Fix test

* Fix test

* Fix test

* Add test for change date

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>
Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

* Fix signing keys

* Update sql migrations

* Fix tests

* Add keys to identity token response

* Fix tests

* Fix tests

* Fix formatting

* Update src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Infrastructure.Dapper/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Controllers/UsersController.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Requests/SignatureKeyPairRequestModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Api/KeyManagement/Models/Requests/PublicKeyEncryptionKeyPairRequestModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Entities/UserSignatureKeyPair.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Repositories/IUserSignatureKeyPairRepository.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Queries/UserAccountKeysQuery.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Data/PublicKeyEncryptionKeyPairData.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Entities/UserSignatureKeyPair.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Data/RotateUserAccountKeysData.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Data/SignatureKeyPairData.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Data/SecurityStateData.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Data/UserAccountKeysData.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Request/SecurityStateModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Response/PrivateKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Response/PublicKeysResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Response/PublicKeyEncryptionKeyPairResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Queries/Interfaces/IUserAcountKeysQuery.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Update src/Core/KeyManagement/Models/Response/SignatureKeyPairResponseModel.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Remove unnecessary file

* Add eof spacing

* Move models

* Fix build

* Move models to API subdirectory

* Rename model

* Remove migrations

* Add new ef migrations

* Remove empty line

* Only query account keys if the user has keys

* Dotnet format

* Fix test

* Update test/Identity.Test/IdentityServer/BaseRequestValidatorTests.cs

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>

* Apply suggestion

* Fix whitespace

* Force camel case on response models

* Address feedback for sql files

* Fix build

* Make index unique

* Add contstraints

* Fix sql

* Fix order

* Cleanup

* Fix build

* Update migrations

* Update EF migrations

* Change parameters to nvarchar

* Update to Varchar

* Apply feedback

* Move refresh view

* Attempt to fix build

* Undo sql changes

* Apply feedback about varchar

* Apply feedback about refresh view

* Apply feedback about new lines

* Address SQL feedback

* Re-sort columns

* Fix build

* Fix order

* Fix build

---------

Co-authored-by: Thomas Avery <43214426+Thomas-Avery@users.noreply.github.com>
Co-authored-by: Maciej Zieniuk <167752252+mzieniukbw@users.noreply.github.com>

src/Api/Auth/Controllers/AccountsController.cs

@@ -18,6 +18,7 @@ using Bit.Core.Auth.UserFeatures.UserMasterPassword.Interfaces;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.KeyManagement.Kdf;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Api.Response;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -40,6 +41,7 @@ public class AccountsController : Controller
     private readonly ITdeOffboardingPasswordCommand _tdeOffboardingPasswordCommand;
     private readonly ITwoFactorIsEnabledQuery _twoFactorIsEnabledQuery;
     private readonly IFeatureService _featureService;
+    private readonly IUserAccountKeysQuery _userAccountKeysQuery;
     private readonly ITwoFactorEmailService _twoFactorEmailService;
     private readonly IChangeKdfCommand _changeKdfCommand;
 
@@ -53,6 +55,7 @@ public class AccountsController : Controller
         ITdeOffboardingPasswordCommand tdeOffboardingPasswordCommand,
         ITwoFactorIsEnabledQuery twoFactorIsEnabledQuery,
         IFeatureService featureService,
+        IUserAccountKeysQuery userAccountKeysQuery,
         ITwoFactorEmailService twoFactorEmailService,
         IChangeKdfCommand changeKdfCommand
         )
@@ -66,6 +69,7 @@ public class AccountsController : Controller
         _tdeOffboardingPasswordCommand = tdeOffboardingPasswordCommand;
         _twoFactorIsEnabledQuery = twoFactorIsEnabledQuery;
         _featureService = featureService;
+        _userAccountKeysQuery = userAccountKeysQuery;
         _twoFactorEmailService = twoFactorEmailService;
         _changeKdfCommand = changeKdfCommand;
     }
@@ -332,7 +336,9 @@ public class AccountsController : Controller
         var hasPremiumFromOrg = await _userService.HasPremiumFromOrganization(user);
         var organizationIdsClaimingActiveUser = await GetOrganizationIdsClaimingUserAsync(user.Id);
 
-        var response = new ProfileResponseModel(user, organizationUserDetails, providerUserDetails,
+        var accountKeys = await _userAccountKeysQuery.Run(user);
+
+        var response = new ProfileResponseModel(user, accountKeys, organizationUserDetails, providerUserDetails,
             providerUserOrganizationDetails, twoFactorEnabled,
             hasPremiumFromOrg, organizationIdsClaimingActiveUser);
         return response;
@@ -364,8 +370,9 @@ public class AccountsController : Controller
         var twoFactorEnabled = await _twoFactorIsEnabledQuery.TwoFactorIsEnabledAsync(user);
         var hasPremiumFromOrg = await _userService.HasPremiumFromOrganization(user);
         var organizationIdsClaimingActiveUser = await GetOrganizationIdsClaimingUserAsync(user.Id);
+        var userAccountKeys = await _userAccountKeysQuery.Run(user);
 
-        var response = new ProfileResponseModel(user, null, null, null, twoFactorEnabled, hasPremiumFromOrg, organizationIdsClaimingActiveUser);
+        var response = new ProfileResponseModel(user, userAccountKeys, null, null, null, twoFactorEnabled, hasPremiumFromOrg, organizationIdsClaimingActiveUser);
         return response;
     }
 
@@ -389,8 +396,9 @@ public class AccountsController : Controller
         var userTwoFactorEnabled = await _twoFactorIsEnabledQuery.TwoFactorIsEnabledAsync(user);
         var userHasPremiumFromOrganization = await _userService.HasPremiumFromOrganization(user);
         var organizationIdsClaimingActiveUser = await GetOrganizationIdsClaimingUserAsync(user.Id);
+        var accountKeys = await _userAccountKeysQuery.Run(user);
 
-        var response = new ProfileResponseModel(user, null, null, null, userTwoFactorEnabled, userHasPremiumFromOrganization, organizationIdsClaimingActiveUser);
+        var response = new ProfileResponseModel(user, accountKeys, null, null, null, userTwoFactorEnabled, userHasPremiumFromOrganization, organizationIdsClaimingActiveUser);
         return response;
     }
 

src/Api/Billing/Controllers/AccountsController.cs

@@ -1,4 +1,5 @@
 #nullable enable
+
 using Bit.Api.Models.Request;
 using Bit.Api.Models.Request.Accounts;
 using Bit.Api.Models.Response;
@@ -8,6 +9,7 @@ using Bit.Core.Billing.Models;
 using Bit.Core.Billing.Models.Business;
 using Bit.Core.Billing.Services;
 using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Business;
 using Bit.Core.Services;
 using Bit.Core.Settings;
@@ -21,7 +23,8 @@ namespace Bit.Api.Billing.Controllers;
 [Authorize("Application")]
 public class AccountsController(
     IUserService userService,
-    ITwoFactorIsEnabledQuery twoFactorIsEnabledQuery) : Controller
+    ITwoFactorIsEnabledQuery twoFactorIsEnabledQuery,
+    IUserAccountKeysQuery userAccountKeysQuery) : Controller
 {
     [HttpPost("premium")]
     public async Task<PaymentResponseModel> PostPremiumAsync(
@@ -58,8 +61,9 @@ public class AccountsController(
         var userTwoFactorEnabled = await twoFactorIsEnabledQuery.TwoFactorIsEnabledAsync(user);
         var userHasPremiumFromOrganization = await userService.HasPremiumFromOrganization(user);
         var organizationIdsClaimingActiveUser = await GetOrganizationIdsClaimingUserAsync(user.Id);
+        var accountKeys = await userAccountKeysQuery.Run(user);
 
-        var profile = new ProfileResponseModel(user, null, null, null, userTwoFactorEnabled,
+        var profile = new ProfileResponseModel(user, accountKeys, null, null, null, userTwoFactorEnabled,
             userHasPremiumFromOrganization, organizationIdsClaimingActiveUser);
         return new PaymentResponseModel
         {

src/Api/Controllers/UsersController.cs

@@ -1,33 +0,0 @@
-using Bit.Api.Models.Response;
-using Bit.Core.Exceptions;
-using Bit.Core.Repositories;
-using Microsoft.AspNetCore.Authorization;
-using Microsoft.AspNetCore.Mvc;
-
-namespace Bit.Api.Controllers;
-
-[Route("users")]
-[Authorize("Application")]
-public class UsersController : Controller
-{
-    private readonly IUserRepository _userRepository;
-
-    public UsersController(
-        IUserRepository userRepository)
-    {
-        _userRepository = userRepository;
-    }
-
-    [HttpGet("{id}/public-key")]
-    public async Task<UserKeyResponseModel> Get(string id)
-    {
-        var guidId = new Guid(id);
-        var key = await _userRepository.GetPublicKeyAsync(guidId);
-        if (key == null)
-        {
-            throw new NotFoundException();
-        }
-
-        return new UserKeyResponseModel(guidId, key);
-    }
-}

src/Api/KeyManagement/Controllers/AccountsKeyManagementController.cs

@@ -106,8 +106,7 @@ public class AccountsKeyManagementController : Controller
         {
             OldMasterKeyAuthenticationHash = model.OldMasterKeyAuthenticationHash,
 
-            UserKeyEncryptedAccountPrivateKey = model.AccountKeys.UserKeyEncryptedAccountPrivateKey,
+            AccountKeys = model.AccountKeys.ToAccountKeysData(),
-            AccountPublicKey = model.AccountKeys.AccountPublicKey,
 
             MasterPasswordUnlockData = model.AccountUnlockData.MasterPasswordUnlockData.ToUnlockData(),
             EmergencyAccesses = await _emergencyAccessValidator.ValidateAsync(user, model.AccountUnlockData.EmergencyAccessUnlockData),

src/Api/KeyManagement/Controllers/UsersController.cs

@@ -0,0 +1,39 @@
+using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Models.Api.Response;
+using Bit.Core.KeyManagement.Queries.Interfaces;
+using Bit.Core.Repositories;
+using Microsoft.AspNetCore.Authorization;
+using Microsoft.AspNetCore.Mvc;
+using UserKeyResponseModel = Bit.Api.Models.Response.UserKeyResponseModel;
+
+
+namespace Bit.Api.KeyManagement.Controllers;
+
+[Route("users")]
+[Authorize("Application")]
+public class UsersController : Controller
+{
+    private readonly IUserRepository _userRepository;
+    private readonly IUserAccountKeysQuery _userAccountKeysQuery;
+
+    public UsersController(IUserRepository userRepository, IUserAccountKeysQuery userAccountKeysQuery)
+    {
+        _userRepository = userRepository;
+        _userAccountKeysQuery = userAccountKeysQuery;
+    }
+
+    [HttpGet("{id}/public-key")]
+    public async Task<UserKeyResponseModel> GetPublicKeyAsync([FromRoute] Guid id)
+    {
+        var key = await _userRepository.GetPublicKeyAsync(id) ?? throw new NotFoundException();
+        return new UserKeyResponseModel(id, key);
+    }
+
+    [HttpGet("{id}/keys")]
+    public async Task<PublicKeysResponseModel> GetAccountKeysAsync([FromRoute] Guid id)
+    {
+        var user = await _userRepository.GetByIdAsync(id) ?? throw new NotFoundException();
+        var accountKeys = await _userAccountKeysQuery.Run(user) ?? throw new NotFoundException("User account keys not found.");
+        return new PublicKeysResponseModel(accountKeys);
+    }
+}

src/Api/KeyManagement/Models/Requests/AccountKeysRequestModel.cs

@@ -1,4 +1,5 @@
-#nullable enable
+using Bit.Core.KeyManagement.Models.Api.Request;
+using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.Utilities;
 
 namespace Bit.Api.KeyManagement.Models.Requests;
@@ -7,4 +8,44 @@ public class AccountKeysRequestModel
 {
     [EncryptedString] public required string UserKeyEncryptedAccountPrivateKey { get; set; }
     public required string AccountPublicKey { get; set; }
+
+    public PublicKeyEncryptionKeyPairRequestModel? PublicKeyEncryptionKeyPair { get; set; }
+    public SignatureKeyPairRequestModel? SignatureKeyPair { get; set; }
+    public SecurityStateModel? SecurityState { get; set; }
+
+    public UserAccountKeysData ToAccountKeysData()
+    {
+        // This will be cleaned up, after a compatibility period, at which point PublicKeyEncryptionKeyPair and SignatureKeyPair will be required.
+        // TODO: https://bitwarden.atlassian.net/browse/PM-23751
+        if (PublicKeyEncryptionKeyPair == null)
+        {
+            return new UserAccountKeysData
+            {
+                PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData
+                (
+                    UserKeyEncryptedAccountPrivateKey,
+                    AccountPublicKey
+                ),
+            };
+        }
+        else
+        {
+            if (SignatureKeyPair == null || SecurityState == null)
+            {
+                return new UserAccountKeysData
+                {
+                    PublicKeyEncryptionKeyPairData = PublicKeyEncryptionKeyPair.ToPublicKeyEncryptionKeyPairData(),
+                };
+            }
+            else
+            {
+                return new UserAccountKeysData
+                {
+                    PublicKeyEncryptionKeyPairData = PublicKeyEncryptionKeyPair.ToPublicKeyEncryptionKeyPairData(),
+                    SignatureKeyPairData = SignatureKeyPair.ToSignatureKeyPairData(),
+                    SecurityStateData = SecurityState.ToSecurityState()
+                };
+            }
+        }
+    }
 }

src/Api/KeyManagement/Models/Requests/KeyRegenerationRequestModel.cs

@@ -1,5 +1,4 @@
-#nullable enable
+using Bit.Core.KeyManagement.Models.Data;
-using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.Utilities;
 
 namespace Bit.Api.KeyManagement.Models.Requests;

src/Api/KeyManagement/Models/Requests/PublicKeyEncryptionKeyPairRequestModel.cs

@@ -0,0 +1,20 @@
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Utilities;
+
+namespace Bit.Api.KeyManagement.Models.Requests;
+
+public class PublicKeyEncryptionKeyPairRequestModel
+{
+    [EncryptedString] public required string WrappedPrivateKey { get; set; }
+    public required string PublicKey { get; set; }
+    public string? SignedPublicKey { get; set; }
+
+    public PublicKeyEncryptionKeyPairData ToPublicKeyEncryptionKeyPairData()
+    {
+        return new PublicKeyEncryptionKeyPairData(
+            WrappedPrivateKey,
+            PublicKey,
+            SignedPublicKey
+        );
+    }
+}

src/Api/KeyManagement/Models/Requests/RotateAccountKeysAndDataRequestModel.cs

@@ -1,5 +1,4 @@
-#nullable enable
+using System.ComponentModel.DataAnnotations;
-using System.ComponentModel.DataAnnotations;
 
 namespace Bit.Api.KeyManagement.Models.Requests;
 

src/Api/KeyManagement/Models/Requests/SignatureKeyPairRequestModel.cs

@@ -0,0 +1,28 @@
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Utilities;
+
+namespace Bit.Api.KeyManagement.Models.Requests;
+
+public class SignatureKeyPairRequestModel
+{
+    public required string SignatureAlgorithm { get; set; }
+    [EncryptedString] public required string WrappedSigningKey { get; set; }
+    public required string VerifyingKey { get; set; }
+
+    public SignatureKeyPairData ToSignatureKeyPairData()
+    {
+        if (SignatureAlgorithm != "ed25519")
+        {
+            throw new ArgumentException(
+                $"Unsupported signature algorithm: {SignatureAlgorithm}"
+            );
+        }
+        var algorithm = Core.KeyManagement.Enums.SignatureAlgorithm.Ed25519;
+
+        return new SignatureKeyPairData(
+            algorithm,
+            WrappedSigningKey,
+            VerifyingKey
+        );
+    }
+}

src/Api/KeyManagement/Models/Requests/UnlockDataRequestModel.cs

@@ -1,5 +1,4 @@
-#nullable enable
+using Bit.Api.AdminConsole.Models.Request.Organizations;
-using Bit.Api.AdminConsole.Models.Request.Organizations;
 using Bit.Api.Auth.Models.Request;
 using Bit.Api.Auth.Models.Request.Accounts;
 using Bit.Api.Auth.Models.Request.WebAuthn;

src/Api/KeyManagement/Models/Requests/UserDataRequestModel.cs

@@ -1,5 +1,4 @@
-#nullable enable
+using Bit.Api.Tools.Models.Request;
-using Bit.Api.Tools.Models.Request;
 using Bit.Api.Vault.Models.Request;
 
 namespace Bit.Api.KeyManagement.Models.Requests;

src/Api/Models/Response/ProfileResponseModel.cs

@@ -5,6 +5,8 @@ using Bit.Api.AdminConsole.Models.Response;
 using Bit.Api.AdminConsole.Models.Response.Providers;
 using Bit.Core.AdminConsole.Models.Data.Provider;
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Models.Api.Response;
+using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.Models.Api;
 using Bit.Core.Models.Data.Organizations.OrganizationUsers;
 
@@ -13,6 +15,7 @@ namespace Bit.Api.Models.Response;
 public class ProfileResponseModel : ResponseModel
 {
     public ProfileResponseModel(User user,
+        UserAccountKeysData userAccountKeysData,
         IEnumerable<OrganizationUserOrganizationDetails> organizationsUserDetails,
         IEnumerable<ProviderUserProviderDetails> providerUserDetails,
         IEnumerable<ProviderUserOrganizationDetails> providerUserOrganizationDetails,
@@ -35,6 +38,7 @@ public class ProfileResponseModel : ResponseModel
         TwoFactorEnabled = twoFactorEnabled;
         Key = user.Key;
         PrivateKey = user.PrivateKey;
+        AccountKeys = userAccountKeysData != null ? new PrivateKeysResponseModel(userAccountKeysData) : null;
         SecurityStamp = user.SecurityStamp;
         ForcePasswordReset = user.ForcePasswordReset;
         UsesKeyConnector = user.UsesKeyConnector;
@@ -60,7 +64,9 @@ public class ProfileResponseModel : ResponseModel
     public string Culture { get; set; }
     public bool TwoFactorEnabled { get; set; }
     public string Key { get; set; }
+    [Obsolete("Use AccountKeys instead.")]
     public string PrivateKey { get; set; }
+    public PrivateKeysResponseModel AccountKeys { get; set; }
     public string SecurityStamp { get; set; }
     public bool ForcePasswordReset { get; set; }
     public bool UsesKeyConnector { get; set; }

src/Api/Vault/Controllers/SyncController.cs

@@ -11,6 +11,8 @@ using Bit.Core.Context;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Data;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -42,6 +44,7 @@ public class SyncController : Controller
     private readonly IFeatureService _featureService;
     private readonly IApplicationCacheService _applicationCacheService;
     private readonly ITwoFactorIsEnabledQuery _twoFactorIsEnabledQuery;
+    private readonly IUserAccountKeysQuery _userAccountKeysQuery;
 
     public SyncController(
         IUserService userService,
@@ -57,7 +60,8 @@ public class SyncController : Controller
         ICurrentContext currentContext,
         IFeatureService featureService,
         IApplicationCacheService applicationCacheService,
-        ITwoFactorIsEnabledQuery twoFactorIsEnabledQuery)
+        ITwoFactorIsEnabledQuery twoFactorIsEnabledQuery,
+        IUserAccountKeysQuery userAccountKeysQuery)
     {
         _userService = userService;
         _folderRepository = folderRepository;
@@ -73,6 +77,7 @@ public class SyncController : Controller
         _featureService = featureService;
         _applicationCacheService = applicationCacheService;
         _twoFactorIsEnabledQuery = twoFactorIsEnabledQuery;
+        _userAccountKeysQuery = userAccountKeysQuery;
     }
 
     [HttpGet("")]
@@ -116,7 +121,14 @@ public class SyncController : Controller
 
         var organizationAbilities = await _applicationCacheService.GetOrganizationAbilitiesAsync();
 
-        var response = new SyncResponseModel(_globalSettings, user, userTwoFactorEnabled, userHasPremiumFromOrganization, organizationAbilities,
+        UserAccountKeysData userAccountKeys = null;
+        // JIT TDE users and some broken/old users may not have a private key.
+        if (!string.IsNullOrWhiteSpace(user.PrivateKey))
+        {
+            userAccountKeys = await _userAccountKeysQuery.Run(user);
+        }
+
+        var response = new SyncResponseModel(_globalSettings, user, userAccountKeys, userTwoFactorEnabled, userHasPremiumFromOrganization, organizationAbilities,
             organizationIdsClaimingActiveUser, organizationUserDetails, providerUserDetails, providerUserOrganizationDetails,
             folders, collections, ciphers, collectionCiphersGroupDict, excludeDomains, policies, sends);
         return response;

src/Api/Vault/Models/Response/SyncResponseModel.cs

@@ -7,7 +7,8 @@ using Bit.Api.Tools.Models.Response;
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.AdminConsole.Models.Data.Provider;
 using Bit.Core.Entities;
-using Bit.Core.KeyManagement.Models.Response;
+using Bit.Core.KeyManagement.Models.Api.Response;
+using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.Models.Api;
 using Bit.Core.Models.Data;
 using Bit.Core.Models.Data.Organizations;
@@ -24,6 +25,7 @@ public class SyncResponseModel() : ResponseModel("sync")
     public SyncResponseModel(
         GlobalSettings globalSettings,
         User user,
+        UserAccountKeysData userAccountKeysData,
         bool userTwoFactorEnabled,
         bool userHasPremiumFromOrganization,
         IDictionary<Guid, OrganizationAbility> organizationAbilities,
@@ -40,7 +42,7 @@ public class SyncResponseModel() : ResponseModel("sync")
         IEnumerable<Send> sends)
         : this()
     {
-        Profile = new ProfileResponseModel(user, organizationUserDetails, providerUserDetails,
+        Profile = new ProfileResponseModel(user, userAccountKeysData, organizationUserDetails, providerUserDetails,
             providerUserOrganizationDetails, userTwoFactorEnabled, userHasPremiumFromOrganization, organizationIdsClaimingingUser);
         Folders = folders.Select(f => new FolderResponseModel(f));
         Ciphers = ciphers.Select(cipher =>

src/Core/Auth/Models/Api/Response/UserDecryptionOptions.cs

@@ -1,5 +1,5 @@
 using System.Text.Json.Serialization;
-using Bit.Core.KeyManagement.Models.Response;
+using Bit.Core.KeyManagement.Models.Api.Response;
 using Bit.Core.Models.Api;
 
 namespace Bit.Core.Auth.Models.Api.Response;

src/Core/Constants.cs

@@ -192,6 +192,7 @@ public static class FeatureFlagKeys
     public const string UserkeyRotationV2 = "userkey-rotation-v2";
     public const string SSHKeyItemVaultItem = "ssh-key-vault-item";
     public const string UserSdkForDecryption = "use-sdk-for-decryption";
+    public const string EnrollAeadOnKeyRotation = "enroll-aead-on-key-rotation";
     public const string PM17987_BlockType0 = "pm-17987-block-type-0";
     public const string ForceUpdateKDFSettings = "pm-18021-force-update-kdf-settings";
     public const string UnlockWithMasterPasswordUnlockData = "pm-23246-unlock-with-master-password-unlock-data";

src/Core/Entities/User.cs

@@ -3,6 +3,7 @@ using System.Text.Json;
 using Bit.Core.Auth.Enums;
 using Bit.Core.Auth.Models;
 using Bit.Core.Enums;
+using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.Utilities;
 using Microsoft.AspNetCore.Identity;
 
@@ -21,6 +22,9 @@ public class User : ITableObject<Guid>, IStorableSubscriber, IRevisable, ITwoFac
     [MaxLength(256)]
     public string Email { get; set; } = null!;
     public bool EmailVerified { get; set; }
+    /// <summary>
+    /// The server-side master-password hash
+    /// </summary>
     [MaxLength(300)]
     public string? MasterPassword { get; set; }
     [MaxLength(50)]
@@ -41,9 +45,30 @@ public class User : ITableObject<Guid>, IStorableSubscriber, IRevisable, ITwoFac
     /// organization membership.
     /// </summary>
     public DateTime AccountRevisionDate { get; set; } = DateTime.UtcNow;
+    /// <summary>
+    /// The master-password-sealed user key.
+    /// </summary>
     public string? Key { get; set; }
+    /// <summary>
+    /// The raw public key, without a signature from the user's signature key.
+    /// </summary> 
     public string? PublicKey { get; set; }
+    /// <summary>
+    /// User key wrapped private key.
+    /// </summary>
     public string? PrivateKey { get; set; }
+    /// <summary>
+    /// The public key, signed by the user's signature key.
+    /// </summary>
+    public string? SignedPublicKey { get; set; }
+    /// <summary>
+    /// The security version is included in the security state, but needs COSE parsing
+    /// </summary>
+    public int? SecurityVersion { get; set; }
+    /// <summary>
+    /// The security state is a signed object attesting to the version of the user's account.
+    /// </summary>
+    public string? SecurityState { get; set; }
     public bool Premium { get; set; }
     public DateTime? PremiumExpirationDate { get; set; }
     public DateTime? RenewalReminderDate { get; set; }
@@ -180,6 +205,12 @@ public class User : ITableObject<Guid>, IStorableSubscriber, IRevisable, ITwoFac
         return Premium;
     }
 
+    public int GetSecurityVersion()
+    {
+        // If no security version is set, it is version 1. The minimum initialized version is 2.
+        return SecurityVersion ?? 1;
+    }
+
     /// <summary>
     /// Serializes the C# object to the User.TwoFactorProviders property in JSON format.
     /// </summary>
@@ -243,4 +274,14 @@ public class User : ITableObject<Guid>, IStorableSubscriber, IRevisable, ITwoFac
     {
         return MasterPassword != null;
     }
+
+    public PublicKeyEncryptionKeyPairData GetPublicKeyEncryptionKeyPair()
+    {
+        if (string.IsNullOrWhiteSpace(PrivateKey) || string.IsNullOrWhiteSpace(PublicKey))
+        {
+            throw new InvalidOperationException("User public key encryption key pair is not fully initialized.");
+        }
+
+        return new PublicKeyEncryptionKeyPairData(PrivateKey, PublicKey, SignedPublicKey);
+    }
 }

src/Core/KeyManagement/Entities/UserSignatureKeyPair.cs

@@ -0,0 +1,30 @@
+using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Enums;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Utilities;
+
+
+namespace Bit.Core.KeyManagement.Entities;
+
+public class UserSignatureKeyPair : ITableObject<Guid>, IRevisable
+{
+    public Guid Id { get; set; }
+    public Guid UserId { get; set; }
+    public SignatureAlgorithm SignatureAlgorithm { get; set; }
+
+    public required string VerifyingKey { get; set; }
+    public required string SigningKey { get; set; }
+
+    public DateTime CreationDate { get; set; } = DateTime.UtcNow;
+    public DateTime RevisionDate { get; set; } = DateTime.UtcNow;
+
+    public void SetNewId()
+    {
+        Id = CoreHelpers.GenerateComb();
+    }
+
+    public SignatureKeyPairData ToSignatureKeyPairData()
+    {
+        return new SignatureKeyPairData(SignatureAlgorithm, SigningKey, VerifyingKey);
+    }
+}

src/Core/KeyManagement/Enums/SignatureAlgorithm.cs

@@ -0,0 +1,9 @@
+namespace Bit.Core.KeyManagement.Enums;
+
+// <summary>
+// Represents the algorithm / digital signature scheme used for a signature key pair.
+// </summary>
+public enum SignatureAlgorithm : byte
+{
+    Ed25519 = 0
+}

src/Core/KeyManagement/KeyManagementServiceCollectionExtensions.cs

@@ -2,6 +2,8 @@
 using Bit.Core.KeyManagement.Commands.Interfaces;
 using Bit.Core.KeyManagement.Kdf;
 using Bit.Core.KeyManagement.Kdf.Implementations;
+using Bit.Core.KeyManagement.Queries;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Microsoft.Extensions.DependencyInjection;
 
 namespace Bit.Core.KeyManagement;
@@ -11,6 +13,7 @@ public static class KeyManagementServiceCollectionExtensions
     public static void AddKeyManagementServices(this IServiceCollection services)
     {
         services.AddKeyManagementCommands();
+        services.AddKeyManagementQueries();
         services.AddSendPasswordServices();
     }
 
@@ -19,4 +22,9 @@ public static class KeyManagementServiceCollectionExtensions
         services.AddScoped<IRegenerateUserAsymmetricKeysCommand, RegenerateUserAsymmetricKeysCommand>();
         services.AddScoped<IChangeKdfCommand, ChangeKdfCommand>();
     }
+
+    private static void AddKeyManagementQueries(this IServiceCollection services)
+    {
+        services.AddScoped<IUserAccountKeysQuery, UserAccountKeysQuery>();
+    }
 }

src/Core/KeyManagement/Models/Api/Request/SecurityStateModel.cs

@@ -0,0 +1,32 @@
+using System.ComponentModel.DataAnnotations;
+using System.Text.Json.Serialization;
+using Bit.Core.KeyManagement.Models.Data;
+
+namespace Bit.Core.KeyManagement.Models.Api.Request;
+
+public class SecurityStateModel
+{
+    [StringLength(1000)]
+    [JsonPropertyName("securityState")]
+    public required string SecurityState { get; set; }
+    [JsonPropertyName("securityVersion")]
+    public required int SecurityVersion { get; set; }
+
+    public SecurityStateData ToSecurityState()
+    {
+        return new SecurityStateData
+        {
+            SecurityState = SecurityState,
+            SecurityVersion = SecurityVersion
+        };
+    }
+
+    public static SecurityStateModel FromSecurityStateData(SecurityStateData data)
+    {
+        return new SecurityStateModel
+        {
+            SecurityState = data.SecurityState,
+            SecurityVersion = data.SecurityVersion
+        };
+    }
+}

src/Core/KeyManagement/Models/Api/Response/MasterPasswordUnlockResponseModel.cs

@@ -2,7 +2,7 @@
 using Bit.Core.Enums;
 using Bit.Core.Utilities;
 
-namespace Bit.Core.KeyManagement.Models.Response;
+namespace Bit.Core.KeyManagement.Models.Api.Response;
 
 public class MasterPasswordUnlockResponseModel
 {

src/Core/KeyManagement/Models/Api/Response/PrivateKeysResponseModel.cs

@@ -0,0 +1,48 @@
+using System.Text.Json.Serialization;
+using Bit.Core.KeyManagement.Models.Api.Request;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Models.Api;
+
+namespace Bit.Core.KeyManagement.Models.Api.Response;
+
+
+/// <summary>
+/// This response model is used to return the asymmetric encryption keys,
+/// and signature keys of an entity. This includes the private keys of the key pairs,
+/// (private key, signing key), and the public keys of the key pairs (unsigned public key,
+/// signed public key, verification key). 
+/// </summary>
+public class PrivateKeysResponseModel : ResponseModel
+{
+    // Not all accounts have signature keys, but all accounts have public encryption keys.
+    [JsonPropertyName("signatureKeyPair")]
+    public SignatureKeyPairResponseModel? SignatureKeyPair { get; set; }
+
+    [JsonPropertyName("publicKeyEncryptionKeyPair")]
+    public required PublicKeyEncryptionKeyPairResponseModel PublicKeyEncryptionKeyPair { get; set; }
+
+    [JsonPropertyName("securityState")]
+    public SecurityStateModel? SecurityState { get; set; }
+
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public PrivateKeysResponseModel(UserAccountKeysData accountKeys) : base("privateKeys")
+    {
+        ArgumentNullException.ThrowIfNull(accountKeys);
+        PublicKeyEncryptionKeyPair = new PublicKeyEncryptionKeyPairResponseModel(accountKeys.PublicKeyEncryptionKeyPairData);
+
+        if (accountKeys.SignatureKeyPairData != null && accountKeys.SecurityStateData != null)
+        {
+            SignatureKeyPair = new SignatureKeyPairResponseModel(accountKeys.SignatureKeyPairData);
+            SecurityState = SecurityStateModel.FromSecurityStateData(accountKeys.SecurityStateData!);
+        }
+    }
+
+    [JsonConstructor]
+    public PrivateKeysResponseModel(SignatureKeyPairResponseModel? signatureKeyPair, PublicKeyEncryptionKeyPairResponseModel publicKeyEncryptionKeyPair, SecurityStateModel? securityState)
+        : base("privateKeys")
+    {
+        SignatureKeyPair = signatureKeyPair;
+        PublicKeyEncryptionKeyPair = publicKeyEncryptionKeyPair ?? throw new ArgumentNullException(nameof(publicKeyEncryptionKeyPair));
+        SecurityState = securityState;
+    }
+}

src/Core/KeyManagement/Models/Api/Response/PublicKeyEncryptionKeyPairResponseModel.cs

@@ -0,0 +1,34 @@
+using System.Text.Json.Serialization;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Models.Api;
+
+namespace Bit.Core.KeyManagement.Models.Api.Response;
+
+
+public class PublicKeyEncryptionKeyPairResponseModel : ResponseModel
+{
+    [JsonPropertyName("wrappedPrivateKey")]
+    public required string WrappedPrivateKey { get; set; }
+    [JsonPropertyName("publicKey")]
+    public required string PublicKey { get; set; }
+    [JsonPropertyName("signedPublicKey")]
+    public string? SignedPublicKey { get; set; }
+
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public PublicKeyEncryptionKeyPairResponseModel(PublicKeyEncryptionKeyPairData keyPair)
+        : base("publicKeyEncryptionKeyPair")
+    {
+        WrappedPrivateKey = keyPair.WrappedPrivateKey;
+        PublicKey = keyPair.PublicKey;
+        SignedPublicKey = keyPair.SignedPublicKey;
+    }
+
+    [JsonConstructor]
+    public PublicKeyEncryptionKeyPairResponseModel(string wrappedPrivateKey, string publicKey, string? signedPublicKey)
+        : base("publicKeyEncryptionKeyPair")
+    {
+        WrappedPrivateKey = wrappedPrivateKey ?? throw new ArgumentNullException(nameof(wrappedPrivateKey));
+        PublicKey = publicKey ?? throw new ArgumentNullException(nameof(publicKey));
+        SignedPublicKey = signedPublicKey;
+    }
+}

src/Core/KeyManagement/Models/Api/Response/PublicKeysResponseModel.cs

@@ -0,0 +1,30 @@
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Models.Api;
+
+namespace Bit.Core.KeyManagement.Models.Api.Response;
+
+
+/// <summary>
+/// This response model is used to return the public keys of a user, to any other registered user or entity on the server.
+/// It can contain public keys (signature/encryption), and proofs between the two. It does not contain (encrypted) private keys.
+/// </summary>
+public class PublicKeysResponseModel : ResponseModel
+{
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public PublicKeysResponseModel(UserAccountKeysData accountKeys)
+        : base("publicKeys")
+    {
+        ArgumentNullException.ThrowIfNull(accountKeys);
+        PublicKey = accountKeys.PublicKeyEncryptionKeyPairData.PublicKey;
+
+        if (accountKeys.SignatureKeyPairData != null)
+        {
+            SignedPublicKey = accountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey;
+            VerifyingKey = accountKeys.SignatureKeyPairData.VerifyingKey;
+        }
+    }
+
+    public string? VerifyingKey { get; set; }
+    public string? SignedPublicKey { get; set; }
+    public required string PublicKey { get; set; }
+}

src/Core/KeyManagement/Models/Api/Response/SignatureKeyPairResponseModel.cs

@@ -0,0 +1,32 @@
+using System.Text.Json.Serialization;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Models.Api;
+
+namespace Bit.Core.KeyManagement.Models.Api.Response;
+
+
+public class SignatureKeyPairResponseModel : ResponseModel
+{
+    [JsonPropertyName("wrappedSigningKey")]
+    public required string WrappedSigningKey { get; set; }
+    [JsonPropertyName("verifyingKey")]
+    public required string VerifyingKey { get; set; }
+
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public SignatureKeyPairResponseModel(SignatureKeyPairData signatureKeyPair)
+        : base("signatureKeyPair")
+    {
+        ArgumentNullException.ThrowIfNull(signatureKeyPair);
+        WrappedSigningKey = signatureKeyPair.WrappedSigningKey;
+        VerifyingKey = signatureKeyPair.VerifyingKey;
+    }
+
+
+    [JsonConstructor]
+    public SignatureKeyPairResponseModel(string wrappedSigningKey, string verifyingKey)
+        : base("signatureKeyPair")
+    {
+        WrappedSigningKey = wrappedSigningKey ?? throw new ArgumentNullException(nameof(wrappedSigningKey));
+        VerifyingKey = verifyingKey ?? throw new ArgumentNullException(nameof(verifyingKey));
+    }
+}

src/Core/KeyManagement/Models/Api/Response/UserDecryptionResponseModel.cs

@@ -1,4 +1,4 @@
-namespace Bit.Core.KeyManagement.Models.Response;
+namespace Bit.Core.KeyManagement.Models.Api.Response;
 
 public class UserDecryptionResponseModel
 {

src/Core/KeyManagement/Models/Data/PublicKeyEncryptionKeyPairData.cs

@@ -0,0 +1,20 @@
+using System.Text.Json.Serialization;
+
+namespace Bit.Core.KeyManagement.Models.Data;
+
+
+public class PublicKeyEncryptionKeyPairData
+{
+    public required string WrappedPrivateKey { get; set; }
+    public string? SignedPublicKey { get; set; }
+    public required string PublicKey { get; set; }
+
+    [JsonConstructor]
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public PublicKeyEncryptionKeyPairData(string wrappedPrivateKey, string publicKey, string? signedPublicKey = null)
+    {
+        WrappedPrivateKey = wrappedPrivateKey ?? throw new ArgumentNullException(nameof(wrappedPrivateKey));
+        PublicKey = publicKey ?? throw new ArgumentNullException(nameof(publicKey));
+        SignedPublicKey = signedPublicKey;
+    }
+}

src/Core/KeyManagement/Models/Data/RotateUserAccountKeysData.cs

@@ -1,6 +1,4 @@
-// FIXME: Update this file to be null safe and then delete the line below
+
-#nullable disable
-
 using Bit.Core.Auth.Entities;
 using Bit.Core.Auth.Models.Data;
 using Bit.Core.Entities;
@@ -12,21 +10,19 @@ namespace Bit.Core.KeyManagement.Models.Data;
 public class RotateUserAccountKeysData
 {
     // Authentication for this requests
-    public string OldMasterKeyAuthenticationHash { get; set; }
+    public required string OldMasterKeyAuthenticationHash { get; set; }
 
-    // Other keys encrypted by the userkey
+    public required UserAccountKeysData AccountKeys { get; set; }
-    public string UserKeyEncryptedAccountPrivateKey { get; set; }
-    public string AccountPublicKey { get; set; }
 
     // All methods to get to the userkey
-    public MasterPasswordUnlockAndAuthenticationData MasterPasswordUnlockData { get; set; }
+    public required MasterPasswordUnlockAndAuthenticationData MasterPasswordUnlockData { get; set; }
-    public IEnumerable<EmergencyAccess> EmergencyAccesses { get; set; }
+    public required IEnumerable<EmergencyAccess> EmergencyAccesses { get; set; }
-    public IReadOnlyList<OrganizationUser> OrganizationUsers { get; set; }
+    public required IReadOnlyList<OrganizationUser> OrganizationUsers { get; set; }
-    public IEnumerable<WebAuthnLoginRotateKeyData> WebAuthnKeys { get; set; }
+    public required IEnumerable<WebAuthnLoginRotateKeyData> WebAuthnKeys { get; set; }
-    public IEnumerable<Device> DeviceKeys { get; set; }
+    public required IEnumerable<Device> DeviceKeys { get; set; }
 
     // User vault data encrypted by the userkey
-    public IEnumerable<Cipher> Ciphers { get; set; }
+    public required IEnumerable<Cipher> Ciphers { get; set; }
-    public IEnumerable<Folder> Folders { get; set; }
+    public required IEnumerable<Folder> Folders { get; set; }
-    public IReadOnlyList<Send> Sends { get; set; }
+    public required IReadOnlyList<Send> Sends { get; set; }
 }

src/Core/KeyManagement/Models/Data/SecurityStateData.cs

@@ -0,0 +1,10 @@
+
+namespace Bit.Core.KeyManagement.Models.Data;
+
+public class SecurityStateData
+{
+    public required string SecurityState { get; set; }
+    // The security version is included in the security state, but needs COSE parsing,
+    // so this is a separate copy that can be used directly.
+    public required int SecurityVersion { get; set; }
+}

src/Core/KeyManagement/Models/Data/SignatureKeyPairData.cs

@@ -0,0 +1,21 @@
+
+using System.Text.Json.Serialization;
+using Bit.Core.KeyManagement.Enums;
+
+namespace Bit.Core.KeyManagement.Models.Data;
+
+public class SignatureKeyPairData
+{
+    public required SignatureAlgorithm SignatureAlgorithm { get; set; }
+    public required string WrappedSigningKey { get; set; }
+    public required string VerifyingKey { get; set; }
+
+    [JsonConstructor]
+    [System.Diagnostics.CodeAnalysis.SetsRequiredMembersAttribute]
+    public SignatureKeyPairData(SignatureAlgorithm signatureAlgorithm, string wrappedSigningKey, string verifyingKey)
+    {
+        SignatureAlgorithm = signatureAlgorithm;
+        WrappedSigningKey = wrappedSigningKey ?? throw new ArgumentNullException(nameof(wrappedSigningKey));
+        VerifyingKey = verifyingKey ?? throw new ArgumentNullException(nameof(verifyingKey));
+    }
+}

src/Core/KeyManagement/Models/Data/UserAccountKeysData.cs

@@ -0,0 +1,9 @@
+namespace Bit.Core.KeyManagement.Models.Data;
+
+
+public class UserAccountKeysData
+{
+    public required PublicKeyEncryptionKeyPairData PublicKeyEncryptionKeyPairData { get; set; }
+    public SignatureKeyPairData? SignatureKeyPairData { get; set; }
+    public SecurityStateData? SecurityStateData { get; set; }
+}

src/Core/KeyManagement/Queries/Interfaces/IUserAcountKeysQuery.cs

@@ -0,0 +1,10 @@
+
+using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+
+namespace Bit.Core.KeyManagement.Queries.Interfaces;
+
+public interface IUserAccountKeysQuery
+{
+    Task<UserAccountKeysData> Run(User user);
+}

src/Core/KeyManagement/Queries/UserAccountKeysQuery.cs

@@ -0,0 +1,35 @@
+
+using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries.Interfaces;
+using Bit.Core.KeyManagement.Repositories;
+
+namespace Bit.Core.KeyManagement.Queries;
+
+
+public class UserAccountKeysQuery(IUserSignatureKeyPairRepository signatureKeyPairRepository) : IUserAccountKeysQuery
+{
+    public async Task<UserAccountKeysData> Run(User user)
+    {
+        if (user.GetSecurityVersion() < 2)
+        {
+            return new UserAccountKeysData
+            {
+                PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            };
+        }
+        else
+        {
+            return new UserAccountKeysData
+            {
+                PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+                SignatureKeyPairData = await signatureKeyPairRepository.GetByUserIdAsync(user.Id),
+                SecurityStateData = new SecurityStateData
+                {
+                    SecurityState = user.SecurityState!,
+                    SecurityVersion = user.GetSecurityVersion(),
+                }
+            };
+        }
+    }
+}

src/Core/KeyManagement/Repositories/IUserSignatureKeyPairRepository.cs

@@ -0,0 +1,14 @@
+
+using Bit.Core.KeyManagement.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.UserKey;
+using Bit.Core.Repositories;
+
+namespace Bit.Core.KeyManagement.Repositories;
+
+public interface IUserSignatureKeyPairRepository : IRepository<UserSignatureKeyPair, Guid>
+{
+    public Task<SignatureKeyPairData?> GetByUserIdAsync(Guid userId);
+    public UpdateEncryptedDataForKeyRotation UpdateForKeyRotation(Guid grantorId, SignatureKeyPairData signatureKeyPair);
+    public UpdateEncryptedDataForKeyRotation SetUserSignatureKeyPair(Guid userId, SignatureKeyPairData signatureKeyPair);
+}

src/Core/KeyManagement/UserKey/Implementations/RotateUserAccountkeysCommand.cs

@@ -1,6 +1,11 @@
-using Bit.Core.Auth.Repositories;
+// FIXME: Update this file to be null safe and then delete the line below
+#nullable disable
+
+using Bit.Core.Auth.Repositories;
 using Bit.Core.Entities;
+using Bit.Core.Enums;
 using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Repositories;
 using Bit.Core.Platform.Push;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -25,6 +30,8 @@ public class RotateUserAccountKeysCommand : IRotateUserAccountKeysCommand
     private readonly IdentityErrorDescriber _identityErrorDescriber;
     private readonly IWebAuthnCredentialRepository _credentialRepository;
     private readonly IPasswordHasher<User> _passwordHasher;
+    private readonly IUserSignatureKeyPairRepository _userSignatureKeyPairRepository;
+    private readonly IFeatureService _featureService;
 
     /// <summary>
     /// Instantiates a new <see cref="RotateUserAccountKeysCommand"/>
@@ -36,16 +43,19 @@ public class RotateUserAccountKeysCommand : IRotateUserAccountKeysCommand
     /// <param name="sendRepository">Provides a method to update re-encrypted send data</param>
     /// <param name="emergencyAccessRepository">Provides a method to update re-encrypted emergency access data</param>
     /// <param name="organizationUserRepository">Provides a method to update re-encrypted organization user data</param>
+    /// <param name="deviceRepository">Provides a method to update re-encrypted device keys</param>
     /// <param name="passwordHasher">Hashes the new master password</param>
     /// <param name="pushService">Logs out user from other devices after successful rotation</param>
     /// <param name="errors">Provides a password mismatch error if master password hash validation fails</param>
     /// <param name="credentialRepository">Provides a method to update re-encrypted WebAuthn keys</param>
+    /// <param name="userSignatureKeyPairRepository">Provides a method to update re-encrypted signature keys</param>
     public RotateUserAccountKeysCommand(IUserService userService, IUserRepository userRepository,
         ICipherRepository cipherRepository, IFolderRepository folderRepository, ISendRepository sendRepository,
         IEmergencyAccessRepository emergencyAccessRepository, IOrganizationUserRepository organizationUserRepository,
         IDeviceRepository deviceRepository,
         IPasswordHasher<User> passwordHasher,
         IPushNotificationService pushService, IdentityErrorDescriber errors, IWebAuthnCredentialRepository credentialRepository,
+        IUserSignatureKeyPairRepository userSignatureKeyPairRepository,
         IFeatureService featureService)
     {
         _userService = userService;
@@ -60,6 +70,8 @@ public class RotateUserAccountKeysCommand : IRotateUserAccountKeysCommand
         _identityErrorDescriber = errors;
         _credentialRepository = credentialRepository;
         _passwordHasher = passwordHasher;
+        _userSignatureKeyPairRepository = userSignatureKeyPairRepository;
+        _featureService = featureService;
     }
 
     /// <inheritdoc />
@@ -80,50 +92,106 @@ public class RotateUserAccountKeysCommand : IRotateUserAccountKeysCommand
         user.LastKeyRotationDate = now;
         user.SecurityStamp = Guid.NewGuid().ToString();
 
-        if (
+        List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions = [];
-            !model.MasterPasswordUnlockData.ValidateForUser(user)
+
-        )
+        await UpdateAccountKeysAsync(model, user, saveEncryptedDataActions);
-        {
+        UpdateUnlockMethods(model, user, saveEncryptedDataActions);
-            throw new InvalidOperationException("The provided master password unlock data is not valid for this user.");
+        UpdateUserData(model, user, saveEncryptedDataActions);
-        }
+
-        if (
+        await _userRepository.UpdateUserKeyAndEncryptedDataV2Async(user, saveEncryptedDataActions);
-            model.AccountPublicKey != user.PublicKey
+        await _pushService.PushLogOutAsync(user.Id);
-        )
+        return IdentityResult.Success;
-        {
-            throw new InvalidOperationException("The provided account public key does not match the user's current public key, and changing the account asymmetric keypair is currently not supported during key rotation.");
     }
 
-        user.Key = model.MasterPasswordUnlockData.MasterKeyEncryptedUserKey;
+    public async Task RotateV2AccountKeysAsync(RotateUserAccountKeysData model, User user, List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions)
-        user.PrivateKey = model.UserKeyEncryptedAccountPrivateKey;
+    {
-        user.MasterPassword = _passwordHasher.HashPassword(user, model.MasterPasswordUnlockData.MasterKeyAuthenticationHash);
+        ValidateV2Encryption(model);
-        user.MasterPasswordHint = model.MasterPasswordUnlockData.MasterPasswordHint;
+        await ValidateVerifyingKeyUnchangedAsync(model, user);
+
+        saveEncryptedDataActions.Add(_userSignatureKeyPairRepository.UpdateForKeyRotation(user.Id, model.AccountKeys.SignatureKeyPairData));
+        user.SignedPublicKey = model.AccountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey;
+        user.SecurityState = model.AccountKeys.SecurityStateData!.SecurityState;
+        user.SecurityVersion = model.AccountKeys.SecurityStateData.SecurityVersion;
+    }
+
+    public void UpgradeV1ToV2Keys(RotateUserAccountKeysData model, User user, List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions)
+    {
+        ValidateV2Encryption(model);
+        saveEncryptedDataActions.Add(_userSignatureKeyPairRepository.SetUserSignatureKeyPair(user.Id, model.AccountKeys.SignatureKeyPairData));
+        user.SignedPublicKey = model.AccountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey;
+        user.SecurityState = model.AccountKeys.SecurityStateData!.SecurityState;
+        user.SecurityVersion = model.AccountKeys.SecurityStateData.SecurityVersion;
+    }
+
+    public async Task UpdateAccountKeysAsync(RotateUserAccountKeysData model, User user, List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions)
+    {
+        ValidatePublicKeyEncryptionKeyPairUnchanged(model, user);
+
+        if (IsV2EncryptionUserAsync(user))
+        {
+            await RotateV2AccountKeysAsync(model, user, saveEncryptedDataActions);
+        }
+        else if (model.AccountKeys.SignatureKeyPairData != null)
+        {
+            UpgradeV1ToV2Keys(model, user, saveEncryptedDataActions);
+        }
+        else
+        {
+            if (GetEncryptionType(model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey) != EncryptionType.AesCbc256_HmacSha256_B64)
+            {
+                throw new InvalidOperationException("The provided account private key was not wrapped with AES-256-CBC-HMAC");
+            }
+            // V1 user to V1 user rotation needs to further changes, the private key was re-encrypted.
+        }
+
+        // Private key is re-wrapped with new user key by client
+        user.PrivateKey = model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey;
+    }
+
+    public void UpdateUserData(RotateUserAccountKeysData model, User user, List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions)
+    {
+        // The revision date has to be updated so that de-synced clients don't accidentally post over the re-encrypted data
+        // with an old-user key-encrypted copy
+        var now = DateTime.UtcNow;
 
-        List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions = new();
         if (model.Ciphers.Any())
         {
-            saveEncryptedDataActions.Add(_cipherRepository.UpdateForKeyRotation(user.Id, model.Ciphers));
+            var ciphersWithUpdatedDate = model.Ciphers.ToList().Select(c => { c.RevisionDate = now; return c; });
+            saveEncryptedDataActions.Add(_cipherRepository.UpdateForKeyRotation(user.Id, ciphersWithUpdatedDate));
         }
 
         if (model.Folders.Any())
         {
-            saveEncryptedDataActions.Add(_folderRepository.UpdateForKeyRotation(user.Id, model.Folders));
+            var foldersWithUpdatedDate = model.Folders.ToList().Select(f => { f.RevisionDate = now; return f; });
+            saveEncryptedDataActions.Add(_folderRepository.UpdateForKeyRotation(user.Id, foldersWithUpdatedDate));
         }
 
         if (model.Sends.Any())
         {
-            saveEncryptedDataActions.Add(_sendRepository.UpdateForKeyRotation(user.Id, model.Sends));
+            var sendsWithUpdatedDate = model.Sends.ToList().Select(s => { s.RevisionDate = now; return s; });
+            saveEncryptedDataActions.Add(_sendRepository.UpdateForKeyRotation(user.Id, sendsWithUpdatedDate));
         }
+    }
+
+    void UpdateUnlockMethods(RotateUserAccountKeysData model, User user, List<UpdateEncryptedDataForKeyRotation> saveEncryptedDataActions)
+    {
+        if (!model.MasterPasswordUnlockData.ValidateForUser(user))
+        {
+            throw new InvalidOperationException("The provided master password unlock data is not valid for this user.");
+        }
+        // Update master password authentication & unlock
+        user.Key = model.MasterPasswordUnlockData.MasterKeyEncryptedUserKey;
+        user.MasterPassword = _passwordHasher.HashPassword(user, model.MasterPasswordUnlockData.MasterKeyAuthenticationHash);
+        user.MasterPasswordHint = model.MasterPasswordUnlockData.MasterPasswordHint;
 
         if (model.EmergencyAccesses.Any())
         {
-            saveEncryptedDataActions.Add(
+            saveEncryptedDataActions.Add(_emergencyAccessRepository.UpdateForKeyRotation(user.Id, model.EmergencyAccesses));
-                _emergencyAccessRepository.UpdateForKeyRotation(user.Id, model.EmergencyAccesses));
         }
 
         if (model.OrganizationUsers.Any())
         {
-            saveEncryptedDataActions.Add(
+            saveEncryptedDataActions.Add(_organizationUserRepository.UpdateForKeyRotation(user.Id, model.OrganizationUsers));
-                _organizationUserRepository.UpdateForKeyRotation(user.Id, model.OrganizationUsers));
         }
 
         if (model.WebAuthnKeys.Any())
@@ -135,9 +203,80 @@ public class RotateUserAccountKeysCommand : IRotateUserAccountKeysCommand
         {
             saveEncryptedDataActions.Add(_deviceRepository.UpdateKeysForRotationAsync(user.Id, model.DeviceKeys));
         }
+    }
 
-        await _userRepository.UpdateUserKeyAndEncryptedDataV2Async(user, saveEncryptedDataActions);
+    private bool IsV2EncryptionUserAsync(User user)
-        await _pushService.PushLogOutAsync(user.Id);
+    {
-        return IdentityResult.Success;
+        // Returns whether the user is a V2 user based on the private key's encryption type.
+        ArgumentNullException.ThrowIfNull(user);
+        var isPrivateKeyEncryptionV2 = GetEncryptionType(user.PrivateKey) == EncryptionType.XChaCha20Poly1305_B64;
+        return isPrivateKeyEncryptionV2;
+    }
+
+    private async Task ValidateVerifyingKeyUnchangedAsync(RotateUserAccountKeysData model, User user)
+    {
+        var currentSignatureKeyPair = await _userSignatureKeyPairRepository.GetByUserIdAsync(user.Id) ?? throw new InvalidOperationException("User does not have a signature key pair.");
+        if (model.AccountKeys.SignatureKeyPairData.VerifyingKey != currentSignatureKeyPair!.VerifyingKey)
+        {
+            throw new InvalidOperationException("The provided verifying key does not match the user's current verifying key.");
+        }
+    }
+
+    private static void ValidatePublicKeyEncryptionKeyPairUnchanged(RotateUserAccountKeysData model, User user)
+    {
+        var publicKey = model.AccountKeys.PublicKeyEncryptionKeyPairData.PublicKey;
+        if (publicKey != user.PublicKey)
+        {
+            throw new InvalidOperationException("The provided account public key does not match the user's current public key, and changing the account asymmetric key pair is currently not supported during key rotation.");
+        }
+    }
+
+    private static void ValidateV2Encryption(RotateUserAccountKeysData model)
+    {
+        if (model.AccountKeys.SignatureKeyPairData == null)
+        {
+            throw new InvalidOperationException("Signature key pair data is required for V2 encryption.");
+        }
+        if (GetEncryptionType(model.AccountKeys.SignatureKeyPairData.WrappedSigningKey) != EncryptionType.XChaCha20Poly1305_B64)
+        {
+            throw new InvalidOperationException("The provided signing key data is not wrapped with XChaCha20-Poly1305.");
+        }
+        if (string.IsNullOrEmpty(model.AccountKeys.SignatureKeyPairData.VerifyingKey))
+        {
+            throw new InvalidOperationException("The provided signature key pair data does not contain a valid verifying key.");
+        }
+
+        if (GetEncryptionType(model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey) != EncryptionType.XChaCha20Poly1305_B64)
+        {
+            throw new InvalidOperationException("The provided private key encryption key is not wrapped with XChaCha20-Poly1305.");
+        }
+        if (string.IsNullOrEmpty(model.AccountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey))
+        {
+            throw new InvalidOperationException("No signed public key provided, but the user already has a signature key pair.");
+        }
+        if (model.AccountKeys.SecurityStateData == null || string.IsNullOrEmpty(model.AccountKeys.SecurityStateData.SecurityState))
+        {
+            throw new InvalidOperationException("No signed security state provider for V2 user");
+        }
+    }
+
+    /// <summary>
+    /// Helper method to convert an encryption type string to an enum value.
+    /// </summary>
+    private static EncryptionType GetEncryptionType(string encString)
+    {
+        var parts = encString.Split('.');
+        if (parts.Length == 1)
+        {
+            throw new ArgumentException("Invalid encryption type string.");
+        }
+        if (byte.TryParse(parts[0], out var encryptionTypeNumber))
+        {
+            if (Enum.IsDefined(typeof(EncryptionType), encryptionTypeNumber))
+            {
+                return (EncryptionType)encryptionTypeNumber;
+            }
+        }
+        throw new ArgumentException("Invalid encryption type string.");
     }
 }

src/Identity/IdentityServer/RequestValidators/BaseRequestValidator.cs

@@ -14,6 +14,8 @@ using Bit.Core.Auth.Repositories;
 using Bit.Core.Context;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
+using Bit.Core.KeyManagement.Models.Api.Response;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Api;
 using Bit.Core.Models.Api.Response;
 using Bit.Core.Repositories;
@@ -45,6 +47,7 @@ public abstract class BaseRequestValidator<T> where T : class
     protected IUserService _userService { get; }
     protected IUserDecryptionOptionsBuilder UserDecryptionOptionsBuilder { get; }
     protected IPolicyRequirementQuery PolicyRequirementQuery { get; }
+    protected IUserAccountKeysQuery _accountKeysQuery { get; }
 
     public BaseRequestValidator(
         UserManager<User> userManager,
@@ -63,7 +66,8 @@ public abstract class BaseRequestValidator<T> where T : class
         IUserDecryptionOptionsBuilder userDecryptionOptionsBuilder,
         IPolicyRequirementQuery policyRequirementQuery,
         IAuthRequestRepository authRequestRepository,
-        IMailService mailService
+        IMailService mailService,
+        IUserAccountKeysQuery userAccountKeysQuery
         )
     {
         _userManager = userManager;
@@ -83,6 +87,7 @@ public abstract class BaseRequestValidator<T> where T : class
         PolicyRequirementQuery = policyRequirementQuery;
         _authRequestRepository = authRequestRepository;
         _mailService = mailService;
+        _accountKeysQuery = userAccountKeysQuery;
     }
 
     protected async Task ValidateAsync(T context, ValidatedTokenRequest request,
@@ -439,6 +444,8 @@ public abstract class BaseRequestValidator<T> where T : class
         if (!string.IsNullOrWhiteSpace(user.PrivateKey))
         {
             customResponse.Add("PrivateKey", user.PrivateKey);
+            var accountKeys = await _accountKeysQuery.Run(user);
+            customResponse.Add("AccountKeys", new PrivateKeysResponseModel(accountKeys));
         }
 
         if (!string.IsNullOrWhiteSpace(user.Key))

src/Identity/IdentityServer/RequestValidators/CustomTokenRequestValidator.cs

@@ -8,6 +8,7 @@ using Bit.Core.Auth.Models.Api.Response;
 using Bit.Core.Auth.Repositories;
 using Bit.Core.Context;
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Platform.Installations;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -47,7 +48,8 @@ public class CustomTokenRequestValidator : BaseRequestValidator<CustomTokenReque
         IUpdateInstallationCommand updateInstallationCommand,
         IPolicyRequirementQuery policyRequirementQuery,
         IAuthRequestRepository authRequestRepository,
-        IMailService mailService)
+        IMailService mailService,
+        IUserAccountKeysQuery userAccountKeysQuery)
         : base(
             userManager,
             userService,
@@ -65,7 +67,8 @@ public class CustomTokenRequestValidator : BaseRequestValidator<CustomTokenReque
             userDecryptionOptionsBuilder,
             policyRequirementQuery,
             authRequestRepository,
-            mailService)
+            mailService,
+            userAccountKeysQuery)
     {
         _userManager = userManager;
         _updateInstallationCommand = updateInstallationCommand;

src/Identity/IdentityServer/RequestValidators/ResourceOwnerPasswordValidator.cs

@@ -8,6 +8,7 @@ using Bit.Core.AdminConsole.Services;
 using Bit.Core.Auth.Repositories;
 using Bit.Core.Context;
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Settings;
@@ -41,7 +42,8 @@ public class ResourceOwnerPasswordValidator : BaseRequestValidator<ResourceOwner
         ISsoConfigRepository ssoConfigRepository,
         IUserDecryptionOptionsBuilder userDecryptionOptionsBuilder,
         IPolicyRequirementQuery policyRequirementQuery,
-        IMailService mailService)
+        IMailService mailService,
+        IUserAccountKeysQuery userAccountKeysQuery)
         : base(
             userManager,
             userService,
@@ -59,7 +61,8 @@ public class ResourceOwnerPasswordValidator : BaseRequestValidator<ResourceOwner
             userDecryptionOptionsBuilder,
             policyRequirementQuery,
             authRequestRepository,
-            mailService)
+            mailService,
+            userAccountKeysQuery)
     {
         _userManager = userManager;
         _currentContext = currentContext;

src/Identity/IdentityServer/RequestValidators/WebAuthnGrantValidator.cs

@@ -12,6 +12,7 @@ using Bit.Core.Auth.Repositories;
 using Bit.Core.Auth.UserFeatures.WebAuthnLogin;
 using Bit.Core.Context;
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Settings;
@@ -50,7 +51,8 @@ public class WebAuthnGrantValidator : BaseRequestValidator<ExtensionGrantValidat
         IAssertWebAuthnLoginCredentialCommand assertWebAuthnLoginCredentialCommand,
         IPolicyRequirementQuery policyRequirementQuery,
         IAuthRequestRepository authRequestRepository,
-        IMailService mailService)
+        IMailService mailService,
+        IUserAccountKeysQuery userAccountKeysQuery)
         : base(
             userManager,
             userService,
@@ -68,7 +70,8 @@ public class WebAuthnGrantValidator : BaseRequestValidator<ExtensionGrantValidat
             userDecryptionOptionsBuilder,
             policyRequirementQuery,
             authRequestRepository,
-            mailService)
+            mailService,
+            userAccountKeysQuery)
     {
         _assertionOptionsDataProtector = assertionOptionsDataProtector;
         _assertWebAuthnLoginCredentialCommand = assertWebAuthnLoginCredentialCommand;

src/Identity/IdentityServer/UserDecryptionOptionsBuilder.cs

@@ -6,7 +6,7 @@ using Bit.Core.Auth.Utilities;
 using Bit.Core.Context;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
-using Bit.Core.KeyManagement.Models.Response;
+using Bit.Core.KeyManagement.Models.Api.Response;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Utilities;

src/Infrastructure.Dapper/DapperServiceCollectionExtensions.cs

@@ -71,6 +71,7 @@ public static class DapperServiceCollectionExtensions
         services.AddSingleton<ISecurityTaskRepository, SecurityTaskRepository>();
         services.AddSingleton<IUserAsymmetricKeysRepository, UserAsymmetricKeysRepository>();
         services.AddSingleton<IOrganizationInstallationRepository, OrganizationInstallationRepository>();
+        services.AddSingleton<IUserSignatureKeyPairRepository, UserSignatureKeyPairRepository>();
         services.AddSingleton<IOrganizationReportRepository, OrganizationReportRepository>();
         services.AddSingleton<IOrganizationApplicationRepository, OrganizationApplicationRepository>();
         services.AddSingleton<IOrganizationMemberBaseDetailRepository, OrganizationMemberBaseDetailRepository>();

src/Infrastructure.Dapper/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

@@ -0,0 +1,79 @@
+using System.Data;
+using Bit.Core.KeyManagement.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Repositories;
+using Bit.Core.KeyManagement.UserKey;
+using Bit.Core.Settings;
+using Bit.Core.Utilities;
+using Bit.Infrastructure.Dapper.Repositories;
+using Dapper;
+using Microsoft.Data.SqlClient;
+
+namespace Bit.Infrastructure.Dapper.KeyManagement.Repositories;
+
+public class UserSignatureKeyPairRepository : Repository<UserSignatureKeyPair, Guid>, IUserSignatureKeyPairRepository
+{
+    public UserSignatureKeyPairRepository(GlobalSettings globalSettings)
+        : this(globalSettings.SqlServer.ConnectionString, globalSettings.SqlServer.ReadOnlyConnectionString)
+    {
+    }
+
+    public UserSignatureKeyPairRepository(string connectionString, string readOnlyConnectionString) : base(
+        connectionString, readOnlyConnectionString)
+    {
+    }
+
+    public async Task<SignatureKeyPairData?> GetByUserIdAsync(Guid userId)
+    {
+        using (var connection = new SqlConnection(ConnectionString))
+        {
+            return (await connection.QuerySingleOrDefaultAsync<UserSignatureKeyPair>(
+                "[dbo].[UserSignatureKeyPair_ReadByUserId]",
+                new
+                {
+                    UserId = userId
+                },
+                commandType: CommandType.StoredProcedure))?.ToSignatureKeyPairData();
+        }
+    }
+
+    public UpdateEncryptedDataForKeyRotation SetUserSignatureKeyPair(Guid userId, SignatureKeyPairData signingKeys)
+    {
+        return async (SqlConnection connection, SqlTransaction transaction) =>
+        {
+            await connection.QueryAsync(
+                "[dbo].[UserSignatureKeyPair_SetForRotation]",
+                new
+                {
+                    Id = CoreHelpers.GenerateComb(),
+                    UserId = userId,
+                    SignatureAlgorithm = (byte)signingKeys.SignatureAlgorithm,
+                    SigningKey = signingKeys.WrappedSigningKey,
+                    VerifyingKey = signingKeys.VerifyingKey,
+                    CreationDate = DateTime.UtcNow,
+                    RevisionDate = DateTime.UtcNow
+                },
+                commandType: CommandType.StoredProcedure,
+                transaction: transaction);
+        };
+    }
+
+    public UpdateEncryptedDataForKeyRotation UpdateForKeyRotation(Guid grantorId, SignatureKeyPairData signingKeys)
+    {
+        return async (SqlConnection connection, SqlTransaction transaction) =>
+        {
+            await connection.QueryAsync(
+                "[dbo].[UserSignatureKeyPair_UpdateForRotation]",
+                new
+                {
+                    UserId = grantorId,
+                    SignatureAlgorithm = (byte)signingKeys.SignatureAlgorithm,
+                    SigningKey = signingKeys.WrappedSigningKey,
+                    VerifyingKey = signingKeys.VerifyingKey,
+                    RevisionDate = DateTime.UtcNow
+                },
+                commandType: CommandType.StoredProcedure,
+                transaction: transaction);
+        };
+    }
+}

src/Infrastructure.EntityFramework/EntityFrameworkServiceCollectionExtensions.cs

@@ -108,6 +108,7 @@ public static class EntityFrameworkServiceCollectionExtensions
         services.AddSingleton<IPasswordHealthReportApplicationRepository, PasswordHealthReportApplicationRepository>();
         services.AddSingleton<ISecurityTaskRepository, SecurityTaskRepository>();
         services.AddSingleton<IUserAsymmetricKeysRepository, UserAsymmetricKeysRepository>();
+        services.AddSingleton<IUserSignatureKeyPairRepository, UserSignatureKeyPairRepository>();
         services.AddSingleton<IOrganizationInstallationRepository, OrganizationInstallationRepository>();
         services.AddSingleton<IOrganizationReportRepository, OrganizationReportRepository>();
         services.AddSingleton<IOrganizationApplicationRepository, OrganizationApplicationRepository>();

src/Infrastructure.EntityFramework/KeyManagement/Configurations/UserSignatureKeyPairEntityTypeConfiguration.cs

@@ -0,0 +1,22 @@
+using Bit.Infrastructure.EntityFramework.Models;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Metadata.Builders;
+
+namespace Bit.Infrastructure.EntityFramework.Configurations;
+
+public class UserSignatureKeyPairEntityTypeConfiguration : IEntityTypeConfiguration<UserSignatureKeyPair>
+{
+    public void Configure(EntityTypeBuilder<UserSignatureKeyPair> builder)
+    {
+        builder
+            .Property(s => s.Id)
+            .ValueGeneratedNever();
+
+        builder
+            .HasIndex(s => s.UserId)
+            .IsUnique()
+            .IsClustered(false);
+
+        builder.ToTable(nameof(UserSignatureKeyPair));
+    }
+}

src/Infrastructure.EntityFramework/KeyManagement/Models/UserSignatureKeyPair.cs

@@ -0,0 +1,19 @@
+// FIXME: Update this file to be null safe and then delete the line below
+#nullable disable
+
+using AutoMapper;
+
+namespace Bit.Infrastructure.EntityFramework.Models;
+
+public class UserSignatureKeyPair : Core.KeyManagement.Entities.UserSignatureKeyPair
+{
+    public virtual User User { get; set; }
+}
+
+public class UserSignatureKeyPairMapperProfile : Profile
+{
+    public UserSignatureKeyPairMapperProfile()
+    {
+        CreateMap<Core.KeyManagement.Entities.UserSignatureKeyPair, UserSignatureKeyPair>().ReverseMap();
+    }
+}

src/Infrastructure.EntityFramework/KeyManagement/Repositories/UserSignatureKeyPairRepository.cs

@@ -0,0 +1,66 @@
+
+using AutoMapper;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Repositories;
+using Bit.Core.KeyManagement.UserKey;
+using Bit.Core.Utilities;
+using Bit.Infrastructure.EntityFramework.Repositories;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.Extensions.DependencyInjection;
+
+namespace Bit.Infrastructure.EntityFramework.KeyManagement.Repositories;
+
+public class UserSignatureKeyPairRepository(IServiceScopeFactory serviceScopeFactory, IMapper mapper) : Repository<Core.KeyManagement.Entities.UserSignatureKeyPair, Models.UserSignatureKeyPair, Guid>(serviceScopeFactory, mapper, context => context.UserSignatureKeyPairs), IUserSignatureKeyPairRepository
+{
+    public async Task<SignatureKeyPairData?> GetByUserIdAsync(Guid userId)
+    {
+        await using var scope = ServiceScopeFactory.CreateAsyncScope();
+        var dbContext = GetDatabaseContext(scope);
+        var signingKeys = await dbContext.UserSignatureKeyPairs.FirstOrDefaultAsync(x => x.UserId == userId);
+        if (signingKeys == null)
+        {
+            return null;
+        }
+
+        return signingKeys.ToSignatureKeyPairData();
+    }
+
+    public UpdateEncryptedDataForKeyRotation SetUserSignatureKeyPair(Guid userId, SignatureKeyPairData signingKeys)
+    {
+        return async (_, _) =>
+        {
+            await using var scope = ServiceScopeFactory.CreateAsyncScope();
+            var dbContext = GetDatabaseContext(scope);
+            var entity = new Models.UserSignatureKeyPair
+            {
+                Id = CoreHelpers.GenerateComb(),
+                UserId = userId,
+                SignatureAlgorithm = signingKeys.SignatureAlgorithm,
+                SigningKey = signingKeys.WrappedSigningKey,
+                VerifyingKey = signingKeys.VerifyingKey,
+                CreationDate = DateTime.UtcNow,
+                RevisionDate = DateTime.UtcNow,
+            };
+            await dbContext.UserSignatureKeyPairs.AddAsync(entity);
+            await dbContext.SaveChangesAsync();
+        };
+    }
+
+    public UpdateEncryptedDataForKeyRotation UpdateForKeyRotation(Guid grantorId, SignatureKeyPairData signingKeys)
+    {
+        return async (_, _) =>
+        {
+            await using var scope = ServiceScopeFactory.CreateAsyncScope();
+            var dbContext = GetDatabaseContext(scope);
+            var entity = await dbContext.UserSignatureKeyPairs.FirstOrDefaultAsync(x => x.UserId == grantorId);
+            if (entity != null)
+            {
+                entity.SignatureAlgorithm = signingKeys.SignatureAlgorithm;
+                entity.SigningKey = signingKeys.WrappedSigningKey;
+                entity.VerifyingKey = signingKeys.VerifyingKey;
+                entity.RevisionDate = DateTime.UtcNow;
+                await dbContext.SaveChangesAsync();
+            }
+        };
+    }
+}

src/Infrastructure.EntityFramework/Repositories/DatabaseContext.cs

@@ -74,6 +74,7 @@ public class DatabaseContext : DbContext
     public DbSet<TaxRate> TaxRates { get; set; }
     public DbSet<Transaction> Transactions { get; set; }
     public DbSet<User> Users { get; set; }
+    public DbSet<UserSignatureKeyPair> UserSignatureKeyPairs { get; set; }
     public DbSet<AuthRequest> AuthRequests { get; set; }
     public DbSet<OrganizationDomain> OrganizationDomains { get; set; }
     public DbSet<WebAuthnCredential> WebAuthnCredentials { get; set; }

src/Sql/dbo/KeyManagement/Stored Procedures/UserSignatureKeyPair_ReadByUserId.sql

@@ -0,0 +1,13 @@
+CREATE PROCEDURE [dbo].[UserSignatureKeyPair_ReadByUserId]
+    @UserId UNIQUEIDENTIFIER
+AS
+BEGIN
+    SET NOCOUNT ON;
+
+    SELECT
+        *
+    FROM
+        [dbo].[UserSignatureKeyPairView]
+    WHERE
+        [UserId] = @UserId;
+END

src/Sql/dbo/KeyManagement/Stored Procedures/UserSignatureKeyPair_SetForRotation.sql

@@ -0,0 +1,33 @@
+CREATE PROCEDURE [dbo].[UserSignatureKeyPair_SetForRotation]
+    @Id UNIQUEIDENTIFIER,
+    @UserId UNIQUEIDENTIFIER,
+    @SignatureAlgorithm TINYINT,
+    @SigningKey VARCHAR(MAX),
+    @VerifyingKey VARCHAR(MAX),
+    @CreationDate DATETIME2(7),
+    @RevisionDate DATETIME2(7)
+AS
+BEGIN
+    SET NOCOUNT ON;
+
+    INSERT INTO [dbo].[UserSignatureKeyPair] 
+    (
+        [Id], 
+        [UserId], 
+        [SignatureAlgorithm], 
+        [SigningKey], 
+        [VerifyingKey], 
+        [CreationDate], 
+        [RevisionDate]
+    )
+    VALUES 
+    (
+        @Id, 
+        @UserId, 
+        @SignatureAlgorithm, 
+        @SigningKey, 
+        @VerifyingKey, 
+        @CreationDate, 
+        @RevisionDate
+    )
+END

src/Sql/dbo/KeyManagement/Stored Procedures/UserSignatureKeyPair_UpdateForRotation.sql

@@ -0,0 +1,19 @@
+CREATE PROCEDURE [dbo].[UserSignatureKeyPair_UpdateForRotation]
+    @UserId UNIQUEIDENTIFIER,
+    @SignatureAlgorithm TINYINT,
+    @SigningKey VARCHAR(MAX),
+    @VerifyingKey VARCHAR(MAX),
+    @RevisionDate DATETIME2(7)
+AS
+BEGIN
+    SET NOCOUNT ON;
+    UPDATE  
+        [dbo].[UserSignatureKeyPair]  
+    SET  
+        [SignatureAlgorithm] = @SignatureAlgorithm,  
+        [SigningKey] = @SigningKey,  
+        [VerifyingKey] = @VerifyingKey,  
+        [RevisionDate] = @RevisionDate  
+    WHERE  
+        [UserId] = @UserId;
+END

src/Sql/dbo/KeyManagement/Tables/UserSignatureKeyPair.sql

@@ -0,0 +1,16 @@
+CREATE TABLE [dbo].[UserSignatureKeyPair] (
+    [Id]                        UNIQUEIDENTIFIER NOT NULL,
+    [UserId]                    UNIQUEIDENTIFIER NOT NULL,
+    [SignatureAlgorithm]        TINYINT NOT NULL,
+    [SigningKey]                VARCHAR(MAX) NOT NULL,
+    [VerifyingKey]              VARCHAR(MAX) NOT NULL,
+    [CreationDate]              DATETIME2 (7) NOT NULL,
+    [RevisionDate]              DATETIME2 (7) NOT NULL,
+    CONSTRAINT [PK_UserSignatureKeyPair] PRIMARY KEY CLUSTERED ([Id] ASC),
+    CONSTRAINT [FK_UserSignatureKeyPair_User] FOREIGN KEY ([UserId]) REFERENCES [dbo].[User] ([Id]) ON DELETE CASCADE
+);
+GO
+
+CREATE UNIQUE NONCLUSTERED INDEX [IX_UserSignatureKeyPair_UserId]
+    ON [dbo].[UserSignatureKeyPair]([UserId] ASC);
+GO

src/Sql/dbo/KeyManagement/Views/UserSignatureKeyPairView.sql

@@ -0,0 +1,6 @@
+CREATE VIEW [dbo].[UserSignatureKeyPairView]
+AS
+SELECT
+    *
+FROM
+    [dbo].[UserSignatureKeyPair]

src/Sql/dbo/Stored Procedures/User_Create.sql

@@ -41,7 +41,10 @@
     @LastKdfChangeDate DATETIME2(7) = NULL,
     @LastKeyRotationDate DATETIME2(7) = NULL,
     @LastEmailChangeDate DATETIME2(7) = NULL,
-    @VerifyDevices BIT = 1
+    @VerifyDevices BIT = 1,
+    @SecurityState VARCHAR(MAX) = NULL,
+    @SecurityVersion INT = NULL,
+    @SignedPublicKey VARCHAR(MAX) = NULL
 AS
 BEGIN
     SET NOCOUNT ON
@@ -90,7 +93,10 @@ BEGIN
         [LastKdfChangeDate],
         [LastKeyRotationDate],
         [LastEmailChangeDate],
-        [VerifyDevices]
+        [VerifyDevices],
+        [SecurityState],
+        [SecurityVersion],
+        [SignedPublicKey]
     )
     VALUES
     (
@@ -136,6 +142,9 @@ BEGIN
         @LastKdfChangeDate,
         @LastKeyRotationDate,
         @LastEmailChangeDate,
-        @VerifyDevices
+        @VerifyDevices,
+        @SecurityState,
+        @SecurityVersion,
+        @SignedPublicKey
     )
 END

src/Sql/dbo/Stored Procedures/User_Update.sql

@@ -41,7 +41,10 @@
     @LastKdfChangeDate DATETIME2(7) = NULL,
     @LastKeyRotationDate DATETIME2(7) = NULL,
     @LastEmailChangeDate DATETIME2(7) = NULL,
-    @VerifyDevices BIT = 1
+    @VerifyDevices BIT = 1,
+    @SecurityState VARCHAR(MAX) = NULL,
+    @SecurityVersion INT = NULL,
+    @SignedPublicKey VARCHAR(MAX) = NULL
 AS
 BEGIN
     SET NOCOUNT ON
@@ -90,7 +93,10 @@ BEGIN
         [LastKdfChangeDate] = @LastKdfChangeDate,
         [LastKeyRotationDate] = @LastKeyRotationDate,
         [LastEmailChangeDate] = @LastEmailChangeDate,
-        [VerifyDevices] = @VerifyDevices
+        [VerifyDevices] = @VerifyDevices,
+        [SecurityState] = @SecurityState,
+        [SecurityVersion] = @SecurityVersion,
+        [SignedPublicKey] = @SignedPublicKey
     WHERE
         [Id] = @Id
 END

src/Sql/dbo/Tables/User.sql

@@ -42,6 +42,9 @@
     [LastKeyRotationDate]              DATETIME2 (7)    NULL,
     [LastEmailChangeDate]              DATETIME2 (7)    NULL,
     [VerifyDevices]                    BIT              DEFAULT ((1)) NOT NULL,
+    [SecurityState]                    VARCHAR (MAX)   NULL,
+    [SecurityVersion]                  INT              NULL,
+    [SignedPublicKey]                  VARCHAR (MAX)   NULL,
     CONSTRAINT [PK_User] PRIMARY KEY CLUSTERED ([Id] ASC)
 );
 

test/Api.IntegrationTest/KeyManagement/Controllers/AccountsKeyManagementControllerTests.cs

@@ -12,6 +12,10 @@ using Bit.Core.Auth.Models.Api.Request.Accounts;
 using Bit.Core.Billing.Enums;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
+using Bit.Core.KeyManagement.Entities;
+using Bit.Core.KeyManagement.Enums;
+using Bit.Core.KeyManagement.Models.Api.Request;
+using Bit.Core.KeyManagement.Repositories;
 using Bit.Core.Repositories;
 using Bit.Core.Vault.Enums;
 using Bit.Test.Common.AutoFixture.Attributes;
@@ -24,6 +28,7 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
 {
     private static readonly string _mockEncryptedString =
         "2.AOs41Hd8OQiCPXjyJKCiDA==|O6OHgt2U2hJGBSNGnimJmg==|iD33s8B69C8JhYYhSa4V1tArjvLr8eEaGqOV7BRo5Jk=";
+    private static readonly string _mockEncryptedType7String = "7.AOs41Hd8OQiCPXjyJKCiDA==";
 
     private readonly HttpClient _client;
     private readonly IEmergencyAccessRepository _emergencyAccessRepository;
@@ -34,6 +39,7 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
     private readonly IDeviceRepository _deviceRepository;
     private readonly IPasswordHasher<User> _passwordHasher;
     private readonly IOrganizationRepository _organizationRepository;
+    private readonly IUserSignatureKeyPairRepository _userSignatureKeyPairRepository;
     private string _ownerEmail = null!;
 
     public AccountsKeyManagementControllerTests(ApiApplicationFactory factory)
@@ -49,6 +55,7 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
         _organizationUserRepository = _factory.GetService<IOrganizationUserRepository>();
         _passwordHasher = _factory.GetService<IPasswordHasher<User>>();
         _organizationRepository = _factory.GetService<IOrganizationRepository>();
+        _userSignatureKeyPairRepository = _factory.GetService<IUserSignatureKeyPairRepository>();
     }
 
     public async Task InitializeAsync()
@@ -200,6 +207,7 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
         var password = _passwordHasher.HashPassword(user, "newMasterPassword");
         user.MasterPassword = password;
         user.PublicKey = "publicKey";
+        user.PrivateKey = _mockEncryptedString;
         await _userRepository.ReplaceAsync(user);
 
         request.AccountUnlockData.MasterPasswordUnlockData.KdfType = user.Kdf;
@@ -209,6 +217,8 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
         request.AccountUnlockData.MasterPasswordUnlockData.Email = user.Email;
         request.AccountKeys.AccountPublicKey = "publicKey";
         request.AccountKeys.UserKeyEncryptedAccountPrivateKey = _mockEncryptedString;
+        request.AccountKeys.PublicKeyEncryptionKeyPair = null;
+        request.AccountKeys.SignatureKeyPair = null;
 
         request.OldMasterKeyAuthenticationHash = "newMasterPassword";
 
@@ -354,4 +364,196 @@ public class AccountsKeyManagementControllerTests : IClassFixture<ApiApplication
         Assert.Equal(DateTime.UtcNow, user.RevisionDate, TimeSpan.FromMinutes(1));
         Assert.Equal(DateTime.UtcNow, user.AccountRevisionDate, TimeSpan.FromMinutes(1));
     }
+
+    [Theory]
+    [BitAutoData]
+    public async Task RotateV2UserAccountKeysAsync_Success(RotateUserAccountKeysAndDataRequestModel request)
+    {
+        await _loginHelper.LoginAsync(_ownerEmail);
+        var user = await _userRepository.GetByEmailAsync(_ownerEmail);
+        if (user == null)
+        {
+            throw new InvalidOperationException("User not found.");
+        }
+
+        var password = _passwordHasher.HashPassword(user, "newMasterPassword");
+        user.MasterPassword = password;
+        user.PublicKey = "publicKey";
+        user.PrivateKey = _mockEncryptedType7String;
+
+        await _userRepository.ReplaceAsync(user);
+        await _userSignatureKeyPairRepository.CreateAsync(new UserSignatureKeyPair
+        {
+            UserId = user.Id,
+            SignatureAlgorithm = SignatureAlgorithm.Ed25519,
+            SigningKey = _mockEncryptedType7String,
+            VerifyingKey = "verifyingKey",
+        });
+
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfType = user.Kdf;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfIterations = user.KdfIterations;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfMemory = user.KdfMemory;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfParallelism = user.KdfParallelism;
+        request.AccountUnlockData.MasterPasswordUnlockData.Email = user.Email;
+        request.AccountKeys.AccountPublicKey = "publicKey";
+        request.AccountKeys.UserKeyEncryptedAccountPrivateKey = _mockEncryptedType7String;
+        request.AccountKeys.PublicKeyEncryptionKeyPair = new PublicKeyEncryptionKeyPairRequestModel
+        {
+            PublicKey = "publicKey",
+            WrappedPrivateKey = _mockEncryptedType7String,
+            SignedPublicKey = "signedPublicKey",
+        };
+        request.AccountKeys.SignatureKeyPair = new SignatureKeyPairRequestModel
+        {
+            SignatureAlgorithm = "ed25519",
+            WrappedSigningKey = _mockEncryptedType7String,
+            VerifyingKey = "verifyingKey",
+        };
+
+        request.OldMasterKeyAuthenticationHash = "newMasterPassword";
+
+        request.AccountData.Ciphers =
+        [
+            new CipherWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Type = CipherType.Login,
+                Name = _mockEncryptedString,
+                Login = new CipherLoginModel
+                {
+                    Username = _mockEncryptedString,
+                    Password = _mockEncryptedString,
+                },
+            },
+        ];
+        request.AccountData.Folders = [
+            new FolderWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Name = _mockEncryptedString,
+            },
+        ];
+        request.AccountData.Sends = [
+            new SendWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Name = _mockEncryptedString,
+                Key = _mockEncryptedString,
+                Disabled = false,
+                DeletionDate = DateTime.UtcNow.AddDays(1),
+            },
+        ];
+        request.AccountUnlockData.MasterPasswordUnlockData.MasterKeyEncryptedUserKey = _mockEncryptedString;
+        request.AccountUnlockData.PasskeyUnlockData = [];
+        request.AccountUnlockData.DeviceKeyUnlockData = [];
+        request.AccountUnlockData.EmergencyAccessUnlockData = [];
+        request.AccountUnlockData.OrganizationAccountRecoveryUnlockData = [];
+
+        var response = await _client.PostAsJsonAsync("/accounts/key-management/rotate-user-account-keys", request);
+        var responseMessage = await response.Content.ReadAsStringAsync();
+        response.EnsureSuccessStatusCode();
+
+        var userNewState = await _userRepository.GetByEmailAsync(_ownerEmail);
+        Assert.NotNull(userNewState);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.Email, userNewState.Email);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfType, userNewState.Kdf);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfIterations, userNewState.KdfIterations);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfMemory, userNewState.KdfMemory);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfParallelism, userNewState.KdfParallelism);
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task RotateUpgradeToV2UserAccountKeysAsync_Success(RotateUserAccountKeysAndDataRequestModel request)
+    {
+        await _loginHelper.LoginAsync(_ownerEmail);
+        var user = await _userRepository.GetByEmailAsync(_ownerEmail);
+        if (user == null)
+        {
+            throw new InvalidOperationException("User not found.");
+        }
+
+        var password = _passwordHasher.HashPassword(user, "newMasterPassword");
+        user.MasterPassword = password;
+        user.PublicKey = "publicKey";
+        user.PrivateKey = _mockEncryptedString;
+
+        await _userRepository.ReplaceAsync(user);
+
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfType = user.Kdf;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfIterations = user.KdfIterations;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfMemory = user.KdfMemory;
+        request.AccountUnlockData.MasterPasswordUnlockData.KdfParallelism = user.KdfParallelism;
+        request.AccountUnlockData.MasterPasswordUnlockData.Email = user.Email;
+        request.AccountKeys.AccountPublicKey = "publicKey";
+        request.AccountKeys.UserKeyEncryptedAccountPrivateKey = _mockEncryptedType7String;
+        request.AccountKeys.PublicKeyEncryptionKeyPair = new PublicKeyEncryptionKeyPairRequestModel
+        {
+            PublicKey = "publicKey",
+            WrappedPrivateKey = _mockEncryptedType7String,
+            SignedPublicKey = "signedPublicKey",
+        };
+        request.AccountKeys.SignatureKeyPair = new SignatureKeyPairRequestModel
+        {
+            SignatureAlgorithm = "ed25519",
+            WrappedSigningKey = _mockEncryptedType7String,
+            VerifyingKey = "verifyingKey",
+        };
+        request.AccountKeys.SecurityState = new SecurityStateModel
+        {
+            SecurityVersion = 2,
+            SecurityState = "v2",
+        };
+
+        request.OldMasterKeyAuthenticationHash = "newMasterPassword";
+
+        request.AccountData.Ciphers =
+        [
+            new CipherWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Type = CipherType.Login,
+                Name = _mockEncryptedString,
+                Login = new CipherLoginModel
+                {
+                    Username = _mockEncryptedString,
+                    Password = _mockEncryptedString,
+                },
+            },
+        ];
+        request.AccountData.Folders = [
+            new FolderWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Name = _mockEncryptedString,
+            },
+        ];
+        request.AccountData.Sends = [
+            new SendWithIdRequestModel
+            {
+                Id = Guid.NewGuid(),
+                Name = _mockEncryptedString,
+                Key = _mockEncryptedString,
+                Disabled = false,
+                DeletionDate = DateTime.UtcNow.AddDays(1),
+            },
+        ];
+        request.AccountUnlockData.MasterPasswordUnlockData.MasterKeyEncryptedUserKey = _mockEncryptedString;
+        request.AccountUnlockData.PasskeyUnlockData = [];
+        request.AccountUnlockData.DeviceKeyUnlockData = [];
+        request.AccountUnlockData.EmergencyAccessUnlockData = [];
+        request.AccountUnlockData.OrganizationAccountRecoveryUnlockData = [];
+
+        var response = await _client.PostAsJsonAsync("/accounts/key-management/rotate-user-account-keys", request);
+        var responseMessage = await response.Content.ReadAsStringAsync();
+        response.EnsureSuccessStatusCode();
+
+        var userNewState = await _userRepository.GetByEmailAsync(_ownerEmail);
+        Assert.NotNull(userNewState);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.Email, userNewState.Email);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfType, userNewState.Kdf);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfIterations, userNewState.KdfIterations);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfMemory, userNewState.KdfMemory);
+        Assert.Equal(request.AccountUnlockData.MasterPasswordUnlockData.KdfParallelism, userNewState.KdfParallelism);
+    }
 }

test/Api.Test/Auth/Controllers/AccountsControllerTests.cs

@@ -11,6 +11,7 @@ using Bit.Core.Auth.UserFeatures.UserMasterPassword.Interfaces;
 using Bit.Core.Entities;
 using Bit.Core.Exceptions;
 using Bit.Core.KeyManagement.Kdf;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Test.Common.AutoFixture.Attributes;
@@ -33,10 +34,10 @@ public class AccountsControllerTests : IDisposable
     private readonly ITwoFactorIsEnabledQuery _twoFactorIsEnabledQuery;
     private readonly ITdeOffboardingPasswordCommand _tdeOffboardingPasswordCommand;
     private readonly IFeatureService _featureService;
+    private readonly IUserAccountKeysQuery _userAccountKeysQuery;
     private readonly ITwoFactorEmailService _twoFactorEmailService;
     private readonly IChangeKdfCommand _changeKdfCommand;
 
-
     public AccountsControllerTests()
     {
         _userService = Substitute.For<IUserService>();
@@ -48,6 +49,7 @@ public class AccountsControllerTests : IDisposable
         _twoFactorIsEnabledQuery = Substitute.For<ITwoFactorIsEnabledQuery>();
         _tdeOffboardingPasswordCommand = Substitute.For<ITdeOffboardingPasswordCommand>();
         _featureService = Substitute.For<IFeatureService>();
+        _userAccountKeysQuery = Substitute.For<IUserAccountKeysQuery>();
         _twoFactorEmailService = Substitute.For<ITwoFactorEmailService>();
         _changeKdfCommand = Substitute.For<IChangeKdfCommand>();
 
@@ -61,6 +63,7 @@ public class AccountsControllerTests : IDisposable
             _tdeOffboardingPasswordCommand,
             _twoFactorIsEnabledQuery,
             _featureService,
+            _userAccountKeysQuery,
             _twoFactorEmailService,
             _changeKdfCommand
         );

test/Api.Test/KeyManagement/Controllers/AccountsKeyManagementControllerTests.cs

@@ -110,6 +110,7 @@ public class AccountsKeyManagementControllerTests
     public async Task RotateUserAccountKeysSuccess(SutProvider<AccountsKeyManagementController> sutProvider,
         RotateUserAccountKeysAndDataRequestModel data, User user)
     {
+        data.AccountKeys.SignatureKeyPair = null;
         sutProvider.GetDependency<IUserService>().GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
         sutProvider.GetDependency<IRotateUserAccountKeysCommand>().RotateUserAccountKeysAsync(Arg.Any<User>(), Arg.Any<RotateUserAccountKeysData>())
             .Returns(IdentityResult.Success);
@@ -142,8 +143,60 @@ public class AccountsKeyManagementControllerTests
                 && d.MasterPasswordUnlockData.MasterKeyAuthenticationHash == data.AccountUnlockData.MasterPasswordUnlockData.MasterKeyAuthenticationHash
                 && d.MasterPasswordUnlockData.MasterKeyEncryptedUserKey == data.AccountUnlockData.MasterPasswordUnlockData.MasterKeyEncryptedUserKey
 
-                && d.AccountPublicKey == data.AccountKeys.AccountPublicKey
+                && d.AccountKeys!.PublicKeyEncryptionKeyPairData.WrappedPrivateKey == data.AccountKeys.PublicKeyEncryptionKeyPair!.WrappedPrivateKey
-                && d.UserKeyEncryptedAccountPrivateKey == data.AccountKeys.UserKeyEncryptedAccountPrivateKey
+                && d.AccountKeys!.PublicKeyEncryptionKeyPairData.PublicKey == data.AccountKeys.PublicKeyEncryptionKeyPair!.PublicKey
+            ));
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task RotateUserAccountKeys_UserCryptoV2_Success_Async(SutProvider<AccountsKeyManagementController> sutProvider,
+    RotateUserAccountKeysAndDataRequestModel data, User user)
+    {
+        data.AccountKeys.SignatureKeyPair = new SignatureKeyPairRequestModel
+        {
+            SignatureAlgorithm = "ed25519",
+            WrappedSigningKey = "wrappedSigningKey",
+            VerifyingKey = "verifyingKey"
+        };
+        sutProvider.GetDependency<IUserService>().GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
+        sutProvider.GetDependency<IRotateUserAccountKeysCommand>().RotateUserAccountKeysAsync(Arg.Any<User>(), Arg.Any<RotateUserAccountKeysData>())
+            .Returns(IdentityResult.Success);
+        await sutProvider.Sut.RotateUserAccountKeysAsync(data);
+
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<EmergencyAccessWithIdRequestModel>, IEnumerable<EmergencyAccess>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountUnlockData.EmergencyAccessUnlockData));
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<ResetPasswordWithOrgIdRequestModel>, IReadOnlyList<OrganizationUser>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountUnlockData.OrganizationAccountRecoveryUnlockData));
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<WebAuthnLoginRotateKeyRequestModel>, IEnumerable<WebAuthnLoginRotateKeyData>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountUnlockData.PasskeyUnlockData));
+
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<CipherWithIdRequestModel>, IEnumerable<Cipher>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountData.Ciphers));
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<FolderWithIdRequestModel>, IEnumerable<Folder>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountData.Folders));
+        await sutProvider.GetDependency<IRotationValidator<IEnumerable<SendWithIdRequestModel>, IReadOnlyList<Send>>>().Received(1)
+            .ValidateAsync(Arg.Any<User>(), Arg.Is(data.AccountData.Sends));
+
+        await sutProvider.GetDependency<IRotateUserAccountKeysCommand>().Received(1)
+            .RotateUserAccountKeysAsync(Arg.Is(user), Arg.Is<RotateUserAccountKeysData>(d =>
+                d.OldMasterKeyAuthenticationHash == data.OldMasterKeyAuthenticationHash
+
+                && d.MasterPasswordUnlockData.KdfType == data.AccountUnlockData.MasterPasswordUnlockData.KdfType
+                && d.MasterPasswordUnlockData.KdfIterations == data.AccountUnlockData.MasterPasswordUnlockData.KdfIterations
+                && d.MasterPasswordUnlockData.KdfMemory == data.AccountUnlockData.MasterPasswordUnlockData.KdfMemory
+                && d.MasterPasswordUnlockData.KdfParallelism == data.AccountUnlockData.MasterPasswordUnlockData.KdfParallelism
+                && d.MasterPasswordUnlockData.Email == data.AccountUnlockData.MasterPasswordUnlockData.Email
+
+                && d.MasterPasswordUnlockData.MasterKeyAuthenticationHash == data.AccountUnlockData.MasterPasswordUnlockData.MasterKeyAuthenticationHash
+                && d.MasterPasswordUnlockData.MasterKeyEncryptedUserKey == data.AccountUnlockData.MasterPasswordUnlockData.MasterKeyEncryptedUserKey
+
+                && d.AccountKeys!.PublicKeyEncryptionKeyPairData.WrappedPrivateKey == data.AccountKeys.PublicKeyEncryptionKeyPair!.WrappedPrivateKey
+                && d.AccountKeys!.PublicKeyEncryptionKeyPairData.PublicKey == data.AccountKeys.PublicKeyEncryptionKeyPair!.PublicKey
+                && d.AccountKeys!.PublicKeyEncryptionKeyPairData.SignedPublicKey == data.AccountKeys.PublicKeyEncryptionKeyPair!.SignedPublicKey
+                && d.AccountKeys!.SignatureKeyPairData!.SignatureAlgorithm == Core.KeyManagement.Enums.SignatureAlgorithm.Ed25519
+                && d.AccountKeys!.SignatureKeyPairData.WrappedSigningKey == data.AccountKeys.SignatureKeyPair!.WrappedSigningKey
+                && d.AccountKeys!.SignatureKeyPairData.VerifyingKey == data.AccountKeys.SignatureKeyPair!.VerifyingKey
             ));
     }
 
@@ -153,6 +206,7 @@ public class AccountsKeyManagementControllerTests
     public async Task RotateUserKeyNoUser_Throws(SutProvider<AccountsKeyManagementController> sutProvider,
         RotateUserAccountKeysAndDataRequestModel data)
     {
+        data.AccountKeys.SignatureKeyPair = null;
         User? user = null;
         sutProvider.GetDependency<IUserService>().GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
         sutProvider.GetDependency<IRotateUserAccountKeysCommand>().RotateUserAccountKeysAsync(Arg.Any<User>(), Arg.Any<RotateUserAccountKeysData>())
@@ -165,6 +219,7 @@ public class AccountsKeyManagementControllerTests
     public async Task RotateUserKeyWrongData_Throws(SutProvider<AccountsKeyManagementController> sutProvider,
         RotateUserAccountKeysAndDataRequestModel data, User user, IdentityErrorDescriber _identityErrorDescriber)
     {
+        data.AccountKeys.SignatureKeyPair = null;
         sutProvider.GetDependency<IUserService>().GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).Returns(user);
         sutProvider.GetDependency<IRotateUserAccountKeysCommand>().RotateUserAccountKeysAsync(Arg.Any<User>(), Arg.Any<RotateUserAccountKeysData>())
             .Returns(IdentityResult.Failed(_identityErrorDescriber.PasswordMismatch()));

test/Api.Test/KeyManagement/Controllers/UsersControllerTests.cs

@@ -0,0 +1,112 @@
+#nullable enable
+using Bit.Api.KeyManagement.Controllers;
+using Bit.Core.Entities;
+using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Enums;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries.Interfaces;
+using Bit.Core.Repositories;
+using Bit.Test.Common.AutoFixture;
+using Bit.Test.Common.AutoFixture.Attributes;
+using NSubstitute;
+using NSubstitute.ReturnsExtensions;
+using Xunit;
+
+namespace Bit.Api.Test.KeyManagement.Controllers;
+
+[ControllerCustomize(typeof(UsersController))]
+[SutProviderCustomize]
+[JsonDocumentCustomize]
+public class UsersControllerTests
+{
+    [Theory]
+    [BitAutoData]
+    public async Task GetPublicKey_NotFound_ThrowsNotFoundException(
+        SutProvider<UsersController> sutProvider)
+    {
+        sutProvider.GetDependency<IUserRepository>().GetPublicKeyAsync(Arg.Any<Guid>()).ReturnsNull();
+        await Assert.ThrowsAsync<NotFoundException>(() => sutProvider.Sut.GetPublicKeyAsync(new Guid()));
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task GetPublicKey_ReturnsUserKeyResponseModel(
+        SutProvider<UsersController> sutProvider,
+        Guid userId)
+    {
+        var publicKey = "publicKey";
+        sutProvider.GetDependency<IUserRepository>().GetPublicKeyAsync(userId).Returns(publicKey);
+
+        var result = await sutProvider.Sut.GetPublicKeyAsync(userId);
+        Assert.NotNull(result);
+        Assert.Equal(userId, result.UserId);
+        Assert.Equal(publicKey, result.PublicKey);
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task GetAccountKeys_UserNotFound_ThrowsNotFoundException(
+        SutProvider<UsersController> sutProvider)
+    {
+        sutProvider.GetDependency<IUserRepository>().GetByIdAsync(Arg.Any<Guid>()).ReturnsNull();
+        await Assert.ThrowsAsync<NotFoundException>(() => sutProvider.Sut.GetAccountKeysAsync(new Guid()));
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task GetAccountKeys_ReturnsPublicUserKeysResponseModel(
+        SutProvider<UsersController> sutProvider,
+        Guid userId)
+    {
+        var user = new User
+        {
+            Id = userId,
+            PublicKey = "publicKey",
+            SignedPublicKey = "signedPublicKey",
+        };
+
+        sutProvider.GetDependency<IUserRepository>().GetByIdAsync(userId).Returns(user);
+        sutProvider.GetDependency<IUserAccountKeysQuery>()
+            .Run(user)
+            .Returns(new UserAccountKeysData
+            {
+                PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData("wrappedPrivateKey", "publicKey", "signedPublicKey"),
+                SignatureKeyPairData = new SignatureKeyPairData(SignatureAlgorithm.Ed25519, "wrappedSigningKey", "verifyingKey"),
+            });
+
+        var result = await sutProvider.Sut.GetAccountKeysAsync(userId);
+        Assert.NotNull(result);
+        Assert.Equal("publicKey", result.PublicKey);
+        Assert.Equal("signedPublicKey", result.SignedPublicKey);
+        Assert.Equal("verifyingKey", result.VerifyingKey);
+    }
+
+    [Theory]
+    [BitAutoData]
+    public async Task GetAccountKeys_ReturnsPublicUserKeysResponseModel_WithNullVerifyingKey(
+        SutProvider<UsersController> sutProvider,
+        Guid userId)
+    {
+        var user = new User
+        {
+            Id = userId,
+            PublicKey = "publicKey",
+            SignedPublicKey = null,
+        };
+
+        sutProvider.GetDependency<IUserRepository>().GetByIdAsync(userId).Returns(user);
+        sutProvider.GetDependency<IUserAccountKeysQuery>()
+            .Run(user)
+            .Returns(new UserAccountKeysData
+            {
+                PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData("wrappedPrivateKey", "publicKey", null),
+                SignatureKeyPairData = null,
+            });
+
+        var result = await sutProvider.Sut.GetAccountKeysAsync(userId);
+        Assert.NotNull(result);
+        Assert.Equal("publicKey", result.PublicKey);
+        Assert.Null(result.SignedPublicKey);
+        Assert.Null(result.VerifyingKey);
+    }
+}

test/Api.Test/KeyManagement/Models/Request/SignatureKeyPairRequestModel.cs

@@ -0,0 +1,22 @@
+#nullable enable
+
+using Bit.Api.KeyManagement.Models.Requests;
+using Xunit;
+
+namespace Bit.Api.Test.KeyManagement.Models.Request;
+
+public class SignatureKeyPairRequestModelTests
+{
+    [Fact]
+    public void ToSignatureKeyPairData_WrongAlgorithm_Rejects()
+    {
+        var model = new SignatureKeyPairRequestModel
+        {
+            SignatureAlgorithm = "abc",
+            WrappedSigningKey = "wrappedKey",
+            VerifyingKey = "verifyingKey"
+        };
+
+        Assert.Throws<ArgumentException>(() => model.ToSignatureKeyPairData());
+    }
+}

test/Api.Test/Vault/Controllers/SyncControllerTests.cs

@@ -12,6 +12,8 @@ using Bit.Core.Auth.UserFeatures.TwoFactorAuth.Interfaces;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Data;
 using Bit.Core.Models.Data.Organizations.OrganizationUsers;
 using Bit.Core.Repositories;
@@ -74,6 +76,7 @@ public class SyncControllerTests
         var policyRepository = sutProvider.GetDependency<IPolicyRepository>();
         var collectionRepository = sutProvider.GetDependency<ICollectionRepository>();
         var collectionCipherRepository = sutProvider.GetDependency<ICollectionCipherRepository>();
+        var userAccountKeysQuery = sutProvider.GetDependency<IUserAccountKeysQuery>();
 
         // Adjust random data to match required formats / test intentions
         user.EquivalentDomains = JsonSerializer.Serialize(userEquivalentDomains);
@@ -98,6 +101,11 @@ public class SyncControllerTests
 
         // Setup returns
         userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).ReturnsForAnyArgs(user);
+        userAccountKeysQuery.Run(user).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            SignatureKeyPairData = null,
+        });
 
         organizationUserRepository
             .GetManyDetailsByUserAsync(user.Id, OrganizationUserStatusType.Confirmed).Returns(organizationUserDetails);
@@ -127,7 +135,6 @@ public class SyncControllerTests
         // Execute GET
         var result = await sutProvider.Sut.Get();
 
-
         // Asserts
         // Assert that methods are called
         var hasEnabledOrgs = organizationUserDetails.Any(o => o.Enabled);
@@ -166,6 +173,7 @@ public class SyncControllerTests
         var policyRepository = sutProvider.GetDependency<IPolicyRepository>();
         var collectionRepository = sutProvider.GetDependency<ICollectionRepository>();
         var collectionCipherRepository = sutProvider.GetDependency<ICollectionCipherRepository>();
+        var userAccountKeysQuery = sutProvider.GetDependency<IUserAccountKeysQuery>();
 
         // Adjust random data to match required formats / test intentions
         user.EquivalentDomains = JsonSerializer.Serialize(userEquivalentDomains);
@@ -189,6 +197,11 @@ public class SyncControllerTests
 
         // Setup returns
         userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).ReturnsForAnyArgs(user);
+        userAccountKeysQuery.Run(user).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            SignatureKeyPairData = null,
+        });
 
         organizationUserRepository
             .GetManyDetailsByUserAsync(user.Id, OrganizationUserStatusType.Confirmed).Returns(organizationUserDetails);
@@ -256,6 +269,7 @@ public class SyncControllerTests
         var policyRepository = sutProvider.GetDependency<IPolicyRepository>();
         var collectionRepository = sutProvider.GetDependency<ICollectionRepository>();
         var collectionCipherRepository = sutProvider.GetDependency<ICollectionCipherRepository>();
+        var userAccountKeysQuery = sutProvider.GetDependency<IUserAccountKeysQuery>();
 
         // Adjust random data to match required formats / test intentions
         user.EquivalentDomains = JsonSerializer.Serialize(userEquivalentDomains);
@@ -290,6 +304,12 @@ public class SyncControllerTests
         twoFactorIsEnabledQuery.TwoFactorIsEnabledAsync(user).Returns(false);
         userService.HasPremiumFromOrganization(user).Returns(false);
 
+        userAccountKeysQuery.Run(user).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            SignatureKeyPairData = null,
+        });
+
         // Execute GET
         var result = await sutProvider.Sut.Get();
 
@@ -327,6 +347,13 @@ public class SyncControllerTests
 
         user.MasterPassword = null;
 
+        var userAccountKeysQuery = sutProvider.GetDependency<IUserAccountKeysQuery>();
+        userAccountKeysQuery.Run(user).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            SignatureKeyPairData = null,
+        });
+
         var userService = sutProvider.GetDependency<IUserService>();
         userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).ReturnsForAnyArgs(user);
 
@@ -352,6 +379,13 @@ public class SyncControllerTests
         user.KdfMemory = kdfMemory;
         user.KdfParallelism = kdfParallelism;
 
+        var userAccountKeysQuery = sutProvider.GetDependency<IUserAccountKeysQuery>();
+        userAccountKeysQuery.Run(user).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = user.GetPublicKeyEncryptionKeyPair(),
+            SignatureKeyPairData = null,
+        });
+
         var userService = sutProvider.GetDependency<IUserService>();
         userService.GetUserByPrincipalAsync(Arg.Any<ClaimsPrincipal>()).ReturnsForAnyArgs(user);
 

test/Core.Test/KeyManagement/Queries/UserAccountKeysQuery.cs

@@ -0,0 +1,43 @@
+using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries;
+using Bit.Core.KeyManagement.Repositories;
+using Bit.Test.Common.AutoFixture;
+using Bit.Test.Common.AutoFixture.Attributes;
+using NSubstitute;
+using Xunit;
+
+namespace Bit.Core.Test.KeyManagement.Queries;
+
+[SutProviderCustomize]
+public class UserAccountKeysQueryTests
+{
+    [Theory, BitAutoData]
+    public async Task V1User_Success(SutProvider<UserAccountKeysQuery> sutProvider, User user)
+    {
+        var result = await sutProvider.Sut.Run(user);
+        Assert.Equal(user.GetPublicKeyEncryptionKeyPair().PublicKey, result.PublicKeyEncryptionKeyPairData.PublicKey);
+        Assert.Equal(user.GetPublicKeyEncryptionKeyPair().WrappedPrivateKey, result.PublicKeyEncryptionKeyPairData.WrappedPrivateKey);
+    }
+
+    [Theory, BitAutoData]
+    public async Task V2User_Success(SutProvider<UserAccountKeysQuery> sutProvider, User user)
+    {
+        user.SecurityState = "v2";
+        user.SecurityVersion = 2;
+        var signatureKeyPairRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        signatureKeyPairRepository.GetByUserIdAsync(user.Id).Returns(new SignatureKeyPairData(Core.KeyManagement.Enums.SignatureAlgorithm.Ed25519, "wrappedSigningKey", "verifyingKey"));
+        var result = await sutProvider.Sut.Run(user);
+        Assert.Equal(user.GetPublicKeyEncryptionKeyPair().PublicKey, result.PublicKeyEncryptionKeyPairData.PublicKey);
+        Assert.Equal(user.GetPublicKeyEncryptionKeyPair().WrappedPrivateKey, result.PublicKeyEncryptionKeyPairData.WrappedPrivateKey);
+        Assert.Equal(user.GetPublicKeyEncryptionKeyPair().SignedPublicKey, result.PublicKeyEncryptionKeyPairData.SignedPublicKey);
+
+        Assert.NotNull(result.SignatureKeyPairData);
+        Assert.Equal("wrappedSigningKey", result.SignatureKeyPairData.WrappedSigningKey);
+        Assert.Equal("verifyingKey", result.SignatureKeyPairData.VerifyingKey);
+
+        Assert.Equal(user.SecurityState, result.SecurityStateData.SecurityState);
+        Assert.Equal(user.GetSecurityVersion(), result.SecurityStateData.SecurityVersion);
+    }
+
+}

test/Core.Test/KeyManagement/UserKey/RotateUserAccountKeysCommandTests.cs

@@ -1,11 +1,18 @@
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Enums;
 using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Repositories;
 using Bit.Core.KeyManagement.UserKey.Implementations;
 using Bit.Core.Services;
+using Bit.Core.Tools.Entities;
+using Bit.Core.Tools.Repositories;
+using Bit.Core.Vault.Entities;
+using Bit.Core.Vault.Repositories;
 using Bit.Test.Common.AutoFixture;
 using Bit.Test.Common.AutoFixture.Attributes;
 using Microsoft.AspNetCore.Identity;
 using NSubstitute;
+using NSubstitute.ReturnsExtensions;
 using Xunit;
 
 namespace Bit.Core.Test.KeyManagement.UserKey;
@@ -14,7 +21,7 @@ namespace Bit.Core.Test.KeyManagement.UserKey;
 public class RotateUserAccountKeysCommandTests
 {
     [Theory, BitAutoData]
-    public async Task RejectsWrongOldMasterPassword(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+    public async Task RotateUserAccountKeysAsync_WrongOldMasterPassword_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
         RotateUserAccountKeysData model)
     {
         user.Email = model.MasterPasswordUnlockData.Email;
@@ -25,41 +32,38 @@ public class RotateUserAccountKeysCommandTests
 
         Assert.NotEqual(IdentityResult.Success, result);
     }
+
     [Theory, BitAutoData]
-    public async Task ThrowsWhenUserIsNull(SutProvider<RotateUserAccountKeysCommand> sutProvider,
+    public async Task RotateUserAccountKeysAsync_UserIsNull_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider,
           RotateUserAccountKeysData model)
     {
         await Assert.ThrowsAsync<ArgumentNullException>(async () => await sutProvider.Sut.RotateUserAccountKeysAsync(null, model));
     }
+
     [Theory, BitAutoData]
-    public async Task RejectsEmailChange(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+    public async Task RotateUserAccountKeysAsync_EmailChange_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
         RotateUserAccountKeysData model)
     {
-        user.Kdf = Enums.KdfType.Argon2id;
+        SetTestKdfAndSaltForUserAndModel(user, model);
-        user.KdfIterations = 3;
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
-        user.KdfMemory = 64;
+        SetV1ExistingUser(user, signatureRepository);
-        user.KdfParallelism = 4;
+        SetV1ModelUser(model);
 
         model.MasterPasswordUnlockData.Email = user.Email + ".different-domain";
-        model.MasterPasswordUnlockData.KdfType = Enums.KdfType.Argon2id;
-        model.MasterPasswordUnlockData.KdfIterations = 3;
-        model.MasterPasswordUnlockData.KdfMemory = 64;
-        model.MasterPasswordUnlockData.KdfParallelism = 4;
         sutProvider.GetDependency<IUserService>().CheckPasswordAsync(user, model.OldMasterKeyAuthenticationHash)
             .Returns(true);
         await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.RotateUserAccountKeysAsync(user, model));
     }
 
     [Theory, BitAutoData]
-    public async Task RejectsKdfChange(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+    public async Task RotateUserAccountKeysAsync_KdfChange_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
         RotateUserAccountKeysData model)
     {
-        user.Kdf = Enums.KdfType.Argon2id;
+        SetTestKdfAndSaltForUserAndModel(user, model);
-        user.KdfIterations = 3;
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
-        user.KdfMemory = 64;
+        SetV1ExistingUser(user, signatureRepository);
-        user.KdfParallelism = 4;
+        SetV1ModelUser(model);
 
-        model.MasterPasswordUnlockData.Email = user.Email;
         model.MasterPasswordUnlockData.KdfType = Enums.KdfType.PBKDF2_SHA256;
         model.MasterPasswordUnlockData.KdfIterations = 600000;
         model.MasterPasswordUnlockData.KdfMemory = null;
@@ -71,22 +75,15 @@ public class RotateUserAccountKeysCommandTests
 
 
     [Theory, BitAutoData]
-    public async Task RejectsPublicKeyChange(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+    public async Task RotateUserAccountKeysAsync_PublicKeyChange_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
         RotateUserAccountKeysData model)
     {
-        user.PublicKey = "old-public";
+        SetTestKdfAndSaltForUserAndModel(user, model);
-        user.Kdf = Enums.KdfType.Argon2id;
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
-        user.KdfIterations = 3;
+        SetV1ExistingUser(user, signatureRepository);
-        user.KdfMemory = 64;
+        SetV1ModelUser(model);
-        user.KdfParallelism = 4;
-
-        model.AccountPublicKey = "new-public";
-        model.MasterPasswordUnlockData.Email = user.Email;
-        model.MasterPasswordUnlockData.KdfType = Enums.KdfType.Argon2id;
-        model.MasterPasswordUnlockData.KdfIterations = 3;
-        model.MasterPasswordUnlockData.KdfMemory = 64;
-        model.MasterPasswordUnlockData.KdfParallelism = 4;
 
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.PublicKey = "new-public";
         sutProvider.GetDependency<IUserService>().CheckPasswordAsync(user, model.OldMasterKeyAuthenticationHash)
             .Returns(true);
 
@@ -94,27 +91,350 @@ public class RotateUserAccountKeysCommandTests
     }
 
     [Theory, BitAutoData]
-    public async Task RotatesCorrectly(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+    public async Task RotateUserAccountKeysAsync_V1_Success(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
         RotateUserAccountKeysData model)
     {
-        user.Kdf = Enums.KdfType.Argon2id;
+        SetTestKdfAndSaltForUserAndModel(user, model);
-        user.KdfIterations = 3;
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
-        user.KdfMemory = 64;
+        SetV1ExistingUser(user, signatureRepository);
-        user.KdfParallelism = 4;
+        SetV1ModelUser(model);
-
-        model.MasterPasswordUnlockData.Email = user.Email;
-        model.MasterPasswordUnlockData.KdfType = Enums.KdfType.Argon2id;
-        model.MasterPasswordUnlockData.KdfIterations = 3;
-        model.MasterPasswordUnlockData.KdfMemory = 64;
-        model.MasterPasswordUnlockData.KdfParallelism = 4;
-
-        model.AccountPublicKey = user.PublicKey;
 
         sutProvider.GetDependency<IUserService>().CheckPasswordAsync(user, model.OldMasterKeyAuthenticationHash)
             .Returns(true);
 
         var result = await sutProvider.Sut.RotateUserAccountKeysAsync(user, model);
-
         Assert.Equal(IdentityResult.Success, result);
     }
+
+    [Theory, BitAutoData]
+    public async Task RotateUserAccountKeysAsync_UpgradeV1ToV2_Success(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user,
+        RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+
+        sutProvider.GetDependency<IUserService>().CheckPasswordAsync(user, model.OldMasterKeyAuthenticationHash)
+            .Returns(true);
+
+        var result = await sutProvider.Sut.RotateUserAccountKeysAsync(user, model);
+        Assert.Equal(IdentityResult.Success, result);
+        Assert.Equal(user.SecurityState, model.AccountKeys.SecurityStateData!.SecurityState);
+    }
+
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_PublicKeyChange_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV1ModelUser(model);
+
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.PublicKey = "new-public";
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V2User_PrivateKeyNotXChaCha20_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey = "2.xxx";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V1User_PrivateKeyNotAesCbcHmac_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV1ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey = "7.xxx";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("The provided account private key was not wrapped with AES-256-CBC-HMAC", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V1_Success(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV1ModelUser(model);
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions);
+        Assert.Empty(saveEncryptedDataActions);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V2_Success(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions);
+        Assert.NotEmpty(saveEncryptedDataActions);
+        Assert.Equal(user.SecurityState, model.AccountKeys.SecurityStateData!.SecurityState);
+    }
+
+
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V2User_VerifyingKeyMismatch_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.SignatureKeyPairData.VerifyingKey = "different-verifying-key";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("The provided verifying key does not match the user's current verifying key.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V2User_SignedPublicKeyNullOrEmpty_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey = null;
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("No signed public key provided, but the user already has a signature key pair.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_V2User_WrappedSigningKeyNotXChaCha20_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.SignatureKeyPairData.WrappedSigningKey = "2.xxx";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("The provided signing key data is not wrapped with XChaCha20-Poly1305.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeys_UpgradeToV2_InvalidVerifyingKey_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.SignatureKeyPairData.VerifyingKey = "";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("The provided signature key pair data does not contain a valid verifying key.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_UpgradeToV2_IncorrectlyWrappedPrivateKey_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey = "2.abc";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("The provided private key encryption key is not wrapped with XChaCha20-Poly1305.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_UpgradeToV2_NoSignedPublicKey_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.SignedPublicKey = null;
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("No signed public key provided, but the user already has a signature key pair.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_UpgradeToV2_NoSecurityState_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.SecurityStateData = null;
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("No signed security state provider for V2 user", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_RotateV2_NoSignatureKeyPair_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV2ExistingUser(user, signatureRepository);
+        SetV2ModelUser(model);
+        model.AccountKeys.SignatureKeyPairData = null;
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<InvalidOperationException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("Signature key pair data is required for V2 encryption.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_GetEncryptionType_EmptyString_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV1ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey = "";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<ArgumentException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("Invalid encryption type string.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateAccountKeysAsync_GetEncryptionType_InvalidString_Rejects(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        SetTestKdfAndSaltForUserAndModel(user, model);
+        var signatureRepository = sutProvider.GetDependency<IUserSignatureKeyPairRepository>();
+        SetV1ExistingUser(user, signatureRepository);
+        SetV1ModelUser(model);
+        model.AccountKeys.PublicKeyEncryptionKeyPairData.WrappedPrivateKey = "9.xxx";
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+        var ex = await Assert.ThrowsAsync<ArgumentException>(async () => await sutProvider.Sut.UpdateAccountKeysAsync(model, user, saveEncryptedDataActions));
+        Assert.Equal("Invalid encryption type string.", ex.Message);
+    }
+
+    [Theory, BitAutoData]
+    public async Task UpdateUserData_RevisionDateChanged_Success(SutProvider<RotateUserAccountKeysCommand> sutProvider, User user, RotateUserAccountKeysData model)
+    {
+        var oldDate = new DateTime(2017, 1, 1);
+
+        var cipher = Substitute.For<Cipher>();
+        cipher.RevisionDate = oldDate;
+        model.Ciphers = [cipher];
+
+        var folder = Substitute.For<Folder>();
+        folder.RevisionDate = oldDate;
+        model.Folders = [folder];
+
+        var send = Substitute.For<Send>();
+        send.RevisionDate = oldDate;
+        model.Sends = [send];
+
+        var saveEncryptedDataActions = new List<Core.KeyManagement.UserKey.UpdateEncryptedDataForKeyRotation>();
+
+        sutProvider.Sut.UpdateUserData(model, user, saveEncryptedDataActions);
+        foreach (var dataAction in saveEncryptedDataActions)
+        {
+            await dataAction.Invoke();
+        }
+
+        var updatedCiphers = sutProvider.GetDependency<ICipherRepository>()
+            .ReceivedCalls()
+            .FirstOrDefault(call => call.GetMethodInfo().Name == "UpdateForKeyRotation")?
+            .GetArguments()[1] as IEnumerable<Cipher>;
+        foreach (var updatedCipher in updatedCiphers!)
+        {
+            var oldCipher = model.Ciphers.FirstOrDefault(c => c.Id == updatedCipher.Id);
+            Assert.NotEqual(oldDate, updatedCipher.RevisionDate);
+        }
+
+        var updatedFolders = sutProvider.GetDependency<IFolderRepository>()
+            .ReceivedCalls()
+            .FirstOrDefault(call => call.GetMethodInfo().Name == "UpdateForKeyRotation")?
+            .GetArguments()[1] as IEnumerable<Folder>;
+        foreach (var updatedFolder in updatedFolders!)
+        {
+            var oldFolder = model.Folders.FirstOrDefault(f => f.Id == updatedFolder.Id);
+            Assert.NotEqual(oldDate, updatedFolder.RevisionDate);
+        }
+
+        var updatedSends = sutProvider.GetDependency<ISendRepository>()
+            .ReceivedCalls()
+            .FirstOrDefault(call => call.GetMethodInfo().Name == "UpdateForKeyRotation")?
+            .GetArguments()[1] as IEnumerable<Send>;
+        foreach (var updatedSend in updatedSends!)
+        {
+            var oldSend = model.Sends.FirstOrDefault(s => s.Id == updatedSend.Id);
+            Assert.NotEqual(oldDate, updatedSend.RevisionDate);
+        }
+    }
+
+    // Helper functions to set valid test parameters that match each other to the model and user. 
+    private static void SetTestKdfAndSaltForUserAndModel(User user, RotateUserAccountKeysData model)
+    {
+        user.Kdf = Enums.KdfType.Argon2id;
+        user.KdfIterations = 3;
+        user.KdfMemory = 64;
+        user.KdfParallelism = 4;
+        model.MasterPasswordUnlockData.KdfType = Enums.KdfType.Argon2id;
+        model.MasterPasswordUnlockData.KdfIterations = 3;
+        model.MasterPasswordUnlockData.KdfMemory = 64;
+        model.MasterPasswordUnlockData.KdfParallelism = 4;
+        // The email is the salt for the KDF and is validated currently.
+        user.Email = model.MasterPasswordUnlockData.Email;
+    }
+
+    private static void SetV1ExistingUser(User user, IUserSignatureKeyPairRepository userSignatureKeyPairRepository)
+    {
+        user.PrivateKey = "2.abc";
+        user.PublicKey = "public";
+        user.SignedPublicKey = null;
+        userSignatureKeyPairRepository.GetByUserIdAsync(user.Id).ReturnsNull();
+    }
+
+    private static void SetV2ExistingUser(User user, IUserSignatureKeyPairRepository userSignatureKeyPairRepository)
+    {
+        user.PrivateKey = "7.abc";
+        user.PublicKey = "public";
+        user.SignedPublicKey = "signed-public";
+        userSignatureKeyPairRepository.GetByUserIdAsync(user.Id).Returns(new SignatureKeyPairData(SignatureAlgorithm.Ed25519, "7.abc", "verifying-key"));
+    }
+
+    private static void SetV1ModelUser(RotateUserAccountKeysData model)
+    {
+        model.AccountKeys.PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData("2.abc", "public", null);
+        model.AccountKeys.SignatureKeyPairData = null;
+        model.AccountKeys.SecurityStateData = null;
+    }
+
+    private static void SetV2ModelUser(RotateUserAccountKeysData model)
+    {
+        model.AccountKeys.PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData("7.abc", "public", "signed-public");
+        model.AccountKeys.SignatureKeyPairData = new SignatureKeyPairData(SignatureAlgorithm.Ed25519, "7.abc", "verifying-key");
+        model.AccountKeys.SecurityStateData = new SecurityStateData
+        {
+            SecurityState = "abc",
+            SecurityVersion = 2,
+        };
+    }
 }

test/Identity.Test/IdentityServer/BaseRequestValidatorTests.cs

@@ -10,7 +10,9 @@ using Bit.Core.Auth.Repositories;
 using Bit.Core.Context;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
-using Bit.Core.KeyManagement.Models.Response;
+using Bit.Core.KeyManagement.Models.Api.Response;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Models.Api;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -51,6 +53,7 @@ public class BaseRequestValidatorTests
     private readonly IPolicyRequirementQuery _policyRequirementQuery;
     private readonly IAuthRequestRepository _authRequestRepository;
     private readonly IMailService _mailService;
+    private readonly IUserAccountKeysQuery _userAccountKeysQuery;
 
     private readonly BaseRequestValidatorTestWrapper _sut;
 
@@ -73,6 +76,7 @@ public class BaseRequestValidatorTests
         _policyRequirementQuery = Substitute.For<IPolicyRequirementQuery>();
         _authRequestRepository = Substitute.For<IAuthRequestRepository>();
         _mailService = Substitute.For<IMailService>();
+        _userAccountKeysQuery = Substitute.For<IUserAccountKeysQuery>();
 
         _sut = new BaseRequestValidatorTestWrapper(
             _userManager,
@@ -91,7 +95,8 @@ public class BaseRequestValidatorTests
             _userDecryptionOptionsBuilder,
             _policyRequirementQuery,
             _authRequestRepository,
-            _mailService);
+            _mailService,
+            _userAccountKeysQuery);
     }
 
     /* Logic path
@@ -180,6 +185,13 @@ public class BaseRequestValidatorTests
         // 5 -> not legacy user
         _userService.IsLegacyUser(Arg.Any<string>())
             .Returns(false);
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         // Act
         await _sut.ValidateAsync(context);
@@ -227,6 +239,13 @@ public class BaseRequestValidatorTests
         // 5 -> not legacy user
         _userService.IsLegacyUser(Arg.Any<string>())
             .Returns(false);
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         // Act
         await _sut.ValidateAsync(context);
@@ -460,6 +479,13 @@ public class BaseRequestValidatorTests
             .Returns(Task.FromResult(new Tuple<bool, Organization>(false, null)));
         _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
             .Returns(Task.FromResult(true));
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         await _sut.ValidateAsync(context);
 
@@ -495,6 +521,13 @@ public class BaseRequestValidatorTests
         _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
             .Returns(Task.FromResult(true));
         context.ValidatedTokenRequest.ClientId = "web";
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         // Act
         await _sut.ValidateAsync(context);
@@ -529,6 +562,13 @@ public class BaseRequestValidatorTests
         _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
             .Returns(Task.FromResult(true));
         context.ValidatedTokenRequest.ClientId = "web";
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         // Act
         await _sut.ValidateAsync(context);
@@ -591,6 +631,13 @@ public class BaseRequestValidatorTests
             HasMasterPassword = false,
             MasterPasswordUnlock = null
         }));
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
 
         var context = CreateContext(tokenRequest, requestContext, grantResult);
         _sut.isValid = true;
@@ -644,6 +691,14 @@ public class BaseRequestValidatorTests
             }
         }));
 
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
+
         var context = CreateContext(tokenRequest, requestContext, grantResult);
         _sut.isValid = true;
 
@@ -671,6 +726,152 @@ public class BaseRequestValidatorTests
         Assert.Equal("test@example.com", userDecryptionOptions.MasterPasswordUnlock.Salt);
     }
 
+    [Theory, BitAutoData]
+    public async Task ValidateAsync_CustomResponse_ShouldIncludeAccountKeys(
+        [AuthFixtures.ValidatedTokenRequest] ValidatedTokenRequest tokenRequest,
+        CustomValidatorRequestContext requestContext,
+        GrantValidationResult grantResult)
+    {
+        // Arrange
+        var mockAccountKeys = new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key",
+                "test-signed-public-key"
+            ),
+            SignatureKeyPairData = new SignatureKeyPairData(
+                Core.KeyManagement.Enums.SignatureAlgorithm.Ed25519,
+                "test-wrapped-signing-key",
+                "test-verifying-key"
+            ),
+            SecurityStateData = new SecurityStateData
+            {
+                SecurityState = "test-security-state",
+                SecurityVersion = 2
+            }
+        };
+
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(mockAccountKeys);
+
+        _userDecryptionOptionsBuilder.ForUser(Arg.Any<User>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithDevice(Arg.Any<Device>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithSso(Arg.Any<SsoConfig>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithWebAuthnLoginCredential(Arg.Any<WebAuthnCredential>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.BuildAsync().Returns(Task.FromResult(new UserDecryptionOptions
+        {
+            HasMasterPassword = true,
+            MasterPasswordUnlock = new MasterPasswordUnlockResponseModel
+            {
+                Kdf = new MasterPasswordUnlockKdfResponseModel
+                {
+                    KdfType = KdfType.PBKDF2_SHA256,
+                    Iterations = 100000
+                },
+                MasterKeyEncryptedUserKey = _mockEncryptedString,
+                Salt = "test@example.com"
+            }
+        }));
+
+        var context = CreateContext(tokenRequest, requestContext, grantResult);
+        _sut.isValid = true;
+
+        _twoFactorAuthenticationValidator.RequiresTwoFactorAsync(requestContext.User, tokenRequest)
+            .Returns(Task.FromResult(new Tuple<bool, Organization>(false, null)));
+        _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
+            .Returns(Task.FromResult(true));
+
+        // Act
+        await _sut.ValidateAsync(context);
+
+        // Assert
+        Assert.False(context.GrantResult.IsError);
+        var customResponse = context.GrantResult.CustomResponse;
+
+        // Verify AccountKeys are included in response
+        Assert.Contains("AccountKeys", customResponse);
+        Assert.IsType<PrivateKeysResponseModel>(customResponse["AccountKeys"]);
+
+        var accountKeysResponse = (PrivateKeysResponseModel)customResponse["AccountKeys"];
+        Assert.NotNull(accountKeysResponse.PublicKeyEncryptionKeyPair);
+        Assert.Equal("test-public-key", accountKeysResponse.PublicKeyEncryptionKeyPair.PublicKey);
+        Assert.Equal("test-private-key", accountKeysResponse.PublicKeyEncryptionKeyPair.WrappedPrivateKey);
+        Assert.Equal("test-signed-public-key", accountKeysResponse.PublicKeyEncryptionKeyPair.SignedPublicKey);
+
+        Assert.NotNull(accountKeysResponse.SignatureKeyPair);
+        Assert.Equal("test-wrapped-signing-key", accountKeysResponse.SignatureKeyPair.WrappedSigningKey);
+        Assert.Equal("test-verifying-key", accountKeysResponse.SignatureKeyPair.VerifyingKey);
+
+        Assert.NotNull(accountKeysResponse.SecurityState);
+        Assert.Equal("test-security-state", accountKeysResponse.SecurityState.SecurityState);
+        Assert.Equal(2, accountKeysResponse.SecurityState.SecurityVersion);
+    }
+    [Theory, BitAutoData]
+    public async Task ValidateAsync_CustomResponse_AccountKeysQuery_SkippedWhenPrivateKeyIsNull(
+           [AuthFixtures.ValidatedTokenRequest] ValidatedTokenRequest tokenRequest,
+           CustomValidatorRequestContext requestContext,
+           GrantValidationResult grantResult)
+    {
+        // Arrange
+        requestContext.User.PrivateKey = null;
+
+        var context = CreateContext(tokenRequest, requestContext, grantResult);
+        _sut.isValid = true;
+        _twoFactorAuthenticationValidator.RequiresTwoFactorAsync(requestContext.User, tokenRequest)
+            .Returns(Task.FromResult(new Tuple<bool, Organization>(false, null)));
+        _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
+            .Returns(Task.FromResult(true));
+
+        // Act
+        await _sut.ValidateAsync(context);
+
+        // Assert
+        Assert.False(context.GrantResult.IsError);
+
+        // Verify that the account keys query wasn't called.
+        await _userAccountKeysQuery.Received(0).Run(Arg.Any<User>());
+    }
+    [Theory, BitAutoData]
+    public async Task ValidateAsync_CustomResponse_AccountKeysQuery_CalledWithCorrectUser(
+        [AuthFixtures.ValidatedTokenRequest] ValidatedTokenRequest tokenRequest,
+        CustomValidatorRequestContext requestContext,
+        GrantValidationResult grantResult)
+    {
+        // Arrange
+        var expectedUser = requestContext.User;
+
+        _userAccountKeysQuery.Run(Arg.Any<User>()).Returns(new UserAccountKeysData
+        {
+            PublicKeyEncryptionKeyPairData = new PublicKeyEncryptionKeyPairData(
+                "test-private-key",
+                "test-public-key"
+            )
+        });
+
+        _userDecryptionOptionsBuilder.ForUser(Arg.Any<User>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithDevice(Arg.Any<Device>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithSso(Arg.Any<SsoConfig>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.WithWebAuthnLoginCredential(Arg.Any<WebAuthnCredential>()).Returns(_userDecryptionOptionsBuilder);
+        _userDecryptionOptionsBuilder.BuildAsync().Returns(Task.FromResult(new UserDecryptionOptions()));
+
+        var context = CreateContext(tokenRequest, requestContext, grantResult);
+        _sut.isValid = true;
+
+        _twoFactorAuthenticationValidator.RequiresTwoFactorAsync(requestContext.User, tokenRequest)
+            .Returns(Task.FromResult(new Tuple<bool, Organization>(false, null)));
+        _deviceValidator.ValidateRequestDeviceAsync(tokenRequest, requestContext)
+            .Returns(Task.FromResult(true));
+
+        // Act
+        await _sut.ValidateAsync(context);
+
+        // Assert
+        Assert.False(context.GrantResult.IsError);
+
+        // Verify that the account keys query was called with the correct user
+        await _userAccountKeysQuery.Received(1).Run(Arg.Is<User>(u => u.Id == expectedUser.Id));
+    }
+
     private BaseRequestValidationContextFake CreateContext(
         ValidatedTokenRequest tokenRequest,
         CustomValidatorRequestContext requestContext,

test/Identity.Test/Wrappers/BaseRequestValidatorTestWrapper.cs

@@ -4,6 +4,7 @@ using Bit.Core.AdminConsole.Services;
 using Bit.Core.Auth.Repositories;
 using Bit.Core.Context;
 using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Queries.Interfaces;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Settings;
@@ -64,7 +65,8 @@ IBaseRequestValidatorTestWrapper
         IUserDecryptionOptionsBuilder userDecryptionOptionsBuilder,
         IPolicyRequirementQuery policyRequirementQuery,
         IAuthRequestRepository authRequestRepository,
-        IMailService mailService) :
+        IMailService mailService,
+        IUserAccountKeysQuery userAccountKeysQuery) :
          base(
             userManager,
             userService,
@@ -82,7 +84,8 @@ IBaseRequestValidatorTestWrapper
             userDecryptionOptionsBuilder,
             policyRequirementQuery,
             authRequestRepository,
-            mailService)
+            mailService,
+            userAccountKeysQuery)
     {
     }
 

test/Infrastructure.EFIntegration.Test/AutoFixture/EntityFrameworkRepositoryFixtures.cs

@@ -92,6 +92,7 @@ public class EfRepositoryListBuilder<T> : ISpecimenBuilder where T : BaseEntityF
                     cfg.AddProfile<TransactionMapperProfile>();
                     cfg.AddProfile<UserMapperProfile>();
                     cfg.AddProfile<PasswordHealthReportApplicationProfile>();
+                    cfg.AddProfile<UserSignatureKeyPairMapperProfile>();
                     cfg.AddProfile<OrganizationReportProfile>();
                 })
             .CreateMapper()));

test/Infrastructure.EFIntegration.Test/Repositories/EqualityComparers/UserCompare.cs

@@ -29,7 +29,8 @@ public class UserCompare : IEqualityComparer<User>
                 x.LicenseKey == y.LicenseKey &&
                 x.ApiKey == y.ApiKey &&
                 x.Kdf == y.Kdf &&
-                x.KdfIterations == y.KdfIterations;
+                x.KdfIterations == y.KdfIterations &&
+                x.SignedPublicKey == y.SignedPublicKey;
     }
 
     public int GetHashCode([DisallowNull] User obj)

util/Migrator/DbScripts/2025-10-13_00_UserCryptoV2.sql

@@ -0,0 +1,396 @@
+IF OBJECT_ID('[dbo].[UserSignatureKeyPair]') IS NULL
+BEGIN
+    CREATE TABLE [dbo].[UserSignatureKeyPair]
+    (
+        [Id] UNIQUEIDENTIFIER NOT NULL,
+        [UserId] UNIQUEIDENTIFIER NOT NULL,
+        [SignatureAlgorithm] TINYINT NOT NULL,
+        [SigningKey] VARCHAR(MAX) NOT NULL,
+        [VerifyingKey] VARCHAR(MAX) NOT NULL,
+        [CreationDate] DATETIME2 (7) NOT NULL,
+        [RevisionDate] DATETIME2 (7) NOT NULL,
+        CONSTRAINT [PK_UserSignatureKeyPair] PRIMARY KEY CLUSTERED ([Id] ASC),
+        CONSTRAINT [FK_UserSignatureKeyPair_User] FOREIGN KEY ([UserId]) REFERENCES [dbo].[User] ([Id]) ON DELETE CASCADE
+    );
+END
+GO
+
+IF NOT EXISTS(SELECT name
+FROM sys.indexes
+WHERE name = 'IX_UserSignatureKeyPair_UserId')
+BEGIN
+CREATE UNIQUE NONCLUSTERED INDEX [IX_UserSignatureKeyPair_UserId]
+    ON [dbo].[UserSignatureKeyPair]([UserId] ASC);
+END
+GO
+
+
+CREATE OR ALTER VIEW [dbo].[UserSignatureKeyPairView]
+AS
+SELECT
+    *
+FROM
+    [dbo].[UserSignatureKeyPair]
+GO
+
+CREATE OR ALTER PROCEDURE [dbo].[UserSignatureKeyPair_ReadByUserId]
+    @UserId UNIQUEIDENTIFIER
+AS
+BEGIN
+    SET NOCOUNT ON;
+
+    SELECT
+        *
+    FROM
+        [dbo].[UserSignatureKeyPairView]
+    WHERE
+        [UserId] = @UserId;
+END
+GO
+
+CREATE OR ALTER PROCEDURE [dbo].[UserSignatureKeyPair_UpdateForRotation]
+    @UserId UNIQUEIDENTIFIER,
+    @SignatureAlgorithm TINYINT,
+    @SigningKey VARCHAR(MAX),
+    @VerifyingKey VARCHAR(MAX),
+    @RevisionDate DATETIME2(7)
+AS
+BEGIN
+    SET NOCOUNT ON;
+
+    UPDATE
+        [dbo].[UserSignatureKeyPair]
+    SET 
+        [SignatureAlgorithm] = @SignatureAlgorithm,
+        [SigningKey] = @SigningKey,
+        [VerifyingKey] = @VerifyingKey,
+        [RevisionDate] = @RevisionDate
+    WHERE
+        [UserId] = @UserId;
+END
+GO
+
+CREATE OR ALTER PROCEDURE [dbo].[UserSignatureKeyPair_SetForRotation]
+    @Id UNIQUEIDENTIFIER,
+    @UserId UNIQUEIDENTIFIER,
+    @SignatureAlgorithm TINYINT,
+    @SigningKey VARCHAR(MAX),
+    @VerifyingKey VARCHAR(MAX),
+    @CreationDate DATETIME2(7),
+    @RevisionDate DATETIME2(7)
+AS
+BEGIN
+    SET NOCOUNT ON;
+
+    INSERT INTO [dbo].[UserSignatureKeyPair] 
+    (
+        [Id], 
+        [UserId], 
+        [SignatureAlgorithm], 
+        [SigningKey], 
+        [VerifyingKey], 
+        [CreationDate], 
+        [RevisionDate]
+    )
+    VALUES 
+    (
+        @Id, 
+        @UserId, 
+        @SignatureAlgorithm, 
+        @SigningKey, 
+        @VerifyingKey, 
+        @CreationDate, 
+        @RevisionDate
+    )
+END
+GO
+
+IF COL_LENGTH('[dbo].[User]', 'SecurityState') IS NULL
+BEGIN
+    ALTER TABLE
+        [dbo].[User]
+    ADD
+        [SecurityState] VARCHAR(MAX) NULL;
+END
+GO
+
+IF COL_LENGTH('[dbo].[User]', 'SecurityVersion') IS NULL
+BEGIN
+    ALTER TABLE
+        [dbo].[User]
+    ADD
+        [SecurityVersion] INT NULL;
+END
+GO
+
+IF COL_LENGTH('[dbo].[User]', 'SignedPublicKey') IS NULL
+BEGIN
+    ALTER TABLE
+        [dbo].[User]
+    ADD
+        [SignedPublicKey] VARCHAR(MAX) NULL;
+END
+GO
+
+CREATE OR ALTER PROCEDURE [dbo].[User_Create]
+    @Id UNIQUEIDENTIFIER OUTPUT,
+    @Name NVARCHAR(50),
+    @Email NVARCHAR(256),
+    @EmailVerified BIT,
+    @MasterPassword NVARCHAR(300),
+    @MasterPasswordHint NVARCHAR(50),
+    @Culture NVARCHAR(10),
+    @SecurityStamp NVARCHAR(50),
+    @TwoFactorProviders NVARCHAR(MAX),
+    @TwoFactorRecoveryCode NVARCHAR(32),
+    @EquivalentDomains NVARCHAR(MAX),
+    @ExcludedGlobalEquivalentDomains NVARCHAR(MAX),
+    @AccountRevisionDate DATETIME2(7),
+    @Key NVARCHAR(MAX),
+    @PublicKey NVARCHAR(MAX),
+    @PrivateKey NVARCHAR(MAX),
+    @Premium BIT,
+    @PremiumExpirationDate DATETIME2(7),
+    @RenewalReminderDate DATETIME2(7),
+    @Storage BIGINT,
+    @MaxStorageGb SMALLINT,
+    @Gateway TINYINT,
+    @GatewayCustomerId VARCHAR(50),
+    @GatewaySubscriptionId VARCHAR(50),
+    @ReferenceData VARCHAR(MAX),
+    @LicenseKey VARCHAR(100),
+    @Kdf TINYINT,
+    @KdfIterations INT,
+    @KdfMemory INT = NULL,
+    @KdfParallelism INT = NULL,
+    @CreationDate DATETIME2(7),
+    @RevisionDate DATETIME2(7),
+    @ApiKey VARCHAR(30),
+    @ForcePasswordReset BIT = 0,
+    @UsesKeyConnector BIT = 0,
+    @FailedLoginCount INT = 0,
+    @LastFailedLoginDate DATETIME2(7),
+    @AvatarColor VARCHAR(7) = NULL,
+    @LastPasswordChangeDate DATETIME2(7) = NULL,
+    @LastKdfChangeDate DATETIME2(7) = NULL,
+    @LastKeyRotationDate DATETIME2(7) = NULL,
+    @LastEmailChangeDate DATETIME2(7) = NULL,
+    @VerifyDevices BIT = 1,
+    @SecurityState VARCHAR(MAX) = NULL,
+    @SecurityVersion INT = NULL,
+    @SignedPublicKey VARCHAR(MAX) = NULL
+AS
+BEGIN
+    SET NOCOUNT ON
+
+    INSERT INTO [dbo].[User]
+    (
+        [Id],
+        [Name],
+        [Email],
+        [EmailVerified],
+        [MasterPassword],
+        [MasterPasswordHint],
+        [Culture],
+        [SecurityStamp],
+        [TwoFactorProviders],
+        [TwoFactorRecoveryCode],
+        [EquivalentDomains],
+        [ExcludedGlobalEquivalentDomains],
+        [AccountRevisionDate],
+        [Key],
+        [PublicKey],
+        [PrivateKey],
+        [Premium],
+        [PremiumExpirationDate],
+        [RenewalReminderDate],
+        [Storage],
+        [MaxStorageGb],
+        [Gateway],
+        [GatewayCustomerId],
+        [GatewaySubscriptionId],
+        [ReferenceData],
+        [LicenseKey],
+        [Kdf],
+        [KdfIterations],
+        [CreationDate],
+        [RevisionDate],
+        [ApiKey],
+        [ForcePasswordReset],
+        [UsesKeyConnector],
+        [FailedLoginCount],
+        [LastFailedLoginDate],
+        [AvatarColor],
+        [KdfMemory],
+        [KdfParallelism],
+        [LastPasswordChangeDate],
+        [LastKdfChangeDate],
+        [LastKeyRotationDate],
+        [LastEmailChangeDate],
+        [VerifyDevices],
+        [SecurityState],
+        [SecurityVersion],
+        [SignedPublicKey]
+    )
+    VALUES
+    (
+        @Id,
+        @Name,
+        @Email,
+        @EmailVerified,
+        @MasterPassword,
+        @MasterPasswordHint,
+        @Culture,
+        @SecurityStamp,
+        @TwoFactorProviders,
+        @TwoFactorRecoveryCode,
+        @EquivalentDomains,
+        @ExcludedGlobalEquivalentDomains,
+        @AccountRevisionDate,
+        @Key,
+        @PublicKey,
+        @PrivateKey,
+        @Premium,
+        @PremiumExpirationDate,
+        @RenewalReminderDate,
+        @Storage,
+        @MaxStorageGb,
+        @Gateway,
+        @GatewayCustomerId,
+        @GatewaySubscriptionId,
+        @ReferenceData,
+        @LicenseKey,
+        @Kdf,
+        @KdfIterations,
+        @CreationDate,
+        @RevisionDate,
+        @ApiKey,
+        @ForcePasswordReset,
+        @UsesKeyConnector,
+        @FailedLoginCount,
+        @LastFailedLoginDate,
+        @AvatarColor,
+        @KdfMemory,
+        @KdfParallelism,
+        @LastPasswordChangeDate,
+        @LastKdfChangeDate,
+        @LastKeyRotationDate,
+        @LastEmailChangeDate,
+        @VerifyDevices,
+        @SecurityState,
+        @SecurityVersion,
+        @SignedPublicKey
+    )
+END
+GO
+
+CREATE OR ALTER PROCEDURE [dbo].[User_Update]
+    @Id UNIQUEIDENTIFIER,
+    @Name NVARCHAR(50),
+    @Email NVARCHAR(256),
+    @EmailVerified BIT,
+    @MasterPassword NVARCHAR(300),
+    @MasterPasswordHint NVARCHAR(50),
+    @Culture NVARCHAR(10),
+    @SecurityStamp NVARCHAR(50),
+    @TwoFactorProviders NVARCHAR(MAX),
+    @TwoFactorRecoveryCode NVARCHAR(32),
+    @EquivalentDomains NVARCHAR(MAX),
+    @ExcludedGlobalEquivalentDomains NVARCHAR(MAX),
+    @AccountRevisionDate DATETIME2(7),
+    @Key NVARCHAR(MAX),
+    @PublicKey NVARCHAR(MAX),
+    @PrivateKey NVARCHAR(MAX),
+    @Premium BIT,
+    @PremiumExpirationDate DATETIME2(7),
+    @RenewalReminderDate DATETIME2(7),
+    @Storage BIGINT,
+    @MaxStorageGb SMALLINT,
+    @Gateway TINYINT,
+    @GatewayCustomerId VARCHAR(50),
+    @GatewaySubscriptionId VARCHAR(50),
+    @ReferenceData VARCHAR(MAX),
+    @LicenseKey VARCHAR(100),
+    @Kdf TINYINT,
+    @KdfIterations INT,
+    @KdfMemory INT = NULL,
+    @KdfParallelism INT = NULL,
+    @CreationDate DATETIME2(7),
+    @RevisionDate DATETIME2(7),
+    @ApiKey VARCHAR(30),
+    @ForcePasswordReset BIT = 0,
+    @UsesKeyConnector BIT = 0,
+    @FailedLoginCount INT,
+    @LastFailedLoginDate DATETIME2(7),
+    @AvatarColor VARCHAR(7),
+    @LastPasswordChangeDate DATETIME2(7) = NULL,
+    @LastKdfChangeDate DATETIME2(7) = NULL,
+    @LastKeyRotationDate DATETIME2(7) = NULL,
+    @LastEmailChangeDate DATETIME2(7) = NULL,
+    @VerifyDevices BIT = 1,
+    @SecurityState VARCHAR(MAX) = NULL,
+    @SecurityVersion INT = NULL,
+    @SignedPublicKey VARCHAR(MAX) = NULL
+AS
+BEGIN
+    SET NOCOUNT ON
+
+    UPDATE
+        [dbo].[User]
+    SET
+        [Name] = @Name,
+        [Email] = @Email,
+        [EmailVerified] = @EmailVerified,
+        [MasterPassword] = @MasterPassword,
+        [MasterPasswordHint] = @MasterPasswordHint,
+        [Culture] = @Culture,
+        [SecurityStamp] = @SecurityStamp,
+        [TwoFactorProviders] = @TwoFactorProviders,
+        [TwoFactorRecoveryCode] = @TwoFactorRecoveryCode,
+        [EquivalentDomains] = @EquivalentDomains,
+        [ExcludedGlobalEquivalentDomains] = @ExcludedGlobalEquivalentDomains,
+        [AccountRevisionDate] = @AccountRevisionDate,
+        [Key] = @Key,
+        [PublicKey] = @PublicKey,
+        [PrivateKey] = @PrivateKey,
+        [Premium] = @Premium,
+        [PremiumExpirationDate] = @PremiumExpirationDate,
+        [RenewalReminderDate] = @RenewalReminderDate,
+        [Storage] = @Storage,
+        [MaxStorageGb] = @MaxStorageGb,
+        [Gateway] = @Gateway,
+        [GatewayCustomerId] = @GatewayCustomerId,
+        [GatewaySubscriptionId] = @GatewaySubscriptionId,
+        [ReferenceData] = @ReferenceData,
+        [LicenseKey] = @LicenseKey,
+        [Kdf] = @Kdf,
+        [KdfIterations] = @KdfIterations,
+        [KdfMemory] = @KdfMemory,
+        [KdfParallelism] = @KdfParallelism,
+        [CreationDate] = @CreationDate,
+        [RevisionDate] = @RevisionDate,
+        [ApiKey] = @ApiKey,
+        [ForcePasswordReset] = @ForcePasswordReset,
+        [UsesKeyConnector] = @UsesKeyConnector,
+        [FailedLoginCount] = @FailedLoginCount,
+        [LastFailedLoginDate] = @LastFailedLoginDate,
+        [AvatarColor] = @AvatarColor,
+        [LastPasswordChangeDate] = @LastPasswordChangeDate,
+        [LastKdfChangeDate] = @LastKdfChangeDate,
+        [LastKeyRotationDate] = @LastKeyRotationDate,
+        [LastEmailChangeDate] = @LastEmailChangeDate,
+        [VerifyDevices] = @VerifyDevices,
+        [SecurityState] = @SecurityState,
+        [SecurityVersion] = @SecurityVersion,
+        [SignedPublicKey] = @SignedPublicKey
+    WHERE
+        [Id] = @Id
+END
+GO
+
+EXECUTE sp_refreshview 'dbo.UserView'
+EXECUTE sp_refreshview 'dbo.EmergencyAccessDetailsView'
+EXECUTE sp_refreshview 'dbo.OrganizationUserUserDetailsView'
+EXECUTE sp_refreshview 'dbo.ProviderUserUserDetailsView'
+EXECUTE sp_refreshview 'dbo.UserEmailDomainView'   
+GO

util/MySqlMigrations/Migrations/20251013083703_UserCryptoV2.cs

@@ -0,0 +1,84 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace Bit.MySqlMigrations.Migrations;
+
+/// <inheritdoc />
+public partial class UserCryptoV2 : Migration
+{
+    /// <inheritdoc />
+    protected override void Up(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.AddColumn<string>(
+            name: "SecurityState",
+            table: "User",
+            type: "longtext",
+            nullable: true)
+            .Annotation("MySql:CharSet", "utf8mb4");
+
+        migrationBuilder.AddColumn<int>(
+            name: "SecurityVersion",
+            table: "User",
+            type: "int",
+            nullable: true);
+
+        migrationBuilder.AddColumn<string>(
+            name: "SignedPublicKey",
+            table: "User",
+            type: "longtext",
+            nullable: true)
+            .Annotation("MySql:CharSet", "utf8mb4");
+
+        migrationBuilder.CreateTable(
+            name: "UserSignatureKeyPair",
+            columns: table => new
+            {
+                Id = table.Column<Guid>(type: "char(36)", nullable: false, collation: "ascii_general_ci"),
+                UserId = table.Column<Guid>(type: "char(36)", nullable: false, collation: "ascii_general_ci"),
+                SignatureAlgorithm = table.Column<byte>(type: "tinyint unsigned", nullable: false),
+                VerifyingKey = table.Column<string>(type: "longtext", nullable: false)
+                    .Annotation("MySql:CharSet", "utf8mb4"),
+                SigningKey = table.Column<string>(type: "longtext", nullable: false)
+                    .Annotation("MySql:CharSet", "utf8mb4"),
+                CreationDate = table.Column<DateTime>(type: "datetime(6)", nullable: false),
+                RevisionDate = table.Column<DateTime>(type: "datetime(6)", nullable: false)
+            },
+            constraints: table =>
+            {
+                table.PrimaryKey("PK_UserSignatureKeyPair", x => x.Id);
+                table.ForeignKey(
+                    name: "FK_UserSignatureKeyPair_User_UserId",
+                    column: x => x.UserId,
+                    principalTable: "User",
+                    principalColumn: "Id",
+                    onDelete: ReferentialAction.Cascade);
+            })
+            .Annotation("MySql:CharSet", "utf8mb4");
+
+        migrationBuilder.CreateIndex(
+            name: "IX_UserSignatureKeyPair_UserId",
+            table: "UserSignatureKeyPair",
+            column: "UserId",
+            unique: true);
+    }
+
+    /// <inheritdoc />
+    protected override void Down(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.DropTable(
+            name: "UserSignatureKeyPair");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityState",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityVersion",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SignedPublicKey",
+            table: "User");
+    }
+}

util/MySqlMigrations/Migrations/DatabaseContextModelSnapshot.cs

@@ -1873,6 +1873,15 @@ namespace Bit.MySqlMigrations.Migrations
                         .HasMaxLength(50)
                         .HasColumnType("varchar(50)");
 
+                    b.Property<string>("SecurityState")
+                        .HasColumnType("longtext");
+
+                    b.Property<int?>("SecurityVersion")
+                        .HasColumnType("int");
+
+                    b.Property<string>("SignedPublicKey")
+                        .HasColumnType("longtext");
+
                     b.Property<long?>("Storage")
                         .HasColumnType("bigint");
 
@@ -1901,6 +1910,40 @@ namespace Bit.MySqlMigrations.Migrations
                     b.ToTable("User", (string)null);
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.Property<Guid>("Id")
+                        .HasColumnType("char(36)");
+
+                    b.Property<DateTime>("CreationDate")
+                        .HasColumnType("datetime(6)");
+
+                    b.Property<DateTime>("RevisionDate")
+                        .HasColumnType("datetime(6)");
+
+                    b.Property<byte>("SignatureAlgorithm")
+                        .HasColumnType("tinyint unsigned");
+
+                    b.Property<string>("SigningKey")
+                        .IsRequired()
+                        .HasColumnType("longtext");
+
+                    b.Property<Guid>("UserId")
+                        .HasColumnType("char(36)");
+
+                    b.Property<string>("VerifyingKey")
+                        .IsRequired()
+                        .HasColumnType("longtext");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("UserId")
+                        .IsUnique()
+                        .HasAnnotation("SqlServer:Clustered", false);
+
+                    b.ToTable("UserSignatureKeyPair", (string)null);
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.Property<Guid>("Id")
@@ -2948,6 +2991,17 @@ namespace Bit.MySqlMigrations.Migrations
                     b.Navigation("User");
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.HasOne("Bit.Infrastructure.EntityFramework.Models.User", "User")
+                        .WithMany()
+                        .HasForeignKey("UserId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("User");
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.HasOne("Bit.Infrastructure.EntityFramework.AdminConsole.Models.Organization", "Organization")

util/PostgresMigrations/Migrations/20251013083502_UserCryptoV2.cs

@@ -0,0 +1,79 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace Bit.PostgresMigrations.Migrations;
+
+/// <inheritdoc />
+public partial class UserCryptoV2 : Migration
+{
+    /// <inheritdoc />
+    protected override void Up(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.AddColumn<string>(
+            name: "SecurityState",
+            table: "User",
+            type: "text",
+            nullable: true);
+
+        migrationBuilder.AddColumn<int>(
+            name: "SecurityVersion",
+            table: "User",
+            type: "integer",
+            nullable: true);
+
+        migrationBuilder.AddColumn<string>(
+            name: "SignedPublicKey",
+            table: "User",
+            type: "text",
+            nullable: true);
+
+        migrationBuilder.CreateTable(
+            name: "UserSignatureKeyPair",
+            columns: table => new
+            {
+                Id = table.Column<Guid>(type: "uuid", nullable: false),
+                UserId = table.Column<Guid>(type: "uuid", nullable: false),
+                SignatureAlgorithm = table.Column<byte>(type: "smallint", nullable: false),
+                VerifyingKey = table.Column<string>(type: "text", nullable: false),
+                SigningKey = table.Column<string>(type: "text", nullable: false),
+                CreationDate = table.Column<DateTime>(type: "timestamp with time zone", nullable: false),
+                RevisionDate = table.Column<DateTime>(type: "timestamp with time zone", nullable: false)
+            },
+            constraints: table =>
+            {
+                table.PrimaryKey("PK_UserSignatureKeyPair", x => x.Id);
+                table.ForeignKey(
+                    name: "FK_UserSignatureKeyPair_User_UserId",
+                    column: x => x.UserId,
+                    principalTable: "User",
+                    principalColumn: "Id",
+                    onDelete: ReferentialAction.Cascade);
+            });
+
+        migrationBuilder.CreateIndex(
+            name: "IX_UserSignatureKeyPair_UserId",
+            table: "UserSignatureKeyPair",
+            column: "UserId",
+            unique: true);
+    }
+
+    /// <inheritdoc />
+    protected override void Down(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.DropTable(
+            name: "UserSignatureKeyPair");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityState",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityVersion",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SignedPublicKey",
+            table: "User");
+    }
+}

util/PostgresMigrations/Migrations/DatabaseContextModelSnapshot.cs

@@ -1879,6 +1879,15 @@ namespace Bit.PostgresMigrations.Migrations
                         .HasMaxLength(50)
                         .HasColumnType("character varying(50)");
 
+                    b.Property<string>("SecurityState")
+                        .HasColumnType("text");
+
+                    b.Property<int?>("SecurityVersion")
+                        .HasColumnType("integer");
+
+                    b.Property<string>("SignedPublicKey")
+                        .HasColumnType("text");
+
                     b.Property<long?>("Storage")
                         .HasColumnType("bigint");
 
@@ -1907,6 +1916,40 @@ namespace Bit.PostgresMigrations.Migrations
                     b.ToTable("User", (string)null);
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.Property<Guid>("Id")
+                        .HasColumnType("uuid");
+
+                    b.Property<DateTime>("CreationDate")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<DateTime>("RevisionDate")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<byte>("SignatureAlgorithm")
+                        .HasColumnType("smallint");
+
+                    b.Property<string>("SigningKey")
+                        .IsRequired()
+                        .HasColumnType("text");
+
+                    b.Property<Guid>("UserId")
+                        .HasColumnType("uuid");
+
+                    b.Property<string>("VerifyingKey")
+                        .IsRequired()
+                        .HasColumnType("text");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("UserId")
+                        .IsUnique()
+                        .HasAnnotation("SqlServer:Clustered", false);
+
+                    b.ToTable("UserSignatureKeyPair", (string)null);
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.Property<Guid>("Id")
@@ -2954,6 +2997,17 @@ namespace Bit.PostgresMigrations.Migrations
                     b.Navigation("User");
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.HasOne("Bit.Infrastructure.EntityFramework.Models.User", "User")
+                        .WithMany()
+                        .HasForeignKey("UserId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("User");
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.HasOne("Bit.Infrastructure.EntityFramework.AdminConsole.Models.Organization", "Organization")

util/SqliteMigrations/Migrations/20251013083514_UserCryptoV2.cs

@@ -0,0 +1,79 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace Bit.SqliteMigrations.Migrations;
+
+/// <inheritdoc />
+public partial class UserCryptoV2 : Migration
+{
+    /// <inheritdoc />
+    protected override void Up(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.AddColumn<string>(
+            name: "SecurityState",
+            table: "User",
+            type: "TEXT",
+            nullable: true);
+
+        migrationBuilder.AddColumn<int>(
+            name: "SecurityVersion",
+            table: "User",
+            type: "INTEGER",
+            nullable: true);
+
+        migrationBuilder.AddColumn<string>(
+            name: "SignedPublicKey",
+            table: "User",
+            type: "TEXT",
+            nullable: true);
+
+        migrationBuilder.CreateTable(
+            name: "UserSignatureKeyPair",
+            columns: table => new
+            {
+                Id = table.Column<Guid>(type: "TEXT", nullable: false),
+                UserId = table.Column<Guid>(type: "TEXT", nullable: false),
+                SignatureAlgorithm = table.Column<byte>(type: "INTEGER", nullable: false),
+                VerifyingKey = table.Column<string>(type: "TEXT", nullable: false),
+                SigningKey = table.Column<string>(type: "TEXT", nullable: false),
+                CreationDate = table.Column<DateTime>(type: "TEXT", nullable: false),
+                RevisionDate = table.Column<DateTime>(type: "TEXT", nullable: false)
+            },
+            constraints: table =>
+            {
+                table.PrimaryKey("PK_UserSignatureKeyPair", x => x.Id);
+                table.ForeignKey(
+                    name: "FK_UserSignatureKeyPair_User_UserId",
+                    column: x => x.UserId,
+                    principalTable: "User",
+                    principalColumn: "Id",
+                    onDelete: ReferentialAction.Cascade);
+            });
+
+        migrationBuilder.CreateIndex(
+            name: "IX_UserSignatureKeyPair_UserId",
+            table: "UserSignatureKeyPair",
+            column: "UserId",
+            unique: true);
+    }
+
+    /// <inheritdoc />
+    protected override void Down(MigrationBuilder migrationBuilder)
+    {
+        migrationBuilder.DropTable(
+            name: "UserSignatureKeyPair");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityState",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SecurityVersion",
+            table: "User");
+
+        migrationBuilder.DropColumn(
+            name: "SignedPublicKey",
+            table: "User");
+    }
+}

util/SqliteMigrations/Migrations/DatabaseContextModelSnapshot.cs

@@ -1862,6 +1862,15 @@ namespace Bit.SqliteMigrations.Migrations
                         .HasMaxLength(50)
                         .HasColumnType("TEXT");
 
+                    b.Property<string>("SecurityState")
+                        .HasColumnType("TEXT");
+
+                    b.Property<int?>("SecurityVersion")
+                        .HasColumnType("INTEGER");
+
+                    b.Property<string>("SignedPublicKey")
+                        .HasColumnType("TEXT");
+
                     b.Property<long?>("Storage")
                         .HasColumnType("INTEGER");
 
@@ -1890,6 +1899,40 @@ namespace Bit.SqliteMigrations.Migrations
                     b.ToTable("User", (string)null);
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.Property<Guid>("Id")
+                        .HasColumnType("TEXT");
+
+                    b.Property<DateTime>("CreationDate")
+                        .HasColumnType("TEXT");
+
+                    b.Property<DateTime>("RevisionDate")
+                        .HasColumnType("TEXT");
+
+                    b.Property<byte>("SignatureAlgorithm")
+                        .HasColumnType("INTEGER");
+
+                    b.Property<string>("SigningKey")
+                        .IsRequired()
+                        .HasColumnType("TEXT");
+
+                    b.Property<Guid>("UserId")
+                        .HasColumnType("TEXT");
+
+                    b.Property<string>("VerifyingKey")
+                        .IsRequired()
+                        .HasColumnType("TEXT");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("UserId")
+                        .IsUnique()
+                        .HasAnnotation("SqlServer:Clustered", false);
+
+                    b.ToTable("UserSignatureKeyPair", (string)null);
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.Property<Guid>("Id")
@@ -2937,6 +2980,17 @@ namespace Bit.SqliteMigrations.Migrations
                     b.Navigation("User");
                 });
 
+            modelBuilder.Entity("Bit.Infrastructure.EntityFramework.Models.UserSignatureKeyPair", b =>
+                {
+                    b.HasOne("Bit.Infrastructure.EntityFramework.Models.User", "User")
+                        .WithMany()
+                        .HasForeignKey("UserId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("User");
+                });
+
             modelBuilder.Entity("Bit.Infrastructure.EntityFramework.NotificationCenter.Models.Notification", b =>
                 {
                     b.HasOne("Bit.Infrastructure.EntityFramework.AdminConsole.Models.Organization", "Organization")