[PM-27280] Support v2 encryption on key-connector signups (#6712)

* account v2 registration for key connector

* use new user repository functions

* test coverage

* integration test coverage

* documentation

* code review

* missing test coverage

* fix failing test

* failing test

* incorrect ticket number

* moved back request model to Api, created dedicated data class in Core

* sql stored procedure type mismatch, simplification

* key connector authorization handler

src/Api/KeyManagement/Controllers/AccountsKeyManagementController.cs

@@ -47,6 +47,7 @@ public class AccountsKeyManagementController : Controller
         _webauthnKeyValidator;
     private readonly IRotationValidator<IEnumerable<OtherDeviceKeysUpdateRequestModel>, IEnumerable<Device>> _deviceValidator;
     private readonly IKeyConnectorConfirmationDetailsQuery _keyConnectorConfirmationDetailsQuery;
+    private readonly ISetKeyConnectorKeyCommand _setKeyConnectorKeyCommand;
 
     public AccountsKeyManagementController(IUserService userService,
         IFeatureService featureService,
@@ -62,8 +63,10 @@ public class AccountsKeyManagementController : Controller
             emergencyAccessValidator,
         IRotationValidator<IEnumerable<ResetPasswordWithOrgIdRequestModel>, IReadOnlyList<OrganizationUser>>
             organizationUserValidator,
-        IRotationValidator<IEnumerable<WebAuthnLoginRotateKeyRequestModel>, IEnumerable<WebAuthnLoginRotateKeyData>> webAuthnKeyValidator,
-        IRotationValidator<IEnumerable<OtherDeviceKeysUpdateRequestModel>, IEnumerable<Device>> deviceValidator)
+        IRotationValidator<IEnumerable<WebAuthnLoginRotateKeyRequestModel>, IEnumerable<WebAuthnLoginRotateKeyData>>
+            webAuthnKeyValidator,
+        IRotationValidator<IEnumerable<OtherDeviceKeysUpdateRequestModel>, IEnumerable<Device>> deviceValidator,
+        ISetKeyConnectorKeyCommand setKeyConnectorKeyCommand)
     {
         _userService = userService;
         _featureService = featureService;
@@ -79,6 +82,7 @@ public class AccountsKeyManagementController : Controller
         _webauthnKeyValidator = webAuthnKeyValidator;
         _deviceValidator = deviceValidator;
         _keyConnectorConfirmationDetailsQuery = keyConnectorConfirmationDetailsQuery;
+        _setKeyConnectorKeyCommand = setKeyConnectorKeyCommand;
     }
 
     [HttpPost("key-management/regenerate-keys")]
@@ -146,18 +150,28 @@ public class AccountsKeyManagementController : Controller
             throw new UnauthorizedAccessException();
         }
 
-        var result = await _userService.SetKeyConnectorKeyAsync(model.ToUser(user), model.Key, model.OrgIdentifier);
-        if (result.Succeeded)
+        if (model.IsV2Request())
         {
-            return;
+            // V2 account registration
+            await _setKeyConnectorKeyCommand.SetKeyConnectorKeyForUserAsync(user, model.ToKeyConnectorKeysData());
         }
-
-        foreach (var error in result.Errors)
+        else
         {
-            ModelState.AddModelError(string.Empty, error.Description);
-        }
+            // V1 account registration
+            // TODO removed with https://bitwarden.atlassian.net/browse/PM-27328
+            var result = await _userService.SetKeyConnectorKeyAsync(model.ToUser(user), model.Key, model.OrgIdentifier);
+            if (result.Succeeded)
+            {
+                return;
+            }
 
-        throw new BadRequestException(ModelState);
+            foreach (var error in result.Errors)
+            {
+                ModelState.AddModelError(string.Empty, error.Description);
+            }
+
+            throw new BadRequestException(ModelState);
+        }
     }
 
     [HttpPost("convert-to-key-connector")]

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

@@ -1,36 +1,112 @@
-// FIXME: Update this file to be null safe and then delete the line below
-#nullable disable
-
-using System.ComponentModel.DataAnnotations;
+using System.ComponentModel.DataAnnotations;
 using Bit.Core.Auth.Models.Api.Request.Accounts;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
+using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Models.Api.Request;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.Utilities;
 
 namespace Bit.Api.KeyManagement.Models.Requests;
 
-public class SetKeyConnectorKeyRequestModel
+public class SetKeyConnectorKeyRequestModel : IValidatableObject
 {
-    [Required]
-    public string Key { get; set; }
-    [Required]
-    public KeysRequestModel Keys { get; set; }
-    [Required]
-    public KdfType Kdf { get; set; }
-    [Required]
-    public int KdfIterations { get; set; }
-    public int? KdfMemory { get; set; }
-    public int? KdfParallelism { get; set; }
-    [Required]
-    public string OrgIdentifier { get; set; }
+    // TODO will be removed with https://bitwarden.atlassian.net/browse/PM-27328
+    [Obsolete("Use KeyConnectorKeyWrappedUserKey instead")]
+    public string? Key { get; set; }
 
+    [Obsolete("Use AccountKeys instead")]
+    public KeysRequestModel? Keys { get; set; }
+    [Obsolete("Not used anymore")]
+    public KdfType? Kdf { get; set; }
+    [Obsolete("Not used anymore")]
+    public int? KdfIterations { get; set; }
+    [Obsolete("Not used anymore")]
+    public int? KdfMemory { get; set; }
+    [Obsolete("Not used anymore")]
+    public int? KdfParallelism { get; set; }
+
+    [EncryptedString]
+    public string? KeyConnectorKeyWrappedUserKey { get; set; }
+    public AccountKeysRequestModel? AccountKeys { get; set; }
+
+    [Required]
+    public required string OrgIdentifier { get; init; }
+
+    public IEnumerable<ValidationResult> Validate(ValidationContext validationContext)
+    {
+        if (IsV2Request())
+        {
+            // V2 registration
+            yield break;
+        }
+
+        // V1 registration
+        // TODO removed with https://bitwarden.atlassian.net/browse/PM-27328
+        if (string.IsNullOrEmpty(Key))
+        {
+            yield return new ValidationResult("Key must be supplied.");
+        }
+
+        if (Keys == null)
+        {
+            yield return new ValidationResult("Keys must be supplied.");
+        }
+
+        if (Kdf == null)
+        {
+            yield return new ValidationResult("Kdf must be supplied.");
+        }
+
+        if (KdfIterations == null)
+        {
+            yield return new ValidationResult("KdfIterations must be supplied.");
+        }
+
+        if (Kdf == KdfType.Argon2id)
+        {
+            if (KdfMemory == null)
+            {
+                yield return new ValidationResult("KdfMemory must be supplied when Kdf is Argon2id.");
+            }
+
+            if (KdfParallelism == null)
+            {
+                yield return new ValidationResult("KdfParallelism must be supplied when Kdf is Argon2id.");
+            }
+        }
+    }
+
+    public bool IsV2Request()
+    {
+        return !string.IsNullOrEmpty(KeyConnectorKeyWrappedUserKey) && AccountKeys != null;
+    }
+
+    // TODO removed with https://bitwarden.atlassian.net/browse/PM-27328
     public User ToUser(User existingUser)
     {
-        existingUser.Kdf = Kdf;
-        existingUser.KdfIterations = KdfIterations;
+        existingUser.Kdf = Kdf!.Value;
+        existingUser.KdfIterations = KdfIterations!.Value;
         existingUser.KdfMemory = KdfMemory;
         existingUser.KdfParallelism = KdfParallelism;
         existingUser.Key = Key;
-        Keys.ToUser(existingUser);
+        Keys!.ToUser(existingUser);
         return existingUser;
     }
+
+    public KeyConnectorKeysData ToKeyConnectorKeysData()
+    {
+        // TODO remove validation with https://bitwarden.atlassian.net/browse/PM-27328
+        if (string.IsNullOrEmpty(KeyConnectorKeyWrappedUserKey) || AccountKeys == null)
+        {
+            throw new BadRequestException("KeyConnectorKeyWrappedUserKey and AccountKeys must be supplied.");
+        }
+
+        return new KeyConnectorKeysData
+        {
+            KeyConnectorKeyWrappedUserKey = KeyConnectorKeyWrappedUserKey,
+            AccountKeys = AccountKeys,
+            OrgIdentifier = OrgIdentifier
+        };
+    }
 }

src/Core/Constants.cs

@@ -212,6 +212,7 @@ public static class FeatureFlagKeys
     public const string ConsolidatedSessionTimeoutComponent = "pm-26056-consolidated-session-timeout-component";
     public const string V2RegistrationTDEJIT = "pm-27279-v2-registration-tde-jit";
     public const string DataRecoveryTool = "pm-28813-data-recovery-tool";
+    public const string EnableAccountEncryptionV2KeyConnectorRegistration = "enable-account-encryption-v2-key-connector-registration";
 
     /* Mobile Team */
     public const string AndroidImportLoginsFlow = "import-logins-flow";

src/Core/KeyManagement/Authorization/KeyConnectorAuthorizationHandler.cs

@@ -0,0 +1,52 @@
+using Bit.Core.Context;
+using Bit.Core.Entities;
+using Bit.Core.Enums;
+using Microsoft.AspNetCore.Authorization;
+
+namespace Bit.Core.KeyManagement.Authorization;
+
+public class KeyConnectorAuthorizationHandler : AuthorizationHandler<KeyConnectorOperationsRequirement, User>
+{
+    private readonly ICurrentContext _currentContext;
+
+    public KeyConnectorAuthorizationHandler(ICurrentContext currentContext)
+    {
+        _currentContext = currentContext;
+    }
+
+    protected override Task HandleRequirementAsync(AuthorizationHandlerContext context,
+        KeyConnectorOperationsRequirement requirement,
+        User user)
+    {
+        var authorized = requirement switch
+        {
+            not null when requirement == KeyConnectorOperations.Use => CanUse(user),
+            _ => throw new ArgumentException("Unsupported operation requirement type provided.", nameof(requirement))
+        };
+
+        if (authorized)
+        {
+            context.Succeed(requirement);
+        }
+
+        return Task.CompletedTask;
+    }
+
+    private bool CanUse(User user)
+    {
+        // User cannot use Key Connector if they already use it
+        if (user.UsesKeyConnector)
+        {
+            return false;
+        }
+
+        // User cannot use Key Connector if they are an owner or admin of any organization
+        if (_currentContext.Organizations.Any(u =>
+                u.Type is OrganizationUserType.Owner or OrganizationUserType.Admin))
+        {
+            return false;
+        }
+
+        return true;
+    }
+}

src/Core/KeyManagement/Authorization/KeyConnectorOperations.cs

@@ -0,0 +1,16 @@
+using Microsoft.AspNetCore.Authorization.Infrastructure;
+
+namespace Bit.Core.KeyManagement.Authorization;
+
+public class KeyConnectorOperationsRequirement : OperationAuthorizationRequirement
+{
+    public KeyConnectorOperationsRequirement(string name)
+    {
+        Name = name;
+    }
+}
+
+public static class KeyConnectorOperations
+{
+    public static readonly KeyConnectorOperationsRequirement Use = new(nameof(Use));
+}

src/Core/KeyManagement/Commands/Interfaces/ISetKeyConnectorKeyCommand.cs

@@ -0,0 +1,13 @@
+using Bit.Core.Entities;
+using Bit.Core.KeyManagement.Models.Data;
+
+namespace Bit.Core.KeyManagement.Commands.Interfaces;
+
+/// <summary>
+/// Creates the user key and account cryptographic state for a new user registering
+/// with Key Connector SSO configuration.
+/// </summary>
+public interface ISetKeyConnectorKeyCommand
+{
+    Task SetKeyConnectorKeyForUserAsync(User user, KeyConnectorKeysData keyConnectorKeysData);
+}

src/Core/KeyManagement/Commands/SetKeyConnectorKeyCommand.cs

@@ -0,0 +1,60 @@
+using Bit.Core.Context;
+using Bit.Core.Entities;
+using Bit.Core.Enums;
+using Bit.Core.Exceptions;
+using Bit.Core.KeyManagement.Authorization;
+using Bit.Core.KeyManagement.Commands.Interfaces;
+using Bit.Core.KeyManagement.Models.Data;
+using Bit.Core.OrganizationFeatures.OrganizationUsers.Interfaces;
+using Bit.Core.Repositories;
+using Bit.Core.Services;
+using Microsoft.AspNetCore.Authorization;
+
+namespace Bit.Core.KeyManagement.Commands;
+
+public class SetKeyConnectorKeyCommand : ISetKeyConnectorKeyCommand
+{
+    private readonly IAuthorizationService _authorizationService;
+    private readonly ICurrentContext _currentContext;
+    private readonly IEventService _eventService;
+    private readonly IAcceptOrgUserCommand _acceptOrgUserCommand;
+    private readonly IUserService _userService;
+    private readonly IUserRepository _userRepository;
+
+    public SetKeyConnectorKeyCommand(
+        IAuthorizationService authorizationService,
+        ICurrentContext currentContext,
+        IEventService eventService,
+        IAcceptOrgUserCommand acceptOrgUserCommand,
+        IUserService userService,
+        IUserRepository userRepository)
+    {
+        _authorizationService = authorizationService;
+        _currentContext = currentContext;
+        _eventService = eventService;
+        _acceptOrgUserCommand = acceptOrgUserCommand;
+        _userService = userService;
+        _userRepository = userRepository;
+    }
+
+    public async Task SetKeyConnectorKeyForUserAsync(User user, KeyConnectorKeysData keyConnectorKeysData)
+    {
+        var authorizationResult = await _authorizationService.AuthorizeAsync(_currentContext.HttpContext.User, user,
+            KeyConnectorOperations.Use);
+        if (!authorizationResult.Succeeded)
+        {
+            throw new BadRequestException("Cannot use Key Connector");
+        }
+
+        var setKeyConnectorUserKeyTask =
+            _userRepository.SetKeyConnectorUserKey(user.Id, keyConnectorKeysData.KeyConnectorKeyWrappedUserKey);
+
+        await _userRepository.SetV2AccountCryptographicStateAsync(user.Id,
+            keyConnectorKeysData.AccountKeys.ToAccountKeysData(), [setKeyConnectorUserKeyTask]);
+
+        await _eventService.LogUserEventAsync(user.Id, EventType.User_MigratedKeyToKeyConnector);
+
+        await _acceptOrgUserCommand.AcceptOrgUserByOrgSsoIdAsync(keyConnectorKeysData.OrgIdentifier, user,
+            _userService);
+    }
+}

src/Core/KeyManagement/KeyManagementServiceCollectionExtensions.cs

@@ -1,9 +1,11 @@
-using Bit.Core.KeyManagement.Commands;
+using Bit.Core.KeyManagement.Authorization;
+using Bit.Core.KeyManagement.Commands;
 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.AspNetCore.Authorization;
 using Microsoft.Extensions.DependencyInjection;
 
 namespace Bit.Core.KeyManagement;
@@ -12,15 +14,22 @@ public static class KeyManagementServiceCollectionExtensions
 {
     public static void AddKeyManagementServices(this IServiceCollection services)
     {
+        services.AddKeyManagementAuthorizationHandlers();
         services.AddKeyManagementCommands();
         services.AddKeyManagementQueries();
         services.AddSendPasswordServices();
     }
 
+    private static void AddKeyManagementAuthorizationHandlers(this IServiceCollection services)
+    {
+        services.AddScoped<IAuthorizationHandler, KeyConnectorAuthorizationHandler>();
+    }
+
     private static void AddKeyManagementCommands(this IServiceCollection services)
     {
         services.AddScoped<IRegenerateUserAsymmetricKeysCommand, RegenerateUserAsymmetricKeysCommand>();
         services.AddScoped<IChangeKdfCommand, ChangeKdfCommand>();
+        services.AddScoped<ISetKeyConnectorKeyCommand, SetKeyConnectorKeyCommand>();
     }
 
     private static void AddKeyManagementQueries(this IServiceCollection services)

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

@@ -0,0 +1,12 @@
+using Bit.Core.KeyManagement.Models.Api.Request;
+
+namespace Bit.Core.KeyManagement.Models.Data;
+
+public class KeyConnectorKeysData
+{
+    public required string KeyConnectorKeyWrappedUserKey { get; set; }
+
+    public required AccountKeysRequestModel AccountKeys { get; set; }
+
+    public required string OrgIdentifier { get; init; }
+}

src/Core/Repositories/IUserRepository.cs

@@ -72,6 +72,8 @@ public interface IUserRepository : IRepository<User, Guid>
         UserAccountKeysData accountKeysData,
         IEnumerable<UpdateUserData>? updateUserDataActions = null);
     Task DeleteManyAsync(IEnumerable<User> users);
+
+    UpdateUserData SetKeyConnectorUserKey(Guid userId, string keyConnectorWrappedUserKey);
 }
 
 public delegate Task UpdateUserData(Microsoft.Data.SqlClient.SqlConnection? connection = null,

src/Core/Services/IUserService.cs

@@ -33,6 +33,8 @@ public interface IUserService
     Task<IdentityResult> ChangeEmailAsync(User user, string masterPassword, string newEmail, string newMasterPassword,
         string token, string key);
     Task<IdentityResult> ChangePasswordAsync(User user, string masterPassword, string newMasterPassword, string passwordHint, string key);
+    // TODO removed with https://bitwarden.atlassian.net/browse/PM-27328
+    [Obsolete("Use ISetKeyConnectorKeyCommand instead. This method will be removed in a future version.")]
     Task<IdentityResult> SetKeyConnectorKeyAsync(User user, string key, string orgIdentifier);
     Task<IdentityResult> ConvertToKeyConnectorAsync(User user);
     Task<IdentityResult> AdminResetPasswordAsync(OrganizationUserType type, Guid orgId, Guid id, string newMasterPassword, string key);

src/Core/Services/Implementations/UserService.cs

@@ -621,6 +621,7 @@ public class UserService : UserManager<User>, IUserService
         return IdentityResult.Failed(_identityErrorDescriber.PasswordMismatch());
     }
 
+    // TODO removed with https://bitwarden.atlassian.net/browse/PM-27328
     public async Task<IdentityResult> SetKeyConnectorKeyAsync(User user, string key, string orgIdentifier)
     {
         var identityResult = CheckCanUseKeyConnector(user);

src/Infrastructure.Dapper/Repositories/UserRepository.cs

@@ -3,6 +3,7 @@ using System.Text.Json;
 using Bit.Core;
 using Bit.Core.Billing.Premium.Models;
 using Bit.Core.Entities;
+using Bit.Core.Enums;
 using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.KeyManagement.UserKey;
 using Bit.Core.Models.Data;
@@ -401,6 +402,32 @@ public class UserRepository : Repository<User, Guid>, IUserRepository
         return result.SingleOrDefault();
     }
 
+    public UpdateUserData SetKeyConnectorUserKey(Guid userId, string keyConnectorWrappedUserKey)
+    {
+        return async (connection, transaction) =>
+        {
+            var timestamp = DateTime.UtcNow;
+
+            await connection!.ExecuteAsync(
+                "[dbo].[User_UpdateKeyConnectorUserKey]",
+                new
+                {
+                    Id = userId,
+                    Key = keyConnectorWrappedUserKey,
+                    // Key Connector does not use KDF, so we set some defaults
+                    Kdf = KdfType.Argon2id,
+                    KdfIterations = AuthConstants.ARGON2_ITERATIONS.Default,
+                    KdfMemory = AuthConstants.ARGON2_MEMORY.Default,
+                    KdfParallelism = AuthConstants.ARGON2_PARALLELISM.Default,
+                    UsesKeyConnector = true,
+                    RevisionDate = timestamp,
+                    AccountRevisionDate = timestamp
+                },
+                transaction: transaction,
+                commandType: CommandType.StoredProcedure);
+        };
+    }
+
     private async Task ProtectDataAndSaveAsync(User user, Func<Task> saveTask)
     {
         if (user == null)

src/Infrastructure.EntityFramework/Repositories/UserRepository.cs

@@ -1,5 +1,7 @@
 using AutoMapper;
+using Bit.Core;
 using Bit.Core.Billing.Premium.Models;
+using Bit.Core.Enums;
 using Bit.Core.KeyManagement.Models.Data;
 using Bit.Core.KeyManagement.UserKey;
 using Bit.Core.Models.Data;
@@ -479,6 +481,35 @@ public class UserRepository : Repository<Core.Entities.User, User, Guid>, IUserR
         }
     }
 
+    public UpdateUserData SetKeyConnectorUserKey(Guid userId, string keyConnectorWrappedUserKey)
+    {
+        return async (_, _) =>
+        {
+            using var scope = ServiceScopeFactory.CreateScope();
+            var dbContext = GetDatabaseContext(scope);
+
+            var userEntity = await dbContext.Users.FindAsync(userId);
+            if (userEntity == null)
+            {
+                throw new ArgumentException("User not found", nameof(userId));
+            }
+
+            var timestamp = DateTime.UtcNow;
+
+            userEntity.Key = keyConnectorWrappedUserKey;
+            // Key Connector does not use KDF, so we set some defaults
+            userEntity.Kdf = KdfType.Argon2id;
+            userEntity.KdfIterations = AuthConstants.ARGON2_ITERATIONS.Default;
+            userEntity.KdfMemory = AuthConstants.ARGON2_MEMORY.Default;
+            userEntity.KdfParallelism = AuthConstants.ARGON2_PARALLELISM.Default;
+            userEntity.UsesKeyConnector = true;
+            userEntity.RevisionDate = timestamp;
+            userEntity.AccountRevisionDate = timestamp;
+
+            await dbContext.SaveChangesAsync();
+        };
+    }
+
     private static void MigrateDefaultUserCollectionsToShared(DatabaseContext dbContext, IEnumerable<Guid> userIds)
     {
         var defaultCollections = (from c in dbContext.Collections

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

@@ -0,0 +1,28 @@
+CREATE PROCEDURE [dbo].[User_UpdateKeyConnectorUserKey]
+    @Id UNIQUEIDENTIFIER,
+    @Key VARCHAR(MAX),
+    @Kdf TINYINT,
+    @KdfIterations INT,
+    @KdfMemory INT,
+    @KdfParallelism INT,
+    @UsesKeyConnector BIT,
+    @RevisionDate DATETIME2(7),
+    @AccountRevisionDate DATETIME2(7)
+AS
+BEGIN
+    SET NOCOUNT ON
+
+    UPDATE
+        [dbo].[User]
+    SET
+        [Key] = @Key,
+        [Kdf] = @Kdf,
+        [KdfIterations] = @KdfIterations,
+        [KdfMemory] = @KdfMemory,
+        [KdfParallelism] = @KdfParallelism,
+        [UsesKeyConnector] = @UsesKeyConnector,
+        [RevisionDate] = @RevisionDate,
+        [AccountRevisionDate] = @AccountRevisionDate
+    WHERE
+        [Id] = @Id
+END