[PM-2289] [PM-2293] TDE Login with device Admin Request (#2642)

* [PM-2297] Add DecryptUserKeyWithDeviceKey method

* [PM-2297] Add methods to DeviceTrustCryptoService update decryption options model

* [PM-2297] Update account decryption options model

* [PM-2297] Fix TrustedDeviceOption and DeviceResponse model. Change StateService device key get set to have default user id

* [PM-2297] Update navigation to decryption options

* [PM-2297] Add missing action navigations to iOS extensions

* [PM-2297] Fix trust device bug/typo

* [PM-2297] Fix model bug

* [PM-2297] Fix state var crash

* [PM-2297] Add trust device login logic to auth service

* [PM-2297] Refactor auth service key connector code

* [PM-2297] Remove reconciledOptions for deviceKey in state service

* [PM-2297] Remove unnecessary user id params

src/App/Pages/Accounts/LockPage.xaml

@@ -46,7 +46,7 @@
                     <StackLayout StyleClass="box">
                         <Grid
                             StyleClass="box-row"
-                            IsVisible="{Binding PinLock}"
+                            IsVisible="{Binding PinEnabled}"
                             Padding="0, 10, 0, 0">
                             <Grid.RowDefinitions>
                                 <RowDefinition Height="Auto" />
@@ -89,7 +89,7 @@
                         <Grid
                             x:Name="_passwordGrid"
                             StyleClass="box-row"
-                            IsVisible="{Binding PinLock, Converter={StaticResource inverseBool}}"
+                            IsVisible="{Binding PinEnabled, Converter={StaticResource inverseBool}}"
                             Padding="0, 10, 0, 0">
                             <Grid.RowDefinitions>
                                 <RowDefinition Height="Auto" />

src/App/Pages/Accounts/LockPage.xaml.cs

@@ -44,7 +44,7 @@ namespace Bit.App.Pages
         {
             get
             {
-                if (_vm?.PinLock ?? false)
+                if (_vm?.PinEnabled ?? false)
                 {
                     return _pin;
                 }
@@ -54,7 +54,7 @@ namespace Bit.App.Pages
 
         public async Task PromptBiometricAfterResumeAsync()
         {
-            if (_vm.BiometricLock)
+            if (_vm.BiometricEnabled)
             {
                 await Task.Delay(500);
                 if (!_promptedAfterResume)
@@ -91,13 +91,13 @@ namespace Bit.App.Pages
 
             _vm.FocusSecretEntry += PerformFocusSecretEntry;
 
-            if (!_vm.BiometricLock)
+            if (!_vm.BiometricEnabled)
             {
                 RequestFocus(SecretEntry);
             }
             else
             {
-                if (_vm.UsingKeyConnector && !_vm.PinLock)
+                if (_vm.UsingKeyConnector && !_vm.PinEnabled)
                 {
                     _passwordGrid.IsVisible = false;
                     _unlockButton.IsVisible = false;

src/App/Pages/Accounts/LockPageViewModel.cs

@@ -33,21 +33,21 @@ namespace Bit.App.Pages
         private readonly WeakEventManager<int?> _secretEntryFocusWeakEventManager = new WeakEventManager<int?>();
         private readonly IPolicyService _policyService;
         private readonly IPasswordGenerationService _passwordGenerationService;
-
+        private IDeviceTrustCryptoService _deviceTrustCryptoService;
+        private readonly ISyncService _syncService;
         private string _email;
         private string _masterPassword;
         private string _pin;
         private bool _showPassword;
-        private bool _pinLock;
+        private PinLockEnum _pinStatus;
-        private bool _biometricLock;
+        private bool _pinEnabled;
+        private bool _biometricEnabled;
         private bool _biometricIntegrityValid = true;
         private bool _biometricButtonVisible;
         private bool _usingKeyConnector;
         private string _biometricButtonText;
         private string _loggedInAsText;
         private string _lockedVerifyText;
-        private bool _isPinProtected;
-        private bool _isPinProtectedWithKey;
 
         public LockPageViewModel()
         {
@@ -65,6 +65,8 @@ namespace Bit.App.Pages
             _watchDeviceService = ServiceContainer.Resolve<IWatchDeviceService>();
             _policyService = ServiceContainer.Resolve<IPolicyService>();
             _passwordGenerationService = ServiceContainer.Resolve<IPasswordGenerationService>();
+            _deviceTrustCryptoService = ServiceContainer.Resolve<IDeviceTrustCryptoService>();
+            _syncService = ServiceContainer.Resolve<ISyncService>();
 
             PageTitle = AppResources.VerifyMasterPassword;
             TogglePasswordCommand = new Command(TogglePassword);
@@ -100,10 +102,10 @@ namespace Bit.App.Pages
                 });
         }
 
-        public bool PinLock
+        public bool PinEnabled
         {
-            get => _pinLock;
+            get => _pinEnabled;
-            set => SetProperty(ref _pinLock, value);
+            set => SetProperty(ref _pinEnabled, value);
         }
 
         public bool UsingKeyConnector
@@ -111,10 +113,10 @@ namespace Bit.App.Pages
             get => _usingKeyConnector;
         }
 
-        public bool BiometricLock
+        public bool BiometricEnabled
         {
-            get => _biometricLock;
+            get => _biometricEnabled;
-            set => SetProperty(ref _biometricLock, value);
+            set => SetProperty(ref _biometricEnabled, value);
         }
 
         public bool BiometricIntegrityValid
@@ -162,14 +164,18 @@ namespace Bit.App.Pages
 
         public async Task InitAsync()
         {
-            (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
+            _pinStatus = await _vaultTimeoutService.IsPinLockSetAsync();
-            PinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
+
-                      _isPinProtectedWithKey;
+            var ephemeralPinSet = await _stateService.GetUserKeyPinEphemeralAsync()
-            BiometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() && await _cryptoService.HasKeyAsync();
+                ?? await _stateService.GetPinProtectedKeyAsync();
+            PinEnabled = (_pinStatus == PinLockEnum.Transient && ephemeralPinSet != null) ||
+                      _pinStatus == PinLockEnum.Persistent;
+
+            BiometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync() && await _cryptoService.HasEncryptedUserKeyAsync();
 
             // Users with key connector and without biometric or pin has no MP to unlock with
             _usingKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-            if (_usingKeyConnector && !(BiometricLock || PinLock))
+            if (_usingKeyConnector && !(BiometricEnabled || PinEnabled))
             {
                 await _vaultTimeoutService.LogOutAsync();
                 return;
@@ -188,7 +194,7 @@ namespace Bit.App.Pages
             }
             var webVaultHostname = CoreHelpers.GetHostname(webVault);
             LoggedInAsText = string.Format(AppResources.LoggedInAsOn, _email, webVaultHostname);
-            if (PinLock)
+            if (PinEnabled)
             {
                 PageTitle = AppResources.VerifyPIN;
                 LockedVerifyText = AppResources.VaultLockedPIN;
@@ -207,7 +213,7 @@ namespace Bit.App.Pages
                 }
             }
 
-            if (BiometricLock)
+            if (BiometricEnabled)
             {
                 BiometricIntegrityValid = await _platformUtilsService.IsBiometricIntegrityValidAsync();
                 if (!_biometricIntegrityValid)
@@ -229,14 +235,14 @@ namespace Bit.App.Pages
 
         public async Task SubmitAsync()
         {
-            if (PinLock && string.IsNullOrWhiteSpace(Pin))
+            if (PinEnabled && string.IsNullOrWhiteSpace(Pin))
             {
                 await Page.DisplayAlert(AppResources.AnErrorHasOccurred,
                     string.Format(AppResources.ValidationFieldRequired, AppResources.PIN),
                     AppResources.Ok);
                 return;
             }
-            if (!PinLock && string.IsNullOrWhiteSpace(MasterPassword))
+            if (!PinEnabled && string.IsNullOrWhiteSpace(MasterPassword))
             {
                 await Page.DisplayAlert(AppResources.AnErrorHasOccurred,
                     string.Format(AppResources.ValidationFieldRequired, AppResources.MasterPassword),
@@ -247,34 +253,54 @@ namespace Bit.App.Pages
             ShowPassword = false;
             var kdfConfig = await _stateService.GetActiveUserCustomDataAsync(a => new KdfConfig(a?.Profile));
 
-            if (PinLock)
+            if (PinEnabled)
             {
                 var failed = true;
                 try
                 {
-                    if (_isPinProtected)
+                    EncString userKeyPin = null;
+                    EncString oldPinProtected = null;
+                    if (_pinStatus == PinLockEnum.Persistent)
                     {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(Pin, _email,
+                        userKeyPin = await _stateService.GetUserKeyPinAsync();
+                        var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
+                        oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
+                    }
+                    else if (_pinStatus == PinLockEnum.Transient)
+                    {
+                        userKeyPin = await _stateService.GetUserKeyPinEphemeralAsync();
+                        oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                    }
+
+                    UserKey userKey;
+                    if (oldPinProtected != null)
+                    {
+                        userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                            _pinStatus == PinLockEnum.Transient,
+                            Pin,
+                            _email,
                             kdfConfig,
-                            await _stateService.GetPinProtectedKeyAsync());
+                            oldPinProtected
-                        var encKey = await _cryptoService.GetEncKeyAsync(key);
+                        );
+                    }
+                    else
+                    {
+                        userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
+                            Pin,
+                            _email,
+                            kdfConfig,
+                            userKeyPin
+                        );
+                    }
+
                     var protectedPin = await _stateService.GetProtectedPinAsync();
-                        var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
+                    var decryptedPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), userKey);
-                        failed = decPin != Pin;
+                    failed = decryptedPin != Pin;
                     if (!failed)
                     {
                         Pin = string.Empty;
                         await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                            await SetKeyAndContinueAsync(key);
+                        await SetKeyAndContinueAsync(userKey);
-                        }
-                    }
-                    else
-                    {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(Pin, _email, kdfConfig);
-                        failed = false;
-                        Pin = string.Empty;
-                        await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                        await SetKeyAndContinueAsync(key);
                     }
                 }
                 catch
@@ -295,19 +321,21 @@ namespace Bit.App.Pages
             }
             else
             {
-                var key = await _cryptoService.MakeKeyAsync(MasterPassword, _email, kdfConfig);
+                var masterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, _email, kdfConfig);
-                var storedKeyHash = await _cryptoService.GetKeyHashAsync();
+                var storedKeyHash = await _cryptoService.GetPasswordHashAsync();
                 var passwordValid = false;
                 MasterPasswordPolicyOptions enforcedMasterPasswordOptions = null;
 
                 if (storedKeyHash != null)
                 {
-                    passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(MasterPassword, key);
+                    // Offline unlock possible
+                    passwordValid = await _cryptoService.CompareAndUpdatePasswordHashAsync(MasterPassword, masterKey);
                 }
                 else
                 {
+                    // Online unlock required
                     await _deviceActionService.ShowLoadingAsync(AppResources.Loading);
-                    var keyHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.ServerAuthorization);
+                    var keyHash = await _cryptoService.HashPasswordAsync(MasterPassword, masterKey, HashPurpose.ServerAuthorization);
                     var request = new PasswordVerificationRequest();
                     request.MasterPasswordHash = keyHash;
 
@@ -316,8 +344,8 @@ namespace Bit.App.Pages
                         var response = await _apiService.PostAccountVerifyPasswordAsync(request);
                         enforcedMasterPasswordOptions = response.MasterPasswordPolicy;
                         passwordValid = true;
-                        var localKeyHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.LocalAuthorization);
+                        var localKeyHash = await _cryptoService.HashPasswordAsync(MasterPassword, masterKey, HashPurpose.LocalAuthorization);
-                        await _cryptoService.SetKeyHashAsync(localKeyHash);
+                        await _cryptoService.SetPasswordHashAsync(localKeyHash);
                     }
                     catch (Exception e)
                     {
@@ -327,15 +355,6 @@ namespace Bit.App.Pages
                 }
                 if (passwordValid)
                 {
-                    if (_isPinProtected)
-                    {
-                        var protectedPin = await _stateService.GetProtectedPinAsync();
-                        var encKey = await _cryptoService.GetEncKeyAsync(key);
-                        var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                        var pinKey = await _cryptoService.MakePinKeyAysnc(decPin, _email, kdfConfig);
-                        await _stateService.SetPinProtectedKeyAsync(await _cryptoService.EncryptAsync(key.Key, pinKey));
-                    }
-
                     if (await RequirePasswordChangeAsync(enforcedMasterPasswordOptions))
                     {
                         // Save the ForcePasswordResetReason to force a password reset after unlock
@@ -345,10 +364,13 @@ namespace Bit.App.Pages
 
                     MasterPassword = string.Empty;
                     await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                    await SetKeyAndContinueAsync(key);
+
+                    var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                    await _cryptoService.SetMasterKeyAsync(masterKey);
+                    await SetKeyAndContinueAsync(userKey);
 
                     // Re-enable biometrics
-                    if (BiometricLock & !BiometricIntegrityValid)
+                    if (BiometricEnabled & !BiometricIntegrityValid)
                     {
                         await _biometricService.SetupBiometricAsync();
                     }
@@ -425,7 +447,7 @@ namespace Bit.App.Pages
         public void TogglePassword()
         {
             ShowPassword = !ShowPassword;
-            var secret = PinLock ? Pin : MasterPassword;
+            var secret = PinEnabled ? Pin : MasterPassword;
             _secretEntryFocusWeakEventManager.RaiseEvent(string.IsNullOrEmpty(secret) ? 0 : secret.Length, nameof(FocusSecretEntry));
         }
 
@@ -433,12 +455,12 @@ namespace Bit.App.Pages
         {
             BiometricIntegrityValid = await _platformUtilsService.IsBiometricIntegrityValidAsync();
             BiometricButtonVisible = BiometricIntegrityValid;
-            if (!BiometricLock || !BiometricIntegrityValid)
+            if (!BiometricEnabled || !BiometricIntegrityValid)
             {
                 return;
             }
             var success = await _platformUtilsService.AuthenticateBiometricAsync(null,
-                PinLock ? AppResources.PIN : AppResources.MasterPassword,
+                PinEnabled ? AppResources.PIN : AppResources.MasterPassword,
                 () => _secretEntryFocusWeakEventManager.RaiseEvent((int?)null, nameof(FocusSecretEntry)));
             await _stateService.SetBiometricLockedAsync(!success);
             if (success)
@@ -447,18 +469,20 @@ namespace Bit.App.Pages
             }
         }
 
-        private async Task SetKeyAndContinueAsync(SymmetricCryptoKey key)
+        private async Task SetKeyAndContinueAsync(UserKey key)
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
-                await _cryptoService.SetKeyAsync(key);
+                await _cryptoService.SetUserKeyAsync(key);
             }
+            await _deviceTrustCryptoService.TrustDeviceIfNeededAsync();
             await DoContinueAsync();
         }
 
         private async Task DoContinueAsync()
         {
+            _syncService.FullSyncAsync(false).FireAndForget();
             await _stateService.SetBiometricLockedAsync(false);
             _watchDeviceService.SyncDataToWatchAsync().FireAndForget();
             _messagingService.Send("unlocked");

src/App/Pages/Accounts/LoginApproveDevicePage.xaml

@@ -0,0 +1,76 @@
+<?xml version="1.0" encoding="UTF-8" ?>
+<pages:BaseContentPage 
+    xmlns="http://xamarin.com/schemas/2014/forms"
+    xmlns:x="http://schemas.microsoft.com/winfx/2009/xaml"
+    x:Class="Bit.App.Pages.LoginApproveDevicePage"
+    xmlns:pages="clr-namespace:Bit.App.Pages"
+    xmlns:u="clr-namespace:Bit.App.Utilities"
+    x:DataType="pages:LoginApproveDeviceViewModel"
+    x:Name="_page"
+    Title="{Binding PageTitle}">
+    
+    <ContentPage.BindingContext>
+        <pages:LoginApproveDeviceViewModel />
+    </ContentPage.BindingContext>
+
+    <StackLayout Padding="10, 10">
+        <StackLayout Padding="5, 10" Orientation="Horizontal">
+            <StackLayout HorizontalOptions="FillAndExpand">
+                <Label
+                    StyleClass="text-md"
+                    Text="{u:I18n RememberThisDevice}"/>
+                <Label
+                    StyleClass="box-sub-label"
+                    Text="{u:I18n TurnOffUsingPublicDevice}"/>
+            </StackLayout>
+            <Switch
+                Scale="0.8"
+                IsToggled="{Binding RememberThisDevice}"
+                VerticalOptions="Center"/>
+        </StackLayout>
+        <StackLayout Margin="0, 20, 0, 0">
+            <Button
+                x:Name="_continue"
+                Text="{u:I18n Continue}" 
+                StyleClass="btn-primary"
+                Command="{Binding ContinueCommand}"
+                IsVisible="{Binding ContinueEnabled}"/>
+            <Button
+                x:Name="_approveWithMyOtherDevice"
+                Text="{u:I18n ApproveWithMyOtherDevice}" 
+                StyleClass="btn-primary"
+                Command="{Binding ApproveWithMyOtherDeviceCommand}"
+                IsVisible="{Binding ApproveWithMyOtherDeviceEnabled}"/>
+            <Button
+                x:Name="_requestAdminApproval"
+                Text="{u:I18n RequestAdminApproval}" 
+                StyleClass="box-button-row"
+                Command="{Binding RequestAdminApprovalCommand}"
+                IsVisible="{Binding RequestAdminApprovalEnabled}"/>
+            <Button
+                x:Name="_approveWithMasterPassword"
+                Text="{u:I18n ApproveWithMasterPassword}" 
+                StyleClass="box-button-row"
+                Command="{Binding ApproveWithMasterPasswordCommand}"
+                IsVisible="{Binding ApproveWithMasterPasswordEnabled}"/>
+            <Label
+                Text="{Binding LoggingInAsText}"
+                StyleClass="text-sm"
+                Margin="0,40,0,0"
+                AutomationId="LoggingInAsLabel"
+                />
+            <Label
+                Text="{u:I18n NotYou}"
+                StyleClass="text-md"
+                HorizontalOptions="Start"
+                TextColor="{DynamicResource HyperlinkColor}"
+                AutomationId="NotYouLabel">
+                <Label.GestureRecognizers>
+                    <TapGestureRecognizer Tapped="Cancel_Clicked" />
+                </Label.GestureRecognizers>
+            </Label>
+        </StackLayout>
+    </StackLayout>
+</pages:BaseContentPage>
+
+

src/App/Pages/Accounts/LoginApproveDevicePage.xaml.cs

@@ -0,0 +1,62 @@
+using System;
+using System.Collections.Generic;
+using System.Threading.Tasks;
+using Bit.App.Models;
+using Bit.App.Utilities;
+using Bit.Core.Enums;
+using Bit.Core.Utilities;
+using Xamarin.Forms;
+
+namespace Bit.App.Pages
+{
+    public partial class LoginApproveDevicePage : BaseContentPage
+    {
+
+        private readonly LoginApproveDeviceViewModel _vm;
+        private readonly AppOptions _appOptions;
+
+        public LoginApproveDevicePage(AppOptions appOptions = null)
+        {
+            InitializeComponent();
+            _vm = BindingContext as LoginApproveDeviceViewModel;
+            _vm.LogInWithMasterPasswordAction = () => StartLogInWithMasterPassword().FireAndForget();
+            _vm.LogInWithDeviceAction = () => StartLoginWithDeviceAsync().FireAndForget();
+            _vm.RequestAdminApprovalAction = () => RequestAdminApprovalAsync().FireAndForget();
+            _vm.CloseAction = () => { Navigation.PopModalAsync(); };
+            _vm.Page = this;
+            _appOptions = appOptions;
+        }
+
+        protected override void OnAppearing()
+        {
+            _vm.InitAsync();
+        }
+
+        private void Cancel_Clicked(object sender, EventArgs e)
+        {
+            if (DoOnce())
+            {
+                _vm.CloseAction();
+            }
+        }
+
+        private async Task StartLogInWithMasterPassword()
+        {
+            var page = new LockPage(_appOptions);
+            await Navigation.PushModalAsync(new NavigationPage(page));
+        }
+
+        private async Task StartLoginWithDeviceAsync()
+        {
+            var page = new LoginPasswordlessRequestPage(_vm.Email, AuthRequestType.AuthenticateAndUnlock, _appOptions);
+            await Navigation.PushModalAsync(new NavigationPage(page));
+        }
+
+        private async Task RequestAdminApprovalAsync()
+        {
+            var page = new LoginPasswordlessRequestPage(_vm.Email, AuthRequestType.AdminApproval, _appOptions);
+            await Navigation.PushModalAsync(new NavigationPage(page));
+        }
+    }
+}
+

src/App/Pages/Accounts/LoginApproveDeviceViewModel.cs

@@ -0,0 +1,132 @@
+using System;
+using System.Threading.Tasks;
+using System.Windows.Input;
+using Bit.App.Abstractions;
+using Bit.App.Resources;
+using Bit.App.Utilities.AccountManagement;
+using Bit.Core.Abstractions;
+using Bit.Core.Enums;
+using Bit.Core.Models.Request;
+using Bit.Core.Services;
+using Bit.Core.Utilities;
+using Xamarin.CommunityToolkit.ObjectModel;
+using Xamarin.Essentials;
+using Xamarin.Forms;
+
+namespace Bit.App.Pages
+{
+    public class LoginApproveDeviceViewModel : BaseViewModel
+    {
+        private bool _rememberThisDevice;
+        private bool _approveWithMyOtherDeviceEnabled;
+        private bool _requestAdminApprovalEnabled;
+        private bool _approveWithMasterPasswordEnabled;
+        private bool _continueEnabled;
+        private string _email;
+        private readonly IStateService _stateService;
+        private readonly IApiService _apiService;
+        private IDeviceTrustCryptoService _deviceTrustCryptoService;
+
+        public ICommand ApproveWithMyOtherDeviceCommand { get; }
+        public ICommand RequestAdminApprovalCommand { get; }
+        public ICommand ApproveWithMasterPasswordCommand { get; }
+        public ICommand ContinueCommand { get; }
+
+        public Action LogInWithMasterPasswordAction { get; set; }
+        public Action LogInWithDeviceAction { get; set; }
+        public Action RequestAdminApprovalAction { get; set; }
+        public Action CloseAction { get; set; }
+
+        public LoginApproveDeviceViewModel()
+        {
+            _stateService = ServiceContainer.Resolve<IStateService>();
+            _apiService = ServiceContainer.Resolve<IApiService>();
+            _deviceTrustCryptoService = ServiceContainer.Resolve<IDeviceTrustCryptoService>();
+
+            PageTitle = AppResources.LoggedIn;
+
+            ApproveWithMyOtherDeviceCommand = new AsyncCommand(() => SetDeviceTrustAndInvokeAsync(LogInWithDeviceAction),
+                onException: ex => HandleException(ex),
+                allowsMultipleExecutions: false);
+
+            RequestAdminApprovalCommand = new AsyncCommand(() => SetDeviceTrustAndInvokeAsync(RequestAdminApprovalAction),
+                onException: ex => HandleException(ex),
+                allowsMultipleExecutions: false);
+
+            ApproveWithMasterPasswordCommand = new AsyncCommand(() => SetDeviceTrustAndInvokeAsync(LogInWithMasterPasswordAction),
+                onException: ex => HandleException(ex),
+                allowsMultipleExecutions: false);
+
+            ContinueCommand = new AsyncCommand(InitAsync,
+                onException: ex => HandleException(ex),
+                allowsMultipleExecutions: false);
+        }
+
+        public string LoggingInAsText => string.Format(AppResources.LoggingInAsX, Email);
+
+        public bool RememberThisDevice
+        {
+            get => _rememberThisDevice;
+            set => SetProperty(ref _rememberThisDevice, value);
+        }
+
+        public bool ApproveWithMyOtherDeviceEnabled
+        {
+            get => _approveWithMyOtherDeviceEnabled;
+            set => SetProperty(ref _approveWithMyOtherDeviceEnabled, value);
+        }
+
+        public bool RequestAdminApprovalEnabled
+        {
+            get => _requestAdminApprovalEnabled;
+            set => SetProperty(ref _requestAdminApprovalEnabled, value);
+        }
+
+        public bool ApproveWithMasterPasswordEnabled
+        {
+            get => _approveWithMasterPasswordEnabled;
+            set => SetProperty(ref _approveWithMasterPasswordEnabled, value);
+        }
+
+        public bool ContinueEnabled
+        {
+            get => _continueEnabled;
+            set => SetProperty(ref _continueEnabled, value);
+        }
+
+        public string Email
+        {
+            get => _email;
+            set => SetProperty(ref _email, value, additionalPropertyNames:
+                new string[] {
+                    nameof(LoggingInAsText)
+                });
+        }
+
+        public async Task InitAsync()
+        {
+            try
+            {
+                Email = await _stateService.GetRememberedEmailAsync();
+                var decryptOptions = await _stateService.GetAccountDecryptionOptions();
+                RequestAdminApprovalEnabled = decryptOptions?.TrustedDeviceOption?.HasAdminApproval ?? false;
+                ApproveWithMasterPasswordEnabled = decryptOptions?.HasMasterPassword ?? false;
+                ApproveWithMyOtherDeviceEnabled = decryptOptions?.TrustedDeviceOption?.HasLoginApprovingDevice ?? false;
+            }
+            catch (Exception ex)
+            {
+                HandleException(ex);
+            }
+
+            // TODO: Change this expression to, Appear if the browser is trusted and shared the key with the app
+            ContinueEnabled = !RequestAdminApprovalEnabled && !ApproveWithMasterPasswordEnabled && !ApproveWithMyOtherDeviceEnabled;
+        }
+
+        private async Task SetDeviceTrustAndInvokeAsync(Action action)
+        {
+            await _deviceTrustCryptoService.SetShouldTrustDeviceAsync(RememberThisDevice);
+            await Device.InvokeOnMainThreadAsync(action);
+        }
+    }
+}
+

src/App/Pages/Accounts/LoginPage.xaml.cs

@@ -4,6 +4,7 @@ using Bit.App.Models;
 using Bit.App.Utilities;
 using Bit.Core;
 using Bit.Core.Abstractions;
+using Bit.Core.Enums;
 using Bit.Core.Services;
 using Bit.Core.Utilities;
 using Xamarin.CommunityToolkit.ObjectModel;
@@ -135,7 +136,7 @@ namespace Bit.App.Pages
 
         private async Task StartLoginWithDeviceAsync()
         {
-            var page = new LoginPasswordlessRequestPage(_vm.Email, _appOptions);
+            var page = new LoginPasswordlessRequestPage(_vm.Email, AuthRequestType.AuthenticateAndUnlock, _appOptions);
             await Navigation.PushModalAsync(new NavigationPage(page));
         }
 

src/App/Pages/Accounts/LoginPasswordlessRequestPage.xaml

@@ -21,17 +21,17 @@
         <StackLayout
             Padding="7, 0, 7, 20">
             <Label
-                Text="{u:I18n LogInInitiated}"
+                Text="{Binding Tittle}"
                 FontSize="Title"
                 FontAttributes="Bold"
                 Margin="0,14,0,21"
                 AutomationId="LogInInitiatedLabel" />
             <Label
-                Text="{u:I18n ANotificationHasBeenSentToYourDevice}"
+                Text="{Binding SubTittle}"
                 FontSize="Small"
                 Margin="0,0,0,10"/>
             <Label
-                Text="{u:I18n PleaseMakeSureYourVaultIsUnlockedAndTheFingerprintPhraseMatchesOnTheOtherDevice}"
+                Text="{Binding Description}"
                 FontSize="Small"
                 Margin="0,0,0,24"/>
             <Label
@@ -45,6 +45,7 @@
                 AutomationId="FingerprintPhraseValue" />
             <Label
                 Text="{u:I18n ResendNotification}"
+                IsVisible="{Binding ResendNotificationVisible}"
                 StyleClass="text-md"
                 HorizontalOptions="Start"
                 Margin="0,40,0,0"
@@ -58,7 +59,7 @@
                 Orientation="Horizontal"
                 Margin="0,30,0,0">
                 <Label
-                    Text="{u:I18n NeedAnotherOption}"
+                    Text="{Binding OtherOptions}"
                     FontSize="Small"
                     VerticalTextAlignment="End"/>
                 <Label

src/App/Pages/Accounts/LoginPasswordlessRequestPage.xaml.cs

@@ -3,6 +3,7 @@ using System.Collections.Generic;
 using System.Threading.Tasks;
 using Bit.App.Models;
 using Bit.App.Utilities;
+using Bit.Core.Enums;
 using Xamarin.Forms;
 
 namespace Bit.App.Pages
@@ -12,13 +13,14 @@ namespace Bit.App.Pages
         private LoginPasswordlessRequestViewModel _vm;
         private readonly AppOptions _appOptions;
 
-        public LoginPasswordlessRequestPage(string email, AppOptions appOptions = null)
+        public LoginPasswordlessRequestPage(string email, AuthRequestType authRequestType, AppOptions appOptions = null)
         {
             InitializeComponent();
             _appOptions = appOptions;
             _vm = BindingContext as LoginPasswordlessRequestViewModel;
             _vm.Page = this;
             _vm.Email = email;
+            _vm.AuthRequestType = authRequestType;
             _vm.StartTwoFactorAction = () => Device.BeginInvokeOnMainThread(async () => await StartTwoFactorAsync());
             _vm.LogInSuccessAction = () => Device.BeginInvokeOnMainThread(async () => await LogInSuccessAsync());
             _vm.UpdateTempPasswordAction = () => Device.BeginInvokeOnMainThread(async () => await UpdateTempPasswordAsync());

src/App/Pages/Accounts/LoginPasswordlessRequestViewModel.cs

@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.Linq;
+using System.Net.Http;
 using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
@@ -12,6 +13,7 @@ using Bit.Core;
 using Bit.Core.Abstractions;
 using Bit.Core.Enums;
 using Bit.Core.Models.Domain;
+using Bit.Core.Models.Response;
 using Bit.Core.Services;
 using Bit.Core.Utilities;
 using Xamarin.CommunityToolkit.ObjectModel;
@@ -32,6 +34,9 @@ namespace Bit.App.Pages
         private IPlatformUtilsService _platformUtilsService;
         private IEnvironmentService _environmentService;
         private ILogger _logger;
+        private IDeviceTrustCryptoService _deviceTrustCryptoService;
+        private readonly ICryptoFunctionService _cryptoFunctionService;
+        private readonly ICryptoService _cryptoService;
 
         protected override II18nService i18nService => _i18nService;
         protected override IEnvironmentService environmentService => _environmentService;
@@ -44,6 +49,7 @@ namespace Bit.App.Pages
         private string _email;
         private string _requestId;
         private string _requestAccessCode;
+        private AuthRequestType _authRequestType;
         // Item1 publicKey, Item2 privateKey
         private Tuple<byte[], byte[]> _requestKeyPair;
 
@@ -57,6 +63,9 @@ namespace Bit.App.Pages
             _i18nService = ServiceContainer.Resolve<II18nService>();
             _stateService = ServiceContainer.Resolve<IStateService>();
             _logger = ServiceContainer.Resolve<ILogger>();
+            _deviceTrustCryptoService = ServiceContainer.Resolve<IDeviceTrustCryptoService>();
+            _cryptoFunctionService = ServiceContainer.Resolve<ICryptoFunctionService>();
+            _cryptoService = ServiceContainer.Resolve<ICryptoService>();
 
             PageTitle = AppResources.LogInWithAnotherDevice;
 
@@ -77,6 +86,70 @@ namespace Bit.App.Pages
         public ICommand CreatePasswordlessLoginCommand { get; }
         public ICommand CloseCommand { get; }
 
+        public string Tittle
+        {
+            get
+            {
+                switch (_authRequestType)
+                {
+                    case AuthRequestType.AuthenticateAndUnlock:
+                        return AppResources.LogInInitiated;
+                    case AuthRequestType.AdminApproval:
+                        return AppResources.AdminApprovalRequested;
+                    default:
+                        return string.Empty;
+                };
+            }
+        }
+
+        public string SubTittle
+        {
+            get
+            {
+                switch (_authRequestType)
+                {
+                    case AuthRequestType.AuthenticateAndUnlock:
+                        return AppResources.ANotificationHasBeenSentToYourDevice;
+                    case AuthRequestType.AdminApproval:
+                        return AppResources.YourRequestHasBeenSentToYourAdmin;
+                    default:
+                        return string.Empty;
+                };
+            }
+        }
+
+        public string Description
+        {
+            get
+            {
+                switch (_authRequestType)
+                {
+                    case AuthRequestType.AuthenticateAndUnlock:
+                        return AppResources.PleaseMakeSureYourVaultIsUnlockedAndTheFingerprintPhraseMatchesOnTheOtherDevice;
+                    case AuthRequestType.AdminApproval:
+                        return AppResources.YouWillBeNotifiedOnceApproved;
+                    default:
+                        return string.Empty;
+                };
+            }
+        }
+
+        public string OtherOptions
+        {
+            get
+            {
+                switch (_authRequestType)
+                {
+                    case AuthRequestType.AuthenticateAndUnlock:
+                        return AppResources.NeedAnotherOption;
+                    case AuthRequestType.AdminApproval:
+                        return AppResources.TroubleLoggingIn;
+                    default:
+                        return string.Empty;
+                };
+            }
+        }
+
         public string FingerprintPhrase
         {
             get => _fingerprintPhrase;
@@ -89,6 +162,21 @@ namespace Bit.App.Pages
             set => SetProperty(ref _email, value);
         }
 
+        public AuthRequestType AuthRequestType
+        {
+            get => _authRequestType;
+            set => SetProperty(ref _authRequestType, value, additionalPropertyNames: new string[]
+            {
+                nameof(Tittle),
+                nameof(SubTittle),
+                nameof(Description),
+                nameof(OtherOptions),
+                nameof(ResendNotificationVisible)
+            });
+        }
+
+        public bool ResendNotificationVisible => AuthRequestType == AuthRequestType.AuthenticateAndUnlock;
+
         public void StartCheckLoginRequestStatus()
         {
             try
@@ -119,14 +207,22 @@ namespace Bit.App.Pages
 
         private async Task CheckLoginRequestStatus()
         {
-            if (string.IsNullOrEmpty(_requestId) || string.IsNullOrEmpty(_requestAccessCode))
+            if (string.IsNullOrEmpty(_requestId))
             {
                 return;
             }
 
             try
             {
-                var response = await _authService.GetPasswordlessLoginResponseAsync(_requestId, _requestAccessCode);
+                PasswordlessLoginResponse response = null;
+                if (await _stateService.IsAuthenticatedAsync())
+                {
+                    response = await _authService.GetPasswordlessLoginRequestByIdAsync(_requestId);
+                }
+                else
+                {
+                    response = await _authService.GetPasswordlessLoginResquestAsync(_requestId, _requestAccessCode);
+                }
 
                 if (response.RequestApproved == null || !response.RequestApproved.Value)
                 {
@@ -138,6 +234,12 @@ namespace Bit.App.Pages
                 var authResult = await _authService.LogInPasswordlessAsync(Email, _requestAccessCode, _requestId, _requestKeyPair.Item2, response.Key, response.MasterPasswordHash);
                 await AppHelpers.ResetInvalidUnlockAttemptsAsync();
 
+                if (authResult == null && await _stateService.IsAuthenticatedAsync())
+                {
+                    await HandleLoginCompleteAsync();
+                    return;
+                }
+
                 if (await HandleCaptchaAsync(authResult.CaptchaSiteKey, authResult.CaptchaNeeded, CheckLoginRequestStatus))
                 {
                     return;
@@ -153,8 +255,7 @@ namespace Bit.App.Pages
                 }
                 else
                 {
-                    _syncService.FullSyncAsync(true).FireAndForget();
+                    await HandleLoginCompleteAsync();
-                    LogInSuccessAction?.Invoke();
                 }
             }
             catch (Exception ex)
@@ -164,22 +265,66 @@ namespace Bit.App.Pages
             }
         }
 
+        private async Task HandleLoginCompleteAsync()
+        {
+            await _stateService.SetPendingAdminAuthRequestAsync(null);
+            _syncService.FullSyncAsync(true).FireAndForget();
+            LogInSuccessAction?.Invoke();
+        }
+
         private async Task CreatePasswordlessLoginAsync()
         {
             await Device.InvokeOnMainThreadAsync(() => _deviceActionService.ShowLoadingAsync(AppResources.Loading));
 
-            var response = await _authService.PasswordlessCreateLoginRequestAsync(_email);
+            PasswordlessLoginResponse response = null;
-            if (response != null)
+            var pendingRequest = await _stateService.GetPendingAdminAuthRequestAsync();
+            if (pendingRequest != null && _authRequestType == AuthRequestType.AdminApproval)
             {
+                response = await _authService.GetPasswordlessLoginRequestByIdAsync(pendingRequest.Id);
+                if (response == null || (response.IsAnswered && !response.RequestApproved.Value))
+                {
+                    // handle pending auth request not valid remove it from state
+                    await _stateService.SetPendingAdminAuthRequestAsync(null);
+                    pendingRequest = null;
+                }
+                else
+                {
+                    // Derive pubKey from privKey in state to avoid MITM attacks
+                    // Also generate FingerprintPhrase locally for the same reason
+                    var derivedPublicKey = await _cryptoFunctionService.RsaExtractPublicKeyAsync(pendingRequest.PrivateKey);
+                    response.FingerprintPhrase = string.Join("-", await _cryptoService.GetFingerprintAsync(Email, derivedPublicKey));
+                    response.RequestKeyPair = new Tuple<byte[], byte[]>(derivedPublicKey, pendingRequest.PrivateKey);
+                }
+            }
+
+            if (response == null)
+            {
+                response = await _authService.PasswordlessCreateLoginRequestAsync(_email, AuthRequestType);
+            }
+
+            await HandlePasswordlessLoginAsync(response, pendingRequest == null && _authRequestType == AuthRequestType.AdminApproval);
+            await _deviceActionService.HideLoadingAsync();
+        }
+
+        private async Task HandlePasswordlessLoginAsync(PasswordlessLoginResponse response, bool createPendingAdminRequest)
+        {
+            if (response == null)
+            {
+                throw new ArgumentNullException(nameof(response));
+            }
+
+            if (createPendingAdminRequest)
+            {
+                var pendingAuthRequest = new PendingAdminAuthRequest { Id = response.Id, PrivateKey = response.RequestKeyPair.Item2 };
+                await _stateService.SetPendingAdminAuthRequestAsync(pendingAuthRequest);
+            }
+
             FingerprintPhrase = response.FingerprintPhrase;
             _requestId = response.Id;
             _requestAccessCode = response.RequestAccessCode;
             _requestKeyPair = response.RequestKeyPair;
         }
 
-            await _deviceActionService.HideLoadingAsync();
-        }
-
         private void HandleException(Exception ex)
         {
             Xamarin.Essentials.MainThread.InvokeOnMainThreadAsync(async () =>

src/App/Pages/Accounts/LoginSsoPage.xaml.cs

@@ -29,6 +29,8 @@ namespace Bit.App.Pages
             _vm.SsoAuthSuccessAction = () => Device.BeginInvokeOnMainThread(async () => await SsoAuthSuccessAsync());
             _vm.UpdateTempPasswordAction =
                 () => Device.BeginInvokeOnMainThread(async () => await UpdateTempPasswordAsync());
+            _vm.StartDeviceApprovalOptionsAction =
+                () => Device.BeginInvokeOnMainThread(async () => await StartDeviceApprovalOptionsAsync());
             _vm.CloseAction = async () =>
             {
                 await Navigation.PopModalAsync();
@@ -106,10 +108,17 @@ namespace Bit.App.Pages
             await Navigation.PushModalAsync(new NavigationPage(page));
         }
 
+        private async Task StartDeviceApprovalOptionsAsync()
+        {
+            var page = new LoginApproveDevicePage();
+            await Navigation.PushModalAsync(new NavigationPage(page));
+        }
+
         private async Task SsoAuthSuccessAsync()
         {
             RestoreAppOptionsFromCopy();
             await AppHelpers.ClearPreviousPage();
+
             if (await _vaultTimeoutService.IsLockedAsync())
             {
                 Application.Current.MainPage = new NavigationPage(new LockPage(_appOptions));

src/App/Pages/Accounts/LoginSsoPageViewModel.cs

@@ -9,6 +9,7 @@ using Bit.Core.Abstractions;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Models.Domain;
+using Bit.Core.Services;
 using Bit.Core.Utilities;
 using Xamarin.CommunityToolkit.ObjectModel;
 using Xamarin.Essentials;
@@ -29,6 +30,8 @@ namespace Bit.App.Pages
         private readonly IStateService _stateService;
         private readonly ILogger _logger;
         private readonly IOrganizationService _organizationService;
+        private readonly IDeviceTrustCryptoService _deviceTrustCryptoService;
+        private readonly ICryptoService _cryptoService;
 
         private string _orgIdentifier;
 
@@ -45,7 +48,8 @@ namespace Bit.App.Pages
             _stateService = ServiceContainer.Resolve<IStateService>("stateService");
             _logger = ServiceContainer.Resolve<ILogger>("logger");
             _organizationService = ServiceContainer.Resolve<IOrganizationService>();
-
+            _deviceTrustCryptoService = ServiceContainer.Resolve<IDeviceTrustCryptoService>();
+            _cryptoService = ServiceContainer.Resolve<ICryptoService>();
 
             PageTitle = AppResources.Bitwarden;
             LogInCommand = new AsyncCommand(LogInAsync, allowsMultipleExecutions: false);
@@ -61,6 +65,7 @@ namespace Bit.App.Pages
         public Action StartTwoFactorAction { get; set; }
         public Action StartSetPasswordAction { get; set; }
         public Action SsoAuthSuccessAction { get; set; }
+        public Action StartDeviceApprovalOptionsAction { get; set; }
         public Action CloseAction { get; set; }
         public Action UpdateTempPasswordAction { get; set; }
 
@@ -197,6 +202,7 @@ namespace Bit.App.Pages
             try
             {
                 var response = await _authService.LogInSsoAsync(code, codeVerifier, REDIRECT_URI, orgId);
+                var decryptOptions = await _stateService.GetAccountDecryptionOptions();
                 await AppHelpers.ResetInvalidUnlockAttemptsAsync();
                 await _stateService.SetRememberedOrgIdentifierAsync(OrgIdentifier);
                 await _deviceActionService.HideLoadingAsync();
@@ -212,9 +218,31 @@ namespace Bit.App.Pages
                 {
                     UpdateTempPasswordAction?.Invoke();
                 }
+                else if (decryptOptions?.TrustedDeviceOption != null)
+                {
+                    // If user doesn't have a MP, but has reset password permission, they must set a MP
+                    if (!decryptOptions.HasMasterPassword &&
+                        decryptOptions.TrustedDeviceOption.HasManageResetPasswordPermission)
+                    {
+                        StartSetPasswordAction?.Invoke();
+                    }
+                    else if (response.ForcePasswordReset)
+                    {
+                        UpdateTempPasswordAction?.Invoke();
+                    }
+                    else if (await _deviceTrustCryptoService.IsDeviceTrustedAsync())
+                    {
+                        _syncService.FullSyncAsync(true).FireAndForget();
+                        SsoAuthSuccessAction?.Invoke();
+                    }
                     else
                     {
-                    var task = Task.Run(async () => await _syncService.FullSyncAsync(true));
+                        StartDeviceApprovalOptionsAction?.Invoke();
+                    }
+                }
+                else
+                {
+                    _syncService.FullSyncAsync(true).FireAndForget();
                     SsoAuthSuccessAction?.Invoke();
                 }
             }

src/App/Pages/Accounts/RegisterPageViewModel.cs

@@ -177,25 +177,28 @@ namespace Bit.App.Pages
             Name = string.IsNullOrWhiteSpace(Name) ? null : Name;
             Email = Email.Trim().ToLower();
             var kdfConfig = new KdfConfig(KdfType.PBKDF2_SHA256, Constants.Pbkdf2Iterations, null, null);
-            var key = await _cryptoService.MakeKeyAsync(MasterPassword, Email, kdfConfig);
+            var newMasterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, Email, kdfConfig);
-            var encKey = await _cryptoService.MakeEncKeyAsync(key);
+            var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(
-            var hashedPassword = await _cryptoService.HashPasswordAsync(MasterPassword, key);
+                newMasterKey,
-            var keys = await _cryptoService.MakeKeyPairAsync(encKey.Item1);
+                await _cryptoService.MakeUserKeyAsync()
+            );
+            var hashedPassword = await _cryptoService.HashPasswordAsync(MasterPassword, newMasterKey);
+            var (newPublicKey, newProtectedPrivateKey) = await _cryptoService.MakeKeyPairAsync(newUserKey);
             var request = new RegisterRequest
             {
                 Email = Email,
                 Name = Name,
                 MasterPasswordHash = hashedPassword,
                 MasterPasswordHint = Hint,
-                Key = encKey.Item2.EncryptedString,
+                Key = newProtectedUserKey.EncryptedString,
                 Kdf = kdfConfig.Type,
                 KdfIterations = kdfConfig.Iterations,
                 KdfMemory = kdfConfig.Memory,
                 KdfParallelism = kdfConfig.Parallelism,
                 Keys = new KeysRequest
                 {
-                    PublicKey = keys.Item1,
+                    PublicKey = newPublicKey,
-                    EncryptedPrivateKey = keys.Item2.EncryptedString
+                    EncryptedPrivateKey = newProtectedPrivateKey.EncryptedString
                 },
                 CaptchaResponse = _captchaToken,
             };

src/App/Pages/Accounts/SetPasswordPageViewModel.cs

@@ -165,26 +165,18 @@ namespace Bit.App.Pages
 
             var kdfConfig = new KdfConfig(KdfType.PBKDF2_SHA256, Constants.Pbkdf2Iterations, null, null);
             var email = await _stateService.GetEmailAsync();
-            var key = await _cryptoService.MakeKeyAsync(MasterPassword, email, kdfConfig);
+            var newMasterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, email, kdfConfig);
-            var masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.ServerAuthorization);
+            var masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, newMasterKey, HashPurpose.ServerAuthorization);
-            var localMasterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.LocalAuthorization);
+            var localMasterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, newMasterKey, HashPurpose.LocalAuthorization);
 
-            Tuple<SymmetricCryptoKey, EncString> encKey;
+            var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(newMasterKey,
-            var existingEncKey = await _cryptoService.GetEncKeyAsync();
+                await _cryptoService.GetUserKeyAsync() ?? await _cryptoService.MakeUserKeyAsync());
-            if (existingEncKey == null)
-            {
-                encKey = await _cryptoService.MakeEncKeyAsync(key);
-            }
-            else
-            {
-                encKey = await _cryptoService.RemakeEncKeyAsync(key);
-            }
 
-            var keys = await _cryptoService.MakeKeyPairAsync(encKey.Item1);
+            var keys = await _cryptoService.MakeKeyPairAsync(newUserKey);
             var request = new SetPasswordRequest
             {
                 MasterPasswordHash = masterPasswordHash,
-                Key = encKey.Item2.EncryptedString,
+                Key = newProtectedUserKey.EncryptedString,
                 MasterPasswordHint = Hint,
                 Kdf = kdfConfig.Type.GetValueOrDefault(KdfType.PBKDF2_SHA256),
                 KdfIterations = kdfConfig.Iterations.GetValueOrDefault(Constants.Pbkdf2Iterations),
@@ -204,19 +196,19 @@ namespace Bit.App.Pages
                 // Set Password and relevant information
                 await _apiService.SetPasswordAsync(request);
                 await _stateService.SetKdfConfigurationAsync(kdfConfig);
-                await _cryptoService.SetKeyAsync(key);
+                await _cryptoService.SetMasterKeyAsync(newMasterKey);
-                await _cryptoService.SetKeyHashAsync(localMasterPasswordHash);
+                await _cryptoService.SetPasswordHashAsync(localMasterPasswordHash);
-                await _cryptoService.SetEncKeyAsync(encKey.Item2.EncryptedString);
+                await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(newProtectedUserKey.EncryptedString);
-                await _cryptoService.SetEncPrivateKeyAsync(keys.Item2.EncryptedString);
+                await _cryptoService.SetPrivateKeyAsync(keys.Item2.EncryptedString);
 
                 if (ResetPasswordAutoEnroll)
                 {
                     // Grab Organization Keys
                     var response = await _apiService.GetOrganizationKeysAsync(OrgId);
                     var publicKey = CoreHelpers.Base64UrlDecode(response.PublicKey);
-                    // Grab user's Encryption Key and encrypt with Org Public Key
+                    // Grab User Key and encrypt with Org Public Key
-                    var userEncKey = await _cryptoService.GetEncKeyAsync();
+                    var userKey = await _cryptoService.GetUserKeyAsync();
-                    var encryptedKey = await _cryptoService.RsaEncryptAsync(userEncKey.Key, publicKey);
+                    var encryptedKey = await _cryptoService.RsaEncryptAsync(userKey.Key, publicKey);
                     // Request
                     var resetRequest = new OrganizationUserResetPasswordEnrollmentRequest
                     {

src/App/Pages/Accounts/TwoFactorPage.xaml.cs

@@ -37,6 +37,8 @@ namespace Bit.App.Pages
                 Device.BeginInvokeOnMainThread(async () => await TwoFactorAuthSuccessAsync());
             _vm.UpdateTempPasswordAction =
                 () => Device.BeginInvokeOnMainThread(async () => await UpdateTempPasswordAsync());
+            _vm.StartDeviceApprovalOptionsAction =
+                () => Device.BeginInvokeOnMainThread(async () => await StartDeviceApprovalOptionsAsync());
             _vm.CloseAction = async () => await Navigation.PopModalAsync();
             DuoWebView = _duoWebView;
             if (Device.RuntimePlatform == Device.Android)
@@ -180,6 +182,12 @@ namespace Bit.App.Pages
             await Navigation.PushModalAsync(new NavigationPage(page));
         }
 
+        private async Task StartDeviceApprovalOptionsAsync()
+        {
+            var page = new LoginApproveDevicePage();
+            await Navigation.PushModalAsync(new NavigationPage(page));
+        }
+
         private async Task TwoFactorAuthSuccessAsync()
         {
             if (_authingWithSso)

src/App/Pages/Accounts/TwoFactorPageViewModel.cs

@@ -11,6 +11,7 @@ using Bit.Core.Abstractions;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Models.Request;
+using Bit.Core.Services;
 using Bit.Core.Utilities;
 using Newtonsoft.Json;
 using Xamarin.CommunityToolkit.ObjectModel;
@@ -33,7 +34,7 @@ namespace Bit.App.Pages
         private readonly II18nService _i18nService;
         private readonly IAppIdService _appIdService;
         private readonly ILogger _logger;
-
+        private readonly IDeviceTrustCryptoService _deviceTrustCryptoService;
         private TwoFactorProviderType? _selectedProviderType;
         private string _totpInstruction;
         private string _webVaultUrl = "https://vault.bitwarden.com";
@@ -55,6 +56,7 @@ namespace Bit.App.Pages
             _i18nService = ServiceContainer.Resolve<II18nService>("i18nService");
             _appIdService = ServiceContainer.Resolve<IAppIdService>("appIdService");
             _logger = ServiceContainer.Resolve<ILogger>();
+            _deviceTrustCryptoService = ServiceContainer.Resolve<IDeviceTrustCryptoService>();
 
             PageTitle = AppResources.TwoStepLogin;
             SubmitCommand = new Command(async () => await SubmitAsync());
@@ -118,6 +120,7 @@ namespace Bit.App.Pages
         public Command SubmitCommand { get; }
         public ICommand MoreCommand { get; }
         public Action TwoFactorAuthSuccessAction { get; set; }
+        public Action StartDeviceApprovalOptionsAction { get; set; }
         public Action StartSetPasswordAction { get; set; }
         public Action CloseAction { get; set; }
         public Action UpdateTempPasswordAction { get; set; }
@@ -315,6 +318,7 @@ namespace Bit.App.Pages
 
                 var task = Task.Run(() => _syncService.FullSyncAsync(true));
                 await _deviceActionService.HideLoadingAsync();
+                var decryptOptions = await _stateService.GetAccountDecryptionOptions();
                 _messagingService.Send("listenYubiKeyOTP", false);
                 _broadcasterService.Unsubscribe(nameof(TwoFactorPage));
 
@@ -326,6 +330,27 @@ namespace Bit.App.Pages
                 {
                     UpdateTempPasswordAction?.Invoke();
                 }
+                else if (decryptOptions?.TrustedDeviceOption != null)
+                {
+                    // If user doesn't have a MP, but has reset password permission, they must set a MP
+                    if (!decryptOptions.HasMasterPassword &&
+                        decryptOptions.TrustedDeviceOption.HasManageResetPasswordPermission)
+                    {
+                        StartSetPasswordAction?.Invoke();
+                    }
+                    else if (result.ForcePasswordReset)
+                    {
+                        UpdateTempPasswordAction?.Invoke();
+                    }
+                    else if (await _deviceTrustCryptoService.IsDeviceTrustedAsync())
+                    {
+                        TwoFactorAuthSuccessAction?.Invoke();
+                    }
+                    else
+                    {
+                        StartDeviceApprovalOptionsAction?.Invoke();
+                    }
+                }
                 else
                 {
                     TwoFactorAuthSuccessAction?.Invoke();

src/App/Pages/Accounts/UpdateTempPasswordPageViewModel.cs

@@ -93,12 +93,12 @@ namespace Bit.App.Pages
             var kdfConfig = await _stateService.GetActiveUserCustomDataAsync(a => new KdfConfig(a?.Profile));
             var email = await _stateService.GetEmailAsync();
 
-            // Create new key and hash new password
+            // Create new master key and hash new password
-            var key = await _cryptoService.MakeKeyAsync(MasterPassword, email, kdfConfig);
+            var masterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, email, kdfConfig);
-            var masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key);
+            var masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, masterKey);
 
-            // Create new encKey for the User
+            // Encrypt user key with new master key
-            var newEncKey = await _cryptoService.RemakeEncKeyAsync(key);
+            var (userKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(masterKey);
 
             // Initiate API action
             try
@@ -108,10 +108,10 @@ namespace Bit.App.Pages
                 switch (_reason)
                 {
                     case ForcePasswordResetReason.AdminForcePasswordReset:
-                        await UpdateTempPasswordAsync(masterPasswordHash, newEncKey.Item2.EncryptedString);
+                        await UpdateTempPasswordAsync(masterPasswordHash, newProtectedUserKey.EncryptedString);
                         break;
                     case ForcePasswordResetReason.WeakMasterPasswordOnLogin:
-                        await UpdatePasswordAsync(masterPasswordHash, newEncKey.Item2.EncryptedString);
+                        await UpdatePasswordAsync(masterPasswordHash, newProtectedUserKey.EncryptedString);
                         break;
                     default:
                         throw new ArgumentOutOfRangeException();

src/App/Pages/Settings/SettingsPage/SettingsPageViewModel.cs

@@ -48,6 +48,7 @@ namespace Bit.App.Pages
         private bool _reportLoggingEnabled;
         private bool _approvePasswordlessLoginRequests;
         private bool _shouldConnectToWatch;
+        private bool _hasMasterPassword;
         private readonly static List<KeyValuePair<string, int?>> VaultTimeoutOptions =
             new List<KeyValuePair<string, int?>>
             {
@@ -100,12 +101,17 @@ namespace Bit.App.Pages
             ExecuteSettingItemCommand = new AsyncCommand<SettingsPageListItem>(item => item.ExecuteAsync(), onException: _loggerService.Exception, allowsMultipleExecutions: false);
         }
 
+        private bool IsVaultTimeoutActionLockAllowed => _hasMasterPassword || _biometric || _pin;
+
         public ObservableRangeCollection<ISettingsPageListItem> GroupedItems { get; set; }
 
         public IAsyncCommand<SettingsPageListItem> ExecuteSettingItemCommand { get; }
 
         public async Task InitAsync()
         {
+            var decryptionOptions = await _stateService.GetAccountDecryptionOptions();
+            // set has true for backwards compatibility
+            _hasMasterPassword = decryptionOptions?.HasMasterPassword ?? true;
             _supportsBiometric = await _platformUtilsService.SupportsBiometricAsync();
             var lastSync = await _syncService.GetLastSyncAsync();
             if (lastSync != null)
@@ -124,7 +130,13 @@ namespace Bit.App.Pages
             _vaultTimeoutDisplayValue = _vaultTimeoutOptions.FirstOrDefault(o => o.Value == _vaultTimeout).Key;
             _vaultTimeoutDisplayValue ??= _vaultTimeoutOptions.Where(o => o.Value == CustomVaultTimeoutValue).First().Key;
 
-            var action = await _vaultTimeoutService.GetVaultTimeoutAction() ?? VaultTimeoutAction.Lock;
+            var savedVaultTimeoutAction = await _vaultTimeoutService.GetVaultTimeoutAction();
+            var action = savedVaultTimeoutAction ?? VaultTimeoutAction.Lock;
+            if (!_hasMasterPassword && savedVaultTimeoutAction == null)
+            {
+                action = VaultTimeoutAction.Logout;
+                await _vaultTimeoutService.SetVaultTimeoutOptionsAsync(_vaultTimeout, VaultTimeoutAction.Logout);
+            }
             _vaultTimeoutActionDisplayValue = _vaultTimeoutActionOptions.FirstOrDefault(o => o.Value == action).Key;
 
             if (await _policyService.PolicyAppliesToUser(PolicyType.MaximumVaultTimeout))
@@ -139,7 +151,7 @@ namespace Bit.App.Pages
             }
 
             var pinSet = await _vaultTimeoutService.IsPinLockSetAsync();
-            _pin = pinSet.Item1 || pinSet.Item2;
+            _pin = pinSet != PinLockEnum.Disabled;
             _biometric = await _vaultTimeoutService.IsBiometricLockSetAsync();
             _screenCaptureAllowed = await _stateService.GetScreenCaptureAllowedAsync();
 
@@ -387,8 +399,11 @@ namespace Bit.App.Pages
                 // do nothing if we have a policy set
                 return;
             }
-            var options = _vaultTimeoutActionOptions.Select(o =>
+
-                o.Key == _vaultTimeoutActionDisplayValue ? $"✓ {o.Key}" : o.Key).ToArray();
+            var options = IsVaultTimeoutActionLockAllowed
+                ? _vaultTimeoutActionOptions.Select(o => CreateSelectableOption(o.Key, _vaultTimeoutActionDisplayValue == o.Key)).ToArray()
+                : _vaultTimeoutActionOptions.Where(o => o.Value == VaultTimeoutAction.Logout).Select(v => ToSelectedOption(v.Key)).ToArray();
+
             var selection = await Page.DisplayActionSheet(AppResources.VaultTimeoutAction,
                 AppResources.Cancel, null, options);
             if (selection == null || selection == AppResources.Cancel)
@@ -437,19 +452,20 @@ namespace Bit.App.Pages
 
                     var kdfConfig = await _stateService.GetActiveUserCustomDataAsync(a => new KdfConfig(a?.Profile));
                     var email = await _stateService.GetEmailAsync();
-                    var pinKey = await _cryptoService.MakePinKeyAysnc(pin, email, kdfConfig);
+                    var pinKey = await _cryptoService.MakePinKeyAsync(pin, email, kdfConfig);
-                    var key = await _cryptoService.GetKeyAsync();
+                    var userKey = await _cryptoService.GetUserKeyAsync();
-                    var pinProtectedKey = await _cryptoService.EncryptAsync(key.Key, pinKey);
+                    var pinProtectedKey = await _cryptoService.EncryptAsync(userKey.Key, pinKey);
+
+                    var encPin = await _cryptoService.EncryptAsync(pin);
+                    await _stateService.SetProtectedPinAsync(encPin.EncryptedString);
 
                     if (masterPassOnRestart)
                     {
-                        var encPin = await _cryptoService.EncryptAsync(pin);
+                        await _stateService.SetUserKeyPinEphemeralAsync(pinProtectedKey);
-                        await _stateService.SetProtectedPinAsync(encPin.EncryptedString);
-                        await _stateService.SetPinProtectedKeyAsync(pinProtectedKey);
                     }
                     else
                     {
-                        await _stateService.SetPinProtectedAsync(pinProtectedKey.EncryptedString);
+                        await _stateService.SetUserKeyPinAsync(pinProtectedKey);
                     }
                 }
                 else
@@ -459,7 +475,6 @@ namespace Bit.App.Pages
             }
             if (!_pin)
             {
-                await _cryptoService.ClearPinProtectedKeyAsync();
                 await _vaultTimeoutService.ClearAsync();
             }
             BuildList();
@@ -489,9 +504,10 @@ namespace Bit.App.Pages
             else
             {
                 await _stateService.SetBiometricUnlockAsync(null);
+                await UpdateVaultTimeoutActionIfNeededAsync();
             }
             await _stateService.SetBiometricLockedAsync(false);
-            await _cryptoService.ToggleKeyAsync();
+            await _cryptoService.ToggleKeysAsync();
             BuildList();
         }
 
@@ -835,9 +851,11 @@ namespace Bit.App.Pages
             return _vaultTimeoutOptions.FirstOrDefault(o => o.Key == key).Value;
         }
 
-        private string CreateSelectableOption(string option, bool selected) => selected ? $"✓ {option}" : option;
+        private string CreateSelectableOption(string option, bool selected) => selected ? ToSelectedOption(option) : option;
 
-        private bool CompareSelection(string selection, string compareTo) => selection == compareTo || selection == $"✓ {compareTo}";
+        private bool CompareSelection(string selection, string compareTo) => selection == compareTo || selection == ToSelectedOption(compareTo);
+
+        private string ToSelectedOption(string option) => $"✓ {option}";
 
         public async Task SetScreenCaptureAllowedAsync()
         {
@@ -869,5 +887,17 @@ namespace Bit.App.Pages
             await _watchDeviceService.SetShouldConnectToWatchAsync(_shouldConnectToWatch);
             BuildList();
         }
+
+        private async Task UpdateVaultTimeoutActionIfNeededAsync()
+        {
+            if (IsVaultTimeoutActionLockAllowed)
+            {
+                return;
+            }
+
+            _vaultTimeoutActionDisplayValue = _vaultTimeoutActionOptions.First(o => o.Value == VaultTimeoutAction.Logout).Key;
+            await _vaultTimeoutService.SetVaultTimeoutOptionsAsync(_vaultTimeout, VaultTimeoutAction.Logout);
+            _deviceActionService.Toast(AppResources.VaultTimeoutActionChangedToLogOut);
+        }
     }
 }

src/App/Pages/Vault/AttachmentsPageViewModel.cs

@@ -74,7 +74,7 @@ namespace Bit.App.Pages
             _cipherDomain = await _cipherService.GetAsync(CipherId);
             Cipher = await _cipherDomain.DecryptAsync();
             LoadAttachments();
-            _hasUpdatedKey = await _cryptoService.HasEncKeyAsync();
+            _hasUpdatedKey = await _cryptoService.HasUserKeyAsync();
             var canAccessPremium = await _stateService.CanAccessPremiumAsync();
             _canAccessAttachments = canAccessPremium || Cipher.OrganizationId != null;
             if (!_canAccessAttachments)

src/App/Resources/AppResources.Designer.cs

@@ -418,6 +418,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Admin approval requested.
+        /// </summary>
+        public static string AdminApprovalRequested {
+            get {
+                return ResourceManager.GetString("AdminApprovalRequested", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to All.
         /// </summary>
@@ -562,6 +571,24 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Approve with master password.
+        /// </summary>
+        public static string ApproveWithMasterPassword {
+            get {
+                return ResourceManager.GetString("ApproveWithMasterPassword", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Approve with my other device.
+        /// </summary>
+        public static string ApproveWithMyOtherDevice {
+            get {
+                return ResourceManager.GetString("ApproveWithMyOtherDevice", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to April.
         /// </summary>
@@ -3658,6 +3685,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Logged in!.
+        /// </summary>
+        public static string LoggedIn {
+            get {
+                return ResourceManager.GetString("LoggedIn", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Logged in as {0} on {1}..
         /// </summary>
@@ -3676,6 +3712,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Logging in as {0}.
+        /// </summary>
+        public static string LoggingInAsX {
+            get {
+                return ResourceManager.GetString("LoggingInAsX", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Logging in as {0} on {1}.
         /// </summary>
@@ -5273,6 +5318,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Remember this device.
+        /// </summary>
+        public static string RememberThisDevice {
+            get {
+                return ResourceManager.GetString("RememberThisDevice", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Remove.
         /// </summary>
@@ -5345,6 +5399,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Request admin approval.
+        /// </summary>
+        public static string RequestAdminApproval {
+            get {
+                return ResourceManager.GetString("RequestAdminApproval", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Request one-time password.
         /// </summary>
@@ -6353,6 +6416,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Trouble logging in?.
+        /// </summary>
+        public static string TroubleLoggingIn {
+            get {
+                return ResourceManager.GetString("TroubleLoggingIn", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Try again.
         /// </summary>
@@ -6362,6 +6434,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Turn off using a public device.
+        /// </summary>
+        public static string TurnOffUsingPublicDevice {
+            get {
+                return ResourceManager.GetString("TurnOffUsingPublicDevice", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to 20 seconds.
         /// </summary>
@@ -6893,6 +6974,15 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Vault timeout action changed to log out.
+        /// </summary>
+        public static string VaultTimeoutActionChangedToLogOut {
+            get {
+                return ResourceManager.GetString("VaultTimeoutActionChangedToLogOut", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Your organization policies have set your vault timeout action to {0}..
         /// </summary>
@@ -7262,6 +7352,24 @@ namespace Bit.App.Resources {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Your request has been sent to your admin..
+        /// </summary>
+        public static string YourRequestHasBeenSentToYourAdmin {
+            get {
+                return ResourceManager.GetString("YourRequestHasBeenSentToYourAdmin", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to You will be notified once approved. .
+        /// </summary>
+        public static string YouWillBeNotifiedOnceApproved {
+            get {
+                return ResourceManager.GetString("YouWillBeNotifiedOnceApproved", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to To continue, hold your YubiKey NEO against the back of the device or insert your YubiKey into your device&apos;s USB port, then touch its button..
         /// </summary>

src/App/Resources/AppResources.resx

@@ -2628,6 +2628,24 @@ Do you want to switch to this account?</value>
   <data name="CurrentMasterPassword" xml:space="preserve">
     <value>Current master password</value>
   </data>
+  <data name="LoggedIn" xml:space="preserve">
+    <value>Logged in!</value>
+  </data>
+  <data name="ApproveWithMyOtherDevice" xml:space="preserve">
+    <value>Approve with my other device</value>
+  </data>
+  <data name="RequestAdminApproval" xml:space="preserve">
+    <value>Request admin approval</value>
+  </data>
+  <data name="ApproveWithMasterPassword" xml:space="preserve">
+    <value>Approve with master password</value>
+  </data>
+  <data name="TurnOffUsingPublicDevice" xml:space="preserve">
+    <value>Turn off using a public device</value>
+  </data>
+  <data name="RememberThisDevice" xml:space="preserve">
+    <value>Remember this device</value>
+  </data>
   <data name="MasterPasswordRePromptHelp" xml:space="preserve">
     <value>Master password re-prompt help</value>
   </data>
@@ -2640,6 +2658,24 @@ Do you want to switch to this account?</value>
   <data name="InvalidAPIToken" xml:space="preserve">
     <value>Invalid API token</value>
   </data>
+  <data name="AdminApprovalRequested" xml:space="preserve">
+    <value>Admin approval requested</value>
+  </data>
+  <data name="YourRequestHasBeenSentToYourAdmin" xml:space="preserve">
+    <value>Your request has been sent to your admin.</value>
+  </data>
+  <data name="YouWillBeNotifiedOnceApproved" xml:space="preserve">
+    <value>You will be notified once approved. </value>
+  </data>
+  <data name="TroubleLoggingIn" xml:space="preserve">
+    <value>Trouble logging in?</value>
+  </data>
+  <data name="LoggingInAsX" xml:space="preserve">
+    <value>Logging in as {0}</value>
+  </data>
+  <data name="VaultTimeoutActionChangedToLogOut" xml:space="preserve">
+    <value>Vault timeout action changed to log out</value>
+  </data>
   <data name="BlockAutoFill" xml:space="preserve">
     <value>Block auto-fill</value>
   </data>

src/App/Services/MobilePasswordRepromptService.cs

@@ -38,7 +38,7 @@ namespace Bit.App.Services
                 return false;
             };
 
-            return await _cryptoService.CompareAndUpdateKeyHashAsync(password, null);
+            return await _cryptoService.CompareAndUpdatePasswordHashAsync(password, null);
         }
 
         public async Task<bool> Enabled()

src/Core/Abstractions/IApiService.cs

@@ -4,6 +4,7 @@ using System.Net;
 using System.Net.Http;
 using System.Threading;
 using System.Threading.Tasks;
+using Bit.Core.Enums;
 using Bit.Core.Models.Domain;
 using Bit.Core.Models.Request;
 using Bit.Core.Models.Response;
@@ -70,7 +71,7 @@ namespace Bit.Core.Abstractions
         Task<OrganizationAutoEnrollStatusResponse> GetOrganizationAutoEnrollStatusAsync(string identifier);
         Task PutOrganizationUserResetPasswordEnrollmentAsync(string orgId, string userId,
             OrganizationUserResetPasswordEnrollmentRequest request);
-        Task<KeyConnectorUserKeyResponse> GetUserKeyFromKeyConnector(string keyConnectorUrl);
+        Task<KeyConnectorUserKeyResponse> GetMasterKeyFromKeyConnector(string keyConnectorUrl);
         Task PostUserKeyToKeyConnector(string keyConnectorUrl, KeyConnectorUserKeyRequest request);
         Task PostSetKeyConnectorKey(SetKeyConnectorKeyRequest request);
         Task PostConvertToKeyConnector();
@@ -90,9 +91,12 @@ namespace Bit.Core.Abstractions
         Task<PasswordlessLoginResponse> GetAuthRequestAsync(string id);
         Task<PasswordlessLoginResponse> GetAuthResponseAsync(string id, string accessCode);
         Task<PasswordlessLoginResponse> PutAuthRequestAsync(string id, string key, string masterPasswordHash, string deviceIdentifier, bool requestApproved);
-        Task<PasswordlessLoginResponse> PostCreateRequestAsync(PasswordlessCreateLoginRequest passwordlessCreateLoginRequest);
+        Task<PasswordlessLoginResponse> PostCreateRequestAsync(PasswordlessCreateLoginRequest passwordlessCreateLoginRequest, AuthRequestType authRequestType);
         Task<bool> GetKnownDeviceAsync(string email, string deviceIdentifier);
+        Task<DeviceResponse> GetDeviceByIdentifierAsync(string deviceIdentifier);
+        Task<DeviceResponse> UpdateTrustedDeviceKeysAsync(string deviceIdentifier, TrustedDeviceKeysRequest deviceRequest);
         Task<OrganizationDomainSsoDetailsResponse> GetOrgDomainSsoDetailsAsync(string email);
+        Task<bool> GetDevicesExistenceByTypes(DeviceType[] deviceTypes);
         Task<ConfigResponse> GetConfigsAsync();
         Task<string> GetFastmailAccountIdAsync(string apiKey);
     }

src/Core/Abstractions/IAuthService.cs

@@ -32,9 +32,12 @@ namespace Bit.Core.Abstractions
         Task<List<PasswordlessLoginResponse>> GetPasswordlessLoginRequestsAsync();
         Task<List<PasswordlessLoginResponse>> GetActivePasswordlessLoginRequestsAsync();
         Task<PasswordlessLoginResponse> GetPasswordlessLoginRequestByIdAsync(string id);
-        Task<PasswordlessLoginResponse> GetPasswordlessLoginResponseAsync(string id, string accessCode);
+        /// <summary>
+        /// Gets a passwordless login request by <paramref name="id"/> and <paramref name="accessCode"/>. No authentication required.
+        /// </summary>
+        Task<PasswordlessLoginResponse> GetPasswordlessLoginResquestAsync(string id, string accessCode);
         Task<PasswordlessLoginResponse> PasswordlessLoginAsync(string id, string pubKey, bool requestApproved);
-        Task<PasswordlessLoginResponse> PasswordlessCreateLoginRequestAsync(string email);
+        Task<PasswordlessLoginResponse> PasswordlessCreateLoginRequestAsync(string email, AuthRequestType authRequestType);
 
         void LogOut(Action callback);
         void Init();

src/Core/Abstractions/ICryptoService.cs

@@ -9,49 +9,54 @@ namespace Bit.Core.Abstractions
 {
     public interface ICryptoService
     {
-        Task ClearEncKeyAsync(bool memoryOnly = false, string userId = null);
-        Task ClearKeyAsync(string userId = null);
-        Task ClearKeyHashAsync(string userId = null);
-        Task ClearKeyPairAsync(bool memoryOnly = false, string userId = null);
-        Task ClearKeysAsync(string userId = null);
-        Task ClearOrgKeysAsync(bool memoryOnly = false, string userId = null);
-        Task ClearPinProtectedKeyAsync(string userId = null);
         void ClearCache();
+        Task ToggleKeysAsync();
+        Task SetUserKeyAsync(UserKey userKey, string userId = null);
+        Task<UserKey> GetUserKeyAsync(string userId = null);
+        Task<UserKey> GetUserKeyWithLegacySupportAsync(string userId = null);
+        Task<bool> HasUserKeyAsync(string userId = null);
+        Task<bool> HasEncryptedUserKeyAsync(string userId = null);
+        Task<UserKey> MakeUserKeyAsync();
+        Task ClearUserKeyAsync(string userId = null);
+        Task SetMasterKeyEncryptedUserKeyAsync(string value, string userId = null);
+        Task SetMasterKeyAsync(MasterKey masterKey, string userId = null);
+        Task<MasterKey> GetMasterKeyAsync(string userId = null);
+        Task<MasterKey> MakeMasterKeyAsync(string password, string email, KdfConfig kdfConfig);
+        Task ClearMasterKeyAsync(string userId = null);
+        Task<Tuple<UserKey, EncString>> EncryptUserKeyWithMasterKeyAsync(MasterKey masterKey, UserKey userKey = null);
+        Task<UserKey> DecryptUserKeyWithMasterKeyAsync(MasterKey masterKey, EncString encUserKey = null, string userId = null);
+        Task<Tuple<SymmetricCryptoKey, EncString>> MakeDataEncKeyAsync(UserKey key);
+        Task<Tuple<SymmetricCryptoKey, EncString>> MakeDataEncKeyAsync(OrgKey key);
+        Task<string> HashPasswordAsync(string password, SymmetricCryptoKey key, HashPurpose hashPurpose = HashPurpose.ServerAuthorization);
+        Task SetPasswordHashAsync(string keyHash);
+        Task<string> GetPasswordHashAsync();
+        Task ClearPasswordHashAsync(string userId = null);
+        Task<bool> CompareAndUpdatePasswordHashAsync(string masterPassword, MasterKey key);
+        Task SetOrgKeysAsync(IEnumerable<ProfileOrganizationResponse> orgs);
+        Task<OrgKey> GetOrgKeyAsync(string orgId);
+        Task<Dictionary<string, OrgKey>> GetOrgKeysAsync();
+        Task ClearOrgKeysAsync(bool memoryOnly = false, string userId = null);
+        Task<byte[]> GetPublicKeyAsync();
+        Task SetPrivateKeyAsync(string encPrivateKey);
+        Task<byte[]> GetPrivateKeyAsync();
+        Task<List<string>> GetFingerprintAsync(string userId, byte[] publicKey = null);
+        Task<Tuple<string, EncString>> MakeKeyPairAsync(SymmetricCryptoKey key = null);
+        Task ClearKeyPairAsync(bool memoryOnly = false, string userId = null);
+        Task<PinKey> MakePinKeyAsync(string pin, string salt, KdfConfig config);
+        Task ClearPinKeysAsync(string userId = null);
+        Task<UserKey> DecryptUserKeyWithPinAsync(string pin, string salt, KdfConfig kdfConfig, EncString pinProtectedUserKey = null);
+        Task<MasterKey> DecryptMasterKeyWithPinAsync(string pin, string salt, KdfConfig kdfConfig, EncString pinProtectedMasterKey = null);
+        Task<SymmetricCryptoKey> MakeSendKeyAsync(byte[] keyMaterial);
+        Task<EncString> RsaEncryptAsync(byte[] data, byte[] publicKey = null);
+        Task<byte[]> RsaDecryptAsync(string encValue, byte[] privateKey = null);
+        Task<int> RandomNumberAsync(int min, int max);
+        Task<string> RandomStringAsync(int length);
         Task<byte[]> DecryptFromBytesAsync(byte[] encBytes, SymmetricCryptoKey key);
         Task<byte[]> DecryptToBytesAsync(EncString encString, SymmetricCryptoKey key = null);
         Task<string> DecryptToUtf8Async(EncString encString, SymmetricCryptoKey key = null);
         Task<EncString> EncryptAsync(byte[] plainValue, SymmetricCryptoKey key = null);
         Task<EncString> EncryptAsync(string plainValue, SymmetricCryptoKey key = null);
         Task<EncByteArray> EncryptToBytesAsync(byte[] plainValue, SymmetricCryptoKey key = null);
-        Task<SymmetricCryptoKey> GetEncKeyAsync(SymmetricCryptoKey key = null);
+        Task<UserKey> DecryptAndMigrateOldPinKeyAsync(bool masterPasswordOnRestart, string pin, string email, KdfConfig kdfConfig, EncString oldPinKey);
-        Task<List<string>> GetFingerprintAsync(string userId, byte[] publicKey = null);
-        Task<SymmetricCryptoKey> GetKeyAsync(string userId = null);
-        Task<string> GetKeyHashAsync();
-        Task<SymmetricCryptoKey> GetOrgKeyAsync(string orgId);
-        Task<Dictionary<string, SymmetricCryptoKey>> GetOrgKeysAsync();
-        Task<byte[]> GetPrivateKeyAsync();
-        Task<byte[]> GetPublicKeyAsync();
-        Task<bool> CompareAndUpdateKeyHashAsync(string masterPassword, SymmetricCryptoKey key);
-        Task<bool> HasEncKeyAsync();
-        Task<string> HashPasswordAsync(string password, SymmetricCryptoKey key, HashPurpose hashPurpose = HashPurpose.ServerAuthorization);
-        Task<bool> HasKeyAsync(string userId = null);
-        Task<Tuple<SymmetricCryptoKey, EncString>> MakeEncKeyAsync(SymmetricCryptoKey key);
-        Task<SymmetricCryptoKey> MakeKeyAsync(string password, string salt, KdfConfig config);
-        Task<SymmetricCryptoKey> MakeKeyFromPinAsync(string pin, string salt, KdfConfig config, EncString protectedKeyEs = null);
-        Task<Tuple<string, EncString>> MakeKeyPairAsync(SymmetricCryptoKey key = null);
-        Task<SymmetricCryptoKey> MakePinKeyAysnc(string pin, string salt, KdfConfig config);
-        Task<Tuple<EncString, SymmetricCryptoKey>> MakeShareKeyAsync();
-        Task<SymmetricCryptoKey> MakeSendKeyAsync(byte[] keyMaterial);
-        Task<int> RandomNumberAsync(int min, int max);
-        Task<string> RandomStringAsync(int length);
-        Task<Tuple<SymmetricCryptoKey, EncString>> RemakeEncKeyAsync(SymmetricCryptoKey key);
-        Task<EncString> RsaEncryptAsync(byte[] data, byte[] publicKey = null);
-        Task<byte[]> RsaDecryptAsync(string encValue, byte[] privateKey = null);
-        Task SetEncKeyAsync(string encKey);
-        Task SetEncPrivateKeyAsync(string encPrivateKey);
-        Task SetKeyAsync(SymmetricCryptoKey key);
-        Task SetKeyHashAsync(string keyHash);
-        Task SetOrgKeysAsync(IEnumerable<ProfileOrganizationResponse> orgs);
-        Task ToggleKeyAsync();
     }
 }

src/Core/Abstractions/IDeviceTrustCryptoService.cs

@@ -0,0 +1,16 @@
+using System.Threading.Tasks;
+using Bit.Core.Models.Domain;
+
+namespace Bit.Core.Abstractions
+{
+    public interface IDeviceTrustCryptoService
+    {
+        Task<SymmetricCryptoKey> GetDeviceKeyAsync();
+        Task<DeviceResponse> TrustDeviceAsync();
+        Task<DeviceResponse> TrustDeviceIfNeededAsync();
+        Task<bool> GetShouldTrustDeviceAsync();
+        Task SetShouldTrustDeviceAsync(bool value);
+        Task<UserKey> DecryptUserKeyWithDeviceKeyAsync(string encryptedDevicePrivateKey, string encryptedUserKey);
+        Task<bool> IsDeviceTrustedAsync();
+    }
+}

src/Core/Abstractions/IStateService.cs

@@ -13,6 +13,12 @@ namespace Bit.Core.Abstractions
     public interface IStateService
     {
         List<AccountView> AccountViews { get; }
+        Task<UserKey> GetUserKeyAsync(string userId = null);
+        Task SetUserKeyAsync(UserKey value, string userId = null);
+        Task<MasterKey> GetMasterKeyAsync(string userId = null);
+        Task SetMasterKeyAsync(MasterKey value, string userId = null);
+        Task<string> GetUserKeyMasterKeyAsync(string userId = null);
+        Task SetUserKeyMasterKeyAsync(string value, string userId = null);
         Task<string> GetActiveUserIdAsync();
         Task<string> GetActiveUserEmailAsync();
         Task<T> GetActiveUserCustomDataAsync<T>(Func<Account, T> dataMapper);
@@ -36,26 +42,30 @@ namespace Bit.Core.Abstractions
         Task<bool> IsAccountBiometricIntegrityValidAsync(string bioIntegritySrcKey, string userId = null);
         Task SetAccountBiometricIntegrityValidAsync(string bioIntegritySrcKey, string userId = null);
         Task<bool> CanAccessPremiumAsync(string userId = null);
-        Task SetPersonalPremiumAsync(bool value, string userId = null);
         Task<string> GetProtectedPinAsync(string userId = null);
+        Task SetPersonalPremiumAsync(bool value, string userId = null);
+        Task<EncString> GetUserKeyPinAsync(string userId = null);
+        Task SetUserKeyPinAsync(EncString value, string userId = null);
+        Task<EncString> GetUserKeyPinEphemeralAsync(string userId = null);
+        Task SetUserKeyPinEphemeralAsync(EncString value, string userId = null);
         Task SetProtectedPinAsync(string value, string userId = null);
+        [Obsolete("Use GetUserKeyPinAsync instead, left for migration purposes")]
         Task<string> GetPinProtectedAsync(string userId = null);
+        [Obsolete("Use SetUserKeyPinAsync instead")]
         Task SetPinProtectedAsync(string value, string userId = null);
+        [Obsolete("Use GetUserKeyPinEphemeralAsync instead, left for migration purposes")]
         Task<EncString> GetPinProtectedKeyAsync(string userId = null);
+        [Obsolete("Use SetUserKeyPinEphemeralAsync instead")]
         Task SetPinProtectedKeyAsync(EncString value, string userId = null);
         Task SetKdfConfigurationAsync(KdfConfig config, string userId = null);
-        Task<string> GetKeyEncryptedAsync(string userId = null);
-        Task SetKeyEncryptedAsync(string value, string userId = null);
-        Task<SymmetricCryptoKey> GetKeyDecryptedAsync(string userId = null);
-        Task SetKeyDecryptedAsync(SymmetricCryptoKey value, string userId = null);
         Task<string> GetKeyHashAsync(string userId = null);
         Task SetKeyHashAsync(string value, string userId = null);
-        Task<string> GetEncKeyEncryptedAsync(string userId = null);
-        Task SetEncKeyEncryptedAsync(string value, string userId = null);
         Task<Dictionary<string, string>> GetOrgKeysEncryptedAsync(string userId = null);
         Task SetOrgKeysEncryptedAsync(Dictionary<string, string> value, string userId = null);
         Task<string> GetPrivateKeyEncryptedAsync(string userId = null);
         Task SetPrivateKeyEncryptedAsync(string value, string userId = null);
+        Task<SymmetricCryptoKey> GetDeviceKeyAsync(string userId = null);
+        Task SetDeviceKeyAsync(SymmetricCryptoKey value, string userId = null);
         Task<List<string>> GetAutofillBlacklistedUrisAsync(string userId = null);
         Task SetAutofillBlacklistedUrisAsync(List<string> value, string userId = null);
         Task<bool?> GetAutofillTileAddedAsync();
@@ -172,9 +182,26 @@ namespace Bit.Core.Abstractions
         Task<string> GetAvatarColorAsync(string userId = null);
         Task<string> GetPreLoginEmailAsync();
         Task SetPreLoginEmailAsync(string value);
+        Task<AccountDecryptionOptions> GetAccountDecryptionOptions(string userId = null);
+        Task<PendingAdminAuthRequest> GetPendingAdminAuthRequestAsync(string userId = null);
+        Task SetPendingAdminAuthRequestAsync(PendingAdminAuthRequest value, string userId = null);
         string GetLocale();
         void SetLocale(string locale);
         ConfigResponse GetConfigs();
         void SetConfigs(ConfigResponse value);
+        Task<bool> GetShouldTrustDeviceAsync();
+        Task SetShouldTrustDeviceAsync(bool value);
+        [Obsolete("Use GetUserKeyMasterKey instead")]
+        Task<string> GetEncKeyEncryptedAsync(string userId = null);
+        [Obsolete("Use SetUserKeyMasterKey instead")]
+        Task SetEncKeyEncryptedAsync(string value, string userId = null);
+        [Obsolete]
+        Task<string> GetKeyEncryptedAsync(string userId = null);
+        [Obsolete]
+        Task SetKeyEncryptedAsync(string value, string userId = null);
+        [Obsolete("Use GetMasterKey instead")]
+        Task<SymmetricCryptoKey> GetKeyDecryptedAsync(string userId = null);
+        [Obsolete("Use GetMasterKey instead")]
+        Task SetKeyDecryptedAsync(SymmetricCryptoKey value, string userId = null);
     }
 }

src/Core/Abstractions/IVaultTimeoutService.cs

@@ -1,6 +1,7 @@
 using System;
 using System.Threading.Tasks;
 using Bit.Core.Enums;
+using Bit.Core.Services;
 
 namespace Bit.Core.Abstractions
 {
@@ -16,7 +17,7 @@ namespace Bit.Core.Abstractions
         Task<bool> ShouldLockAsync(string userId = null);
         Task<bool> IsLoggedOutByTimeoutAsync(string userId = null);
         Task<bool> ShouldLogOutByTimeoutAsync(string userId = null);
-        Task<Tuple<bool, bool>> IsPinLockSetAsync(string userId = null);
+        Task<PinLockEnum> IsPinLockSetAsync(string userId = null);
         Task<bool> IsBiometricLockSetAsync(string userId = null);
         Task LockAsync(bool allowSoftLock = false, bool userInitiated = false, string userId = null);
         Task LogOutAsync(bool userInitiated = true, string userId = null);

src/Core/Constants.cs

@@ -1,4 +1,6 @@
-namespace Bit.Core
+using System;
+
+namespace Bit.Core
 {
     public static class Constants
     {
@@ -53,6 +55,7 @@
         public const string AppLocaleKey = "appLocale";
         public const string ClearSensitiveFields = "clearSensitiveFields";
         public const string ForceUpdatePassword = "forceUpdatePassword";
+        public const string ShouldTrustDevice = "shouldTrustDevice";
         public const int SelectFileRequestCode = 42;
         public const int SelectFilePermissionRequestCode = 43;
         public const int SaveFileRequestCode = 44;
@@ -79,6 +82,7 @@
 
         public static string VaultTimeoutKey(string userId) => $"vaultTimeout_{userId}";
         public static string VaultTimeoutActionKey(string userId) => $"vaultTimeoutAction_{userId}";
+        public static string UserKeyKey(string userId) => $"userKey_{userId}";
         public static string CiphersKey(string userId) => $"ciphers_{userId}";
         public static string FoldersKey(string userId) => $"folders_{userId}";
         public static string CollectionsKey(string userId) => $"collections_{userId}";
@@ -87,12 +91,11 @@
         public static string NeverDomainsKey(string userId) => $"neverDomains_{userId}";
         public static string SendsKey(string userId) => $"sends_{userId}";
         public static string PoliciesKey(string userId) => $"policies_{userId}";
-        public static string KeyKey(string userId) => $"key_{userId}";
         public static string EncOrgKeysKey(string userId) => $"encOrgKeys_{userId}";
         public static string EncPrivateKeyKey(string userId) => $"encPrivateKey_{userId}";
-        public static string EncKeyKey(string userId) => $"encKey_{userId}";
+        public static string DeviceKeyKey(string userId) => $"deviceKey_{userId}";
         public static string KeyHashKey(string userId) => $"keyHash_{userId}";
-        public static string PinProtectedKey(string userId) => $"pinProtectedKey_{userId}";
+        public static string UserKeyPinKey(string userId) => $"userKeyPin_{userId}";
         public static string PassGenOptionsKey(string userId) => $"passwordGenerationOptions_{userId}";
         public static string PassGenHistoryKey(string userId) => $"generatedPasswordHistory_{userId}";
         public static string TwoFactorTokenKey(string email) => $"twoFactorToken_{email}";
@@ -121,5 +124,12 @@
         public static string PushCurrentTokenKey(string userId) => $"pushCurrentToken_{userId}";
         public static string ShouldConnectToWatchKey(string userId) => $"shouldConnectToWatch_{userId}";
         public static string ScreenCaptureAllowedKey(string userId) => $"screenCaptureAllowed_{userId}";
+        public static string PendingAdminAuthRequest(string userId) => $"pendingAdminAuthRequest_{userId}";
+        [Obsolete]
+        public static string KeyKey(string userId) => $"key_{userId}";
+        [Obsolete]
+        public static string EncKeyKey(string userId) => $"encKey_{userId}";
+        [Obsolete]
+        public static string PinProtectedKey(string userId) => $"pinProtectedKey_{userId}";
     }
 }

src/Core/Enums/AuthRequestType.cs

@@ -0,0 +1,11 @@
+using System;
+namespace Bit.Core.Enums
+{
+    public enum AuthRequestType : byte
+    {
+        AuthenticateAndUnlock = 0,
+        Unlock = 1,
+        AdminApproval = 2
+    }
+}
+

src/Core/Enums/DeviceType.cs

@@ -1,4 +1,7 @@
-namespace Bit.Core.Enums
+using System.Collections.Generic;
+using System.Linq;
+
+namespace Bit.Core.Enums
 {
     public enum DeviceType : byte
     {
@@ -24,4 +27,24 @@
         VivaldiExtension = 19,
         SafariExtension = 20
     }
+
+    public static class DeviceTypeExtensions
+    {
+        public static List<DeviceType> GetMobileTypes() => new List<DeviceType>
+            {
+                DeviceType.Android,
+                DeviceType.AndroidAmazon,
+                DeviceType.iOS
+            };
+
+        public static List<DeviceType> GetDesktopTypes() => new List<DeviceType>
+            {
+                DeviceType.WindowsDesktop,
+                DeviceType.MacOsDesktop,
+                DeviceType.LinuxDesktop,
+                DeviceType.UWP,
+            };
+
+        public static List<DeviceType> GetDesktopAndMobileTypes() => GetMobileTypes().Concat(GetDesktopTypes()).ToList();
+    }
 }

src/Core/Models/Domain/Account.cs

@@ -53,6 +53,7 @@ namespace Bit.Core.Models.Domain
                 HasPremiumPersonally = copy.HasPremiumPersonally;
                 AvatarColor = copy.AvatarColor;
                 ForcePasswordResetReason = copy.ForcePasswordResetReason;
+                UserDecryptionOptions = copy.UserDecryptionOptions;
             }
 
             public string UserId;
@@ -68,6 +69,7 @@ namespace Bit.Core.Models.Domain
             public bool? EmailVerified;
             public bool? HasPremiumPersonally;
             public ForcePasswordResetReason? ForcePasswordResetReason;
+            public AccountDecryptionOptions UserDecryptionOptions;
         }
 
         public class AccountTokens
@@ -117,9 +119,14 @@ namespace Bit.Core.Models.Domain
 
         public class AccountVolatileData
         {
-            public SymmetricCryptoKey Key;
+            public UserKey UserKey;
-            public EncString PinProtectedKey;
+            public MasterKey MasterKey;
+            public EncString UserKeyPinEphemeral;
             public bool? BiometricLocked;
+            [Obsolete("Jul 6 2023: Key has been deprecated. We will use the User Key in the future. It remains here for migration during app upgrade.")]
+            public SymmetricCryptoKey Key;
+            [Obsolete("Jul 6 2023: PinProtectedKey has been deprecated in favor of UserKeyPinEphemeral. It remains here for migration during app upgrade.")]
+            public EncString PinProtectedKey;
         }
     }
 }

src/Core/Models/Domain/AccountDecryptionOptions.cs

@@ -0,0 +1,25 @@
+using System;
+namespace Bit.Core.Models.Domain
+{
+    public class AccountDecryptionOptions
+    {
+        public bool HasMasterPassword { get; set; }
+        public TrustedDeviceOption TrustedDeviceOption { get; set; }
+        public KeyConnectorOption KeyConnectorOption { get; set; }
+    }
+
+    public class TrustedDeviceOption
+    {
+        public bool HasAdminApproval { get; set; }
+        public bool HasLoginApprovingDevice { get; set; }
+        public bool HasManageResetPasswordPermission { get; set; }
+        public string EncryptedPrivateKey { get; set; }
+        public string EncryptedUserKey { get; set; }
+    }
+
+    public class KeyConnectorOption
+    {
+        public string KeyConnectorUrl { get; set; }
+    }
+}
+

src/Core/Models/Domain/PendingAdminAuthRequest.cs

@@ -0,0 +1,10 @@
+using System;
+namespace Bit.Core.Models.Domain
+{
+    public class PendingAdminAuthRequest
+    {
+        public string Id { get; set; }
+        public byte[] PrivateKey { get; set; }
+    }
+}
+

src/Core/Models/Domain/SymmetricCryptoKey.cs

@@ -74,4 +74,32 @@ namespace Bit.Core.Models.Domain
         public string EncKeyB64 { get; set; }
         public string MacKeyB64 { get; set; }
     }
+
+    public class UserKey : SymmetricCryptoKey
+    {
+        public UserKey(byte[] key, EncryptionType? encType = null)
+            : base(key, encType)
+        { }
+    }
+
+    public class MasterKey : SymmetricCryptoKey
+    {
+        public MasterKey(byte[] key, EncryptionType? encType = null)
+            : base(key, encType)
+        { }
+    }
+
+    public class PinKey : SymmetricCryptoKey
+    {
+        public PinKey(byte[] key, EncryptionType? encType = null)
+            : base(key, encType)
+        { }
+    }
+
+    public class OrgKey : SymmetricCryptoKey
+    {
+        public OrgKey(byte[] key, EncryptionType? encType = null)
+            : base(key, encType)
+        { }
+    }
 }

src/Core/Models/Request/PasswordlessCreateLoginRequest.cs

@@ -1,4 +1,6 @@
 using System;
+using Bit.Core.Enums;
+
 namespace Bit.Core.Models.Request
 {
     public class PasswordlessCreateLoginRequest
@@ -25,10 +27,4 @@ namespace Bit.Core.Models.Request
 
         public string FingerprintPhrase { get; set; }
     }
-
-    public enum AuthRequestType : byte
-    {
-        AuthenticateAndUnlock = 0,
-        Unlock = 1
-    }
 }

src/Core/Models/Request/TrustedDeviceKeysRequest.cs

@@ -0,0 +1,10 @@
+
+namespace Bit.Core.Models.Request
+{
+    public class TrustedDeviceKeysRequest
+    {
+        public string EncryptedUserKey { get; set; }
+        public string EncryptedPublicKey { get; set; }
+        public string EncryptedPrivateKey { get; set; }
+    }
+}

src/Core/Models/Response/DeviceResponse.cs

@@ -0,0 +1,13 @@
+using Bit.Core.Enums;
+
+public class DeviceResponse
+{
+    public string Id { get; set; }
+    public string Name { get; set; }
+    public string Identifier { get; set; }
+    public DeviceType Type { get; set; }
+    public string CreationDate { get; set; }
+    public string EncryptedUserKey { get; set; }
+    public string EncryptedPublicKey { get; set; }
+    public string EncryptedPrivateKey { get; set; }
+}

src/Core/Models/Response/IdentityTokenResponse.cs

@@ -27,6 +27,7 @@ namespace Bit.Core.Models.Response
         public bool ForcePasswordReset { get; set; }
         public string KeyConnectorUrl { get; set; }
         public MasterPasswordPolicyOptions MasterPasswordPolicy { get; set; }
+        public AccountDecryptionOptions UserDecryptionOptions { get; set; }
         [JsonIgnore]
         public KdfConfig KdfConfig => new KdfConfig(Kdf, KdfIterations, KdfMemory, KdfParallelism);
     }

src/Core/Services/ApiService.cs

@@ -397,12 +397,38 @@ namespace Bit.Core.Services
 
         #region Device APIs
 
+
+        public Task<bool> GetKnownDeviceAsync(string email, string deviceIdentifier)
+        {
+            return SendAsync<object, bool>(HttpMethod.Get, "/devices/knowndevice", null, false, true, (message) =>
+            {
+                message.Headers.Add("X-Device-Identifier", deviceIdentifier);
+                message.Headers.Add("X-Request-Email", CoreHelpers.Base64UrlEncode(Encoding.UTF8.GetBytes(email)));
+            });
+        }
+
         public Task PutDeviceTokenAsync(string identifier, DeviceTokenRequest request)
         {
             return SendAsync<DeviceTokenRequest, object>(
                 HttpMethod.Put, $"/devices/identifier/{identifier}/token", request, true, false);
         }
 
+        public Task<bool> GetDevicesExistenceByTypes(DeviceType[] deviceTypes)
+        {
+            return SendAsync<DeviceType[], bool>(
+                HttpMethod.Post, "/devices/exist-by-types", deviceTypes, true, true);
+        }
+
+        public Task<DeviceResponse> GetDeviceByIdentifierAsync(string deviceIdentifier)
+        {
+            return SendAsync<object, DeviceResponse>(HttpMethod.Get, $"/devices/identifier/{deviceIdentifier}", null, true, true);
+        }
+
+        public Task<DeviceResponse> UpdateTrustedDeviceKeysAsync(string deviceIdentifier, TrustedDeviceKeysRequest trustedDeviceKeysRequest)
+        {
+            return SendAsync<TrustedDeviceKeysRequest, DeviceResponse>(HttpMethod.Put, $"/devices/{deviceIdentifier}/keys", trustedDeviceKeysRequest, true, true);
+        }
+
         #endregion
 
         #region Event APIs
@@ -485,7 +511,7 @@ namespace Bit.Core.Services
 
         #region Key Connector
 
-        public async Task<KeyConnectorUserKeyResponse> GetUserKeyFromKeyConnector(string keyConnectorUrl)
+        public async Task<KeyConnectorUserKeyResponse> GetMasterKeyFromKeyConnector(string keyConnectorUrl)
         {
             using (var requestMessage = new HttpRequestMessage())
             {
@@ -565,9 +591,9 @@ namespace Bit.Core.Services
             return SendAsync<object, PasswordlessLoginResponse>(HttpMethod.Get, $"/auth-requests/{id}/response?code={accessCode}", null, false, true);
         }
 
-        public Task<PasswordlessLoginResponse> PostCreateRequestAsync(PasswordlessCreateLoginRequest passwordlessCreateLoginRequest)
+        public Task<PasswordlessLoginResponse> PostCreateRequestAsync(PasswordlessCreateLoginRequest passwordlessCreateLoginRequest, AuthRequestType authRequestType)
         {
-            return SendAsync<object, PasswordlessLoginResponse>(HttpMethod.Post, $"/auth-requests", passwordlessCreateLoginRequest, false, true);
+            return SendAsync<object, PasswordlessLoginResponse>(HttpMethod.Post, authRequestType == AuthRequestType.AdminApproval ? "/auth-requests/admin-request" : "/auth-requests", passwordlessCreateLoginRequest, authRequestType == AuthRequestType.AdminApproval, true);
         }
 
         public Task<PasswordlessLoginResponse> PutAuthRequestAsync(string id, string encKey, string encMasterPasswordHash, string deviceIdentifier, bool requestApproved)
@@ -576,15 +602,6 @@ namespace Bit.Core.Services
             return SendAsync<object, PasswordlessLoginResponse>(HttpMethod.Put, $"/auth-requests/{id}", request, true, true);
         }
 
-        public Task<bool> GetKnownDeviceAsync(string email, string deviceIdentifier)
-        {
-            return SendAsync<object, bool>(HttpMethod.Get, "/devices/knowndevice", null, false, true, (message) =>
-            {
-                message.Headers.Add("X-Device-Identifier", deviceIdentifier);
-                message.Headers.Add("X-Request-Email", CoreHelpers.Base64UrlEncode(Encoding.UTF8.GetBytes(email)));
-            });
-        }
-
         #endregion
 
         #region Configs

src/Core/Services/AuthService.cs

@@ -27,10 +27,11 @@ namespace Bit.Core.Services
         private readonly IKeyConnectorService _keyConnectorService;
         private readonly IPasswordGenerationService _passwordGenerationService;
         private readonly IPolicyService _policyService;
+        private readonly IDeviceTrustCryptoService _deviceTrustCryptoService;
         private readonly bool _setCryptoKeys;
 
         private readonly LazyResolve<IWatchDeviceService> _watchDeviceService = new LazyResolve<IWatchDeviceService>();
-        private SymmetricCryptoKey _key;
+        private MasterKey _masterKey;
 
         private string _authedUserId;
         private MasterPasswordPolicyOptions _masterPasswordPolicy;
@@ -50,6 +51,7 @@ namespace Bit.Core.Services
             IKeyConnectorService keyConnectorService,
             IPasswordGenerationService passwordGenerationService,
             IPolicyService policyService,
+            IDeviceTrustCryptoService deviceTrustCryptoService,
             bool setCryptoKeys = true)
         {
             _cryptoService = cryptoService;
@@ -64,6 +66,7 @@ namespace Bit.Core.Services
             _keyConnectorService = keyConnectorService;
             _passwordGenerationService = passwordGenerationService;
             _policyService = policyService;
+            _deviceTrustCryptoService = deviceTrustCryptoService;
             _setCryptoKeys = setCryptoKeys;
 
             TwoFactorProviders = new Dictionary<TwoFactorProviderType, TwoFactorProvider>();
@@ -195,11 +198,34 @@ namespace Bit.Core.Services
             return !await _policyService.EvaluateMasterPassword(strength.Value, masterPassword, _masterPasswordPolicy);
         }
 
-        public async Task<AuthResult> LogInPasswordlessAsync(string email, string accessCode, string authRequestId, byte[] decryptionKey, string userKeyCiphered, string localHashedPasswordCiphered)
+        public async Task<AuthResult> LogInPasswordlessAsync(string email, string accessCode, string authRequestId, byte[] decryptionKey, string encryptedAuthRequestKey, string masterKeyHash)
         {
-            var decKey = await _cryptoService.RsaDecryptAsync(userKeyCiphered, decryptionKey);
+            var decryptedKey = await _cryptoService.RsaDecryptAsync(encryptedAuthRequestKey, decryptionKey);
-            var decPasswordHash = await _cryptoService.RsaDecryptAsync(localHashedPasswordCiphered, decryptionKey);
+
-            return await LogInHelperAsync(email, accessCode, Encoding.UTF8.GetString(decPasswordHash), null, null, null, new SymmetricCryptoKey(decKey), null, null,
+            // On SSO flow user is already AuthN
+            if (await _stateService.IsAuthenticatedAsync())
+            {
+                if (string.IsNullOrEmpty(masterKeyHash))
+                {
+                    await _cryptoService.SetUserKeyAsync(new UserKey(decryptedKey));
+                }
+                else
+                {
+                    var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(new MasterKey(decryptedKey));
+                    await _cryptoService.SetUserKeyAsync(userKey);
+                }
+                await _deviceTrustCryptoService.TrustDeviceIfNeededAsync();
+                return null;
+            }
+
+            if (string.IsNullOrEmpty(masterKeyHash) && decryptionKey != null)
+            {
+                await _cryptoService.SetUserKeyAsync(new UserKey(decryptedKey));
+                return null;
+            }
+
+            var decKeyHash = await _cryptoService.RsaDecryptAsync(masterKeyHash, decryptionKey);
+            return await LogInHelperAsync(email, accessCode, Encoding.UTF8.GetString(decKeyHash), null, null, null, new MasterKey(decryptedKey), null, null,
                 null, null, authRequestId: authRequestId);
         }
 
@@ -216,7 +242,7 @@ namespace Bit.Core.Services
             {
                 CaptchaToken = captchaToken;
             }
-            var result = await LogInHelperAsync(Email, MasterPasswordHash, LocalMasterPasswordHash, Code, CodeVerifier, SsoRedirectUrl, _key,
+            var result = await LogInHelperAsync(Email, MasterPasswordHash, LocalMasterPasswordHash, Code, CodeVerifier, SsoRedirectUrl, _masterKey,
                 twoFactorProvider, twoFactorToken, remember, CaptchaToken, authRequestId: AuthRequestId);
 
             // If we successfully authenticated and we have a saved _2faForcePasswordResetReason reason from LogInAsync()
@@ -337,7 +363,7 @@ namespace Bit.Core.Services
 
         // Helpers
 
-        private async Task<SymmetricCryptoKey> MakePreloginKeyAsync(string masterPassword, string email)
+        private async Task<MasterKey> MakePreloginKeyAsync(string masterPassword, string email)
         {
             email = email.Trim().ToLower();
             KdfConfig kdfConfig = KdfConfig.Default;
@@ -356,11 +382,11 @@ namespace Bit.Core.Services
                     throw;
                 }
             }
-            return await _cryptoService.MakeKeyAsync(masterPassword, email, kdfConfig);
+            return await _cryptoService.MakeMasterKeyAsync(masterPassword, email, kdfConfig);
         }
 
         private async Task<AuthResult> LogInHelperAsync(string email, string hashedPassword, string localHashedPassword,
-            string code, string codeVerifier, string redirectUrl, SymmetricCryptoKey key,
+            string code, string codeVerifier, string redirectUrl, MasterKey masterKey,
             TwoFactorProviderType? twoFactorProvider = null, string twoFactorToken = null, bool? remember = null,
             string captchaToken = null, string orgId = null, string authRequestId = null)
         {
@@ -426,7 +452,7 @@ namespace Bit.Core.Services
                 Code = code;
                 CodeVerifier = codeVerifier;
                 SsoRedirectUrl = redirectUrl;
-                _key = _setCryptoKeys ? key : null;
+                _masterKey = _setCryptoKeys ? masterKey : null;
                 TwoFactorProvidersData = response.TwoFactorResponse.TwoFactorProviders2;
                 result.TwoFactorProviders = response.TwoFactorResponse.TwoFactorProviders2;
                 CaptchaToken = response.TwoFactorResponse.CaptchaToken;
@@ -459,6 +485,7 @@ namespace Bit.Core.Services
                         ForcePasswordResetReason = result.ForcePasswordReset
                             ? ForcePasswordResetReason.AdminForcePasswordReset
                             : (ForcePasswordResetReason?)null,
+                        UserDecryptionOptions = tokenResponse.UserDecryptionOptions,
                     },
                     new Account.AccountTokens()
                     {
@@ -470,24 +497,46 @@ namespace Bit.Core.Services
             _messagingService.Send("accountAdded");
             if (_setCryptoKeys)
             {
-                if (key != null)
-                {
-                    await _cryptoService.SetKeyAsync(key);
-                }
-
                 if (localHashedPassword != null)
                 {
-                    await _cryptoService.SetKeyHashAsync(localHashedPassword);
+                    await _cryptoService.SetPasswordHashAsync(localHashedPassword);
+                    await _cryptoService.SetMasterKeyAsync(masterKey);
+                    var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                    await _cryptoService.SetUserKeyAsync(userKey);
                 }
 
                 if (code == null || tokenResponse.Key != null)
                 {
-                    if (tokenResponse.KeyConnectorUrl != null)
+                    var decryptOptions = await _stateService.GetAccountDecryptionOptions();
+                    await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(tokenResponse.Key);
+
+                    if (decryptOptions?.TrustedDeviceOption != null)
                     {
-                        await _keyConnectorService.GetAndSetKey(tokenResponse.KeyConnectorUrl);
+                        var key = await _deviceTrustCryptoService.DecryptUserKeyWithDeviceKeyAsync(decryptOptions.TrustedDeviceOption.EncryptedPrivateKey, decryptOptions.TrustedDeviceOption.EncryptedUserKey);
+                        if (key != null)
+                        {
+                            await _cryptoService.SetUserKeyAsync(key);
+                        }
+                    }
+                    else if (!string.IsNullOrEmpty(tokenResponse.KeyConnectorUrl) || !string.IsNullOrEmpty(decryptOptions?.KeyConnectorOption?.KeyConnectorUrl))
+                    {
+
+                        await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(tokenResponse.Key);
+                        if (masterKey != null)
+                        {
+                            await _cryptoService.SetMasterKeyAsync(masterKey);
+                            var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                            await _cryptoService.SetUserKeyAsync(userKey);
+                        }
                     }
 
-                    await _cryptoService.SetEncKeyAsync(tokenResponse.Key);
+                    // Login with Device
+                    if (masterKey != null && !string.IsNullOrEmpty(authRequestId))
+                    {
+                        await _cryptoService.SetMasterKeyAsync(masterKey);
+                        var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                        await _cryptoService.SetUserKeyAsync(userKey);
+                    }
 
                     // User doesn't have a key pair yet (old account), let's generate one for them.
                     if (tokenResponse.PrivateKey == null)
@@ -505,19 +554,22 @@ namespace Bit.Core.Services
                         catch { }
                     }
 
-                    await _cryptoService.SetEncPrivateKeyAsync(tokenResponse.PrivateKey);
+                    await _cryptoService.SetPrivateKeyAsync(tokenResponse.PrivateKey);
                 }
                 else if (tokenResponse.KeyConnectorUrl != null)
                 {
                     // SSO Key Connector Onboarding
                     var password = await _cryptoFunctionService.RandomBytesAsync(64);
-                    var k = await _cryptoService.MakeKeyAsync(Convert.ToBase64String(password), _tokenService.GetEmail(), tokenResponse.KdfConfig);
+                    var newMasterKey = await _cryptoService.MakeMasterKeyAsync(Convert.ToBase64String(password), _tokenService.GetEmail(), tokenResponse.KdfConfig);
-                    var keyConnectorRequest = new KeyConnectorUserKeyRequest(k.EncKeyB64);
+                    var keyConnectorRequest = new KeyConnectorUserKeyRequest(newMasterKey.EncKeyB64);
-                    await _cryptoService.SetKeyAsync(k);
+                    await _cryptoService.SetMasterKeyAsync(newMasterKey);
 
-                    var encKey = await _cryptoService.MakeEncKeyAsync(k);
+                    var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(
-                    await _cryptoService.SetEncKeyAsync(encKey.Item2.EncryptedString);
+                        newMasterKey,
-                    var keyPair = await _cryptoService.MakeKeyPairAsync();
+                        await _cryptoService.MakeUserKeyAsync());
+
+                    await _cryptoService.SetUserKeyAsync(newUserKey);
+                    var (newPublicKey, newProtectedPrivateKey) = await _cryptoService.MakeKeyPairAsync();
 
                     try
                     {
@@ -530,15 +582,14 @@ namespace Bit.Core.Services
 
                     var keys = new KeysRequest
                     {
-                        PublicKey = keyPair.Item1,
+                        PublicKey = newPublicKey,
-                        EncryptedPrivateKey = keyPair.Item2.EncryptedString
+                        EncryptedPrivateKey = newProtectedPrivateKey.EncryptedString
                     };
                     var setPasswordRequest = new SetKeyConnectorKeyRequest(
-                        encKey.Item2.EncryptedString, keys, tokenResponse.KdfConfig, orgId
+                        newProtectedPrivateKey.EncryptedString, keys, tokenResponse.KdfConfig, orgId
                     );
                     await _apiService.PostSetKeyConnectorKey(setPasswordRequest);
                 }
-
             }
 
             _authedUserId = _tokenService.GetUserId();
@@ -549,7 +600,7 @@ namespace Bit.Core.Services
 
         private void ClearState()
         {
-            _key = null;
+            _masterKey = null;
             Email = null;
             CaptchaToken = null;
             MasterPasswordHash = null;
@@ -575,14 +626,14 @@ namespace Bit.Core.Services
             var activeRequests = requests.Where(r => !r.IsAnswered && !r.IsExpired).OrderByDescending(r => r.CreationDate).ToList();
             return await PopulateFingerprintPhrasesAsync(activeRequests);
         }
-
         public async Task<PasswordlessLoginResponse> GetPasswordlessLoginRequestByIdAsync(string id)
         {
             var response = await _apiService.GetAuthRequestAsync(id);
             return await PopulateFingerprintPhraseAsync(response, await _stateService.GetEmailAsync());
         }
 
-        public async Task<PasswordlessLoginResponse> GetPasswordlessLoginResponseAsync(string id, string accessCode)
+        /// <inheritdoc />
+        public async Task<PasswordlessLoginResponse> GetPasswordlessLoginResquestAsync(string id, string accessCode)
         {
             return await _apiService.GetAuthResponseAsync(id, accessCode);
         }
@@ -590,15 +641,20 @@ namespace Bit.Core.Services
         public async Task<PasswordlessLoginResponse> PasswordlessLoginAsync(string id, string pubKey, bool requestApproved)
         {
             var publicKey = CoreHelpers.Base64UrlDecode(pubKey);
-            var masterKey = await _cryptoService.GetKeyAsync();
+            var masterKey = await _cryptoService.GetMasterKeyAsync();
             var encryptedKey = await _cryptoService.RsaEncryptAsync(masterKey.EncKey, publicKey);
-            var encryptedMasterPassword = await _cryptoService.RsaEncryptAsync(Encoding.UTF8.GetBytes(await _stateService.GetKeyHashAsync()), publicKey);
+            var keyHash = await _stateService.GetKeyHashAsync();
+            EncString encryptedMasterPassword = null;
+            if (!string.IsNullOrEmpty(keyHash))
+            {
+                encryptedMasterPassword = await _cryptoService.RsaEncryptAsync(Encoding.UTF8.GetBytes(keyHash), publicKey);
+            }
             var deviceId = await _appIdService.GetAppIdAsync();
-            var response = await _apiService.PutAuthRequestAsync(id, encryptedKey.EncryptedString, encryptedMasterPassword.EncryptedString, deviceId, requestApproved);
+            var response = await _apiService.PutAuthRequestAsync(id, encryptedKey.EncryptedString, encryptedMasterPassword?.EncryptedString, deviceId, requestApproved);
             return await PopulateFingerprintPhraseAsync(response, await _stateService.GetEmailAsync());
         }
 
-        public async Task<PasswordlessLoginResponse> PasswordlessCreateLoginRequestAsync(string email)
+        public async Task<PasswordlessLoginResponse> PasswordlessCreateLoginRequestAsync(string email, AuthRequestType authRequestType)
         {
             var deviceId = await _appIdService.GetAppIdAsync();
             var keyPair = await _cryptoFunctionService.RsaGenerateKeyPairAsync(2048);
@@ -606,8 +662,8 @@ namespace Bit.Core.Services
             var fingerprintPhrase = string.Join("-", generatedFingerprintPhrase);
             var publicB64 = Convert.ToBase64String(keyPair.Item1);
             var accessCode = await _passwordGenerationService.GeneratePasswordAsync(PasswordGenerationOptions.CreateDefault.WithLength(25));
-            var passwordlessCreateLoginRequest = new PasswordlessCreateLoginRequest(email, publicB64, deviceId, accessCode, AuthRequestType.AuthenticateAndUnlock, fingerprintPhrase);
+            var passwordlessCreateLoginRequest = new PasswordlessCreateLoginRequest(email, publicB64, deviceId, accessCode, authRequestType, fingerprintPhrase);
-            var response = await _apiService.PostCreateRequestAsync(passwordlessCreateLoginRequest);
+            var response = await _apiService.PostCreateRequestAsync(passwordlessCreateLoginRequest, authRequestType);
 
             if (response != null)
             {

src/Core/Services/CipherService.cs

@@ -249,7 +249,7 @@ namespace Bit.Core.Services
             {
                 try
                 {
-                    var hashKey = await _cryptoService.HasKeyAsync();
+                    var hashKey = await _cryptoService.HasUserKeyAsync();
                     if (!hashKey)
                     {
                         throw new Exception("No key.");
@@ -557,9 +557,20 @@ namespace Bit.Core.Services
 
         public async Task<Cipher> SaveAttachmentRawWithServerAsync(Cipher cipher, string filename, byte[] data)
         {
+            SymmetricCryptoKey attachmentKey;
+            EncString protectedAttachmentKey;
             var orgKey = await _cryptoService.GetOrgKeyAsync(cipher.OrganizationId);
+            if (orgKey != null)
+            {
+                (attachmentKey, protectedAttachmentKey) = await _cryptoService.MakeDataEncKeyAsync(orgKey);
+            }
+            else
+            {
+                var userKey = await _cryptoService.GetUserKeyWithLegacySupportAsync();
+                (attachmentKey, protectedAttachmentKey) = await _cryptoService.MakeDataEncKeyAsync(userKey);
+            }
+
             var encFileName = await _cryptoService.EncryptAsync(filename, orgKey);
-            var (attachmentKey, orgEncAttachmentKey) = await _cryptoService.MakeEncKeyAsync(orgKey);
             var encFileData = await _cryptoService.EncryptToBytesAsync(data, attachmentKey);
 
             CipherResponse response;
@@ -567,7 +578,7 @@ namespace Bit.Core.Services
             {
                 var request = new AttachmentRequest
                 {
-                    Key = orgEncAttachmentKey.EncryptedString,
+                    Key = protectedAttachmentKey.EncryptedString,
                     FileName = encFileName.EncryptedString,
                     FileSize = encFileData.Buffer.Length,
                 };
@@ -578,7 +589,7 @@ namespace Bit.Core.Services
             }
             catch (ApiException e) when (e.Error.StatusCode == System.Net.HttpStatusCode.NotFound || e.Error.StatusCode == System.Net.HttpStatusCode.MethodNotAllowed)
             {
-                response = await LegacyServerAttachmentFileUploadAsync(cipher.Id, encFileName, encFileData, orgEncAttachmentKey);
+                response = await LegacyServerAttachmentFileUploadAsync(cipher.Id, encFileName, encFileData, protectedAttachmentKey);
             }
 
             var userId = await _stateService.GetActiveUserIdAsync();
@@ -807,14 +818,27 @@ namespace Bit.Core.Services
 
             var bytes = await attachmentResponse.Content.ReadAsByteArrayAsync();
             var decBytes = await _cryptoService.DecryptFromBytesAsync(bytes, null);
-            var key = await _cryptoService.GetOrgKeyAsync(organizationId);
+
-            var encFileName = await _cryptoService.EncryptAsync(attachmentView.FileName, key);
+            SymmetricCryptoKey attachmentKey;
-            var dataEncKey = await _cryptoService.MakeEncKeyAsync(key);
+            EncString protectedAttachmentKey;
-            var encData = await _cryptoService.EncryptToBytesAsync(decBytes, dataEncKey.Item1);
+            var orgKey = await _cryptoService.GetOrgKeyAsync(organizationId);
+            if (orgKey != null)
+            {
+                (attachmentKey, protectedAttachmentKey) = await _cryptoService.MakeDataEncKeyAsync(orgKey);
+            }
+            else
+            {
+                var userKey = await _cryptoService.GetUserKeyWithLegacySupportAsync();
+                (attachmentKey, protectedAttachmentKey) = await _cryptoService.MakeDataEncKeyAsync(userKey);
+            }
+
+            var encFileName = await _cryptoService.EncryptAsync(attachmentView.FileName, orgKey);
+            var encFileData = await _cryptoService.EncryptToBytesAsync(decBytes, attachmentKey);
+
             var boundary = string.Concat("--BWMobileFormBoundary", DateTime.UtcNow.Ticks);
             var fd = new MultipartFormDataContent(boundary);
-            fd.Add(new StringContent(dataEncKey.Item2.EncryptedString), "key");
+            fd.Add(new StringContent(protectedAttachmentKey.EncryptedString), "key");
-            fd.Add(new StreamContent(new MemoryStream(encData.Buffer)), "data", encFileName.EncryptedString);
+            fd.Add(new StreamContent(new MemoryStream(encFileData.Buffer)), "data", encFileName.EncryptedString);
             await _apiService.PostShareCipherAttachmentAsync(cipherId, attachmentView.Id, fd, organizationId);
         }
 

src/Core/Services/CollectionService.cs

@@ -101,7 +101,7 @@ namespace Bit.Core.Services
             {
                 return _decryptedCollectionCache;
             }
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
                 throw new Exception("No key.");

src/Core/Services/DeviceTrustCryptoService.cs

@@ -0,0 +1,129 @@
+
+using System;
+using System.Threading.Tasks;
+using Bit.Core.Abstractions;
+using Bit.Core.Models.Domain;
+using Bit.Core.Models.Request;
+
+namespace Bit.Core.Services
+{
+    public class DeviceTrustCryptoService : IDeviceTrustCryptoService
+    {
+        private readonly IApiService _apiService;
+        private readonly IAppIdService _appIdService;
+        private readonly ICryptoFunctionService _cryptoFunctionService;
+        private readonly ICryptoService _cryptoService;
+        private readonly IStateService _stateService;
+
+        private const int DEVICE_KEY_SIZE = 64;
+
+        public DeviceTrustCryptoService(
+            IApiService apiService,
+            IAppIdService appIdService,
+            ICryptoFunctionService cryptoFunctionService,
+            ICryptoService cryptoService,
+            IStateService stateService)
+        {
+            _apiService = apiService;
+            _appIdService = appIdService;
+            _cryptoFunctionService = cryptoFunctionService;
+            _cryptoService = cryptoService;
+            _stateService = stateService;
+        }
+
+        public async Task<SymmetricCryptoKey> GetDeviceKeyAsync()
+        {
+            return await _stateService.GetDeviceKeyAsync();
+        }
+
+        private async Task SetDeviceKeyAsync(SymmetricCryptoKey deviceKey)
+        {
+            await _stateService.SetDeviceKeyAsync(deviceKey);
+        }
+
+        public async Task<DeviceResponse> TrustDeviceAsync()
+        {
+            // Attempt to get user key
+            var userKey = await _cryptoService.GetUserKeyAsync();
+            if (userKey == null)
+            {
+                return null;
+            }
+            // Generate deviceKey
+            var deviceKey = await MakeDeviceKeyAsync();
+
+            // Generate asymmetric RSA key pair: devicePrivateKey, devicePublicKey
+            var (devicePublicKey, devicePrivateKey) = await _cryptoFunctionService.RsaGenerateKeyPairAsync(2048);
+
+            // Send encrypted keys to server
+            var deviceIdentifier = await _appIdService.GetAppIdAsync();
+            var deviceRequest = new TrustedDeviceKeysRequest
+            {
+                EncryptedUserKey = (await _cryptoService.RsaEncryptAsync(userKey.Key, devicePublicKey)).EncryptedString,
+                EncryptedPublicKey = (await _cryptoService.EncryptAsync(devicePublicKey, userKey)).EncryptedString,
+                EncryptedPrivateKey = (await _cryptoService.EncryptAsync(devicePrivateKey, deviceKey)).EncryptedString,
+            };
+
+            var deviceResponse = await _apiService.UpdateTrustedDeviceKeysAsync(deviceIdentifier, deviceRequest);
+
+            // Store device key if successful
+            await SetDeviceKeyAsync(deviceKey);
+            return deviceResponse;
+        }
+
+        private async Task<SymmetricCryptoKey> MakeDeviceKeyAsync()
+        {
+            // Create 512-bit device key
+            var randomBytes = await _cryptoFunctionService.RandomBytesAsync(DEVICE_KEY_SIZE);
+            return new SymmetricCryptoKey(randomBytes);
+        }
+
+        public async Task<bool> GetShouldTrustDeviceAsync()
+        {
+            return await _stateService.GetShouldTrustDeviceAsync();
+        }
+
+        public async Task SetShouldTrustDeviceAsync(bool value)
+        {
+            await _stateService.SetShouldTrustDeviceAsync(value);
+        }
+
+        public async Task<DeviceResponse> TrustDeviceIfNeededAsync()
+        {
+            if (!await GetShouldTrustDeviceAsync())
+            {
+                return null;
+            }
+
+            var response = await TrustDeviceAsync();
+            await SetShouldTrustDeviceAsync(false);
+            return response;
+        }
+
+        public async Task<bool> IsDeviceTrustedAsync()
+        {
+            var existingDeviceKey = await GetDeviceKeyAsync();
+            return existingDeviceKey != null;
+        }
+
+        public async Task<UserKey> DecryptUserKeyWithDeviceKeyAsync(string encryptedDevicePrivateKey, string encryptedUserKey)
+        {
+            var existingDeviceKey = await GetDeviceKeyAsync();
+            if (existingDeviceKey == null)
+            {
+                // User doesn't have a device key anymore so device is untrusted
+                return null;
+            }
+
+            // Attempt to decrypt encryptedDevicePrivateKey with device key
+            var devicePrivateKeyBytes = await _cryptoService.DecryptToBytesAsync(
+              new EncString(encryptedDevicePrivateKey),
+              existingDeviceKey
+            );
+
+            // Attempt to decrypt encryptedUserDataKey with devicePrivateKey
+            var userKeyBytes = await _cryptoService.RsaDecryptAsync(encryptedUserKey, devicePrivateKeyBytes);
+            return new UserKey(userKeyBytes);
+        }
+    }
+}

src/Core/Services/FolderService.cs

@@ -77,7 +77,7 @@ namespace Bit.Core.Services
             {
                 return _decryptedFolderCache;
             }
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
                 throw new Exception("No key.");

src/Core/Services/KeyConnectorService.cs

@@ -28,10 +28,10 @@ namespace Bit.Core.Services
         {
             try
             {
-                var userKeyResponse = await _apiService.GetUserKeyFromKeyConnector(url);
+                var masterKeyResponse = await _apiService.GetMasterKeyFromKeyConnector(url);
-                var keyArr = Convert.FromBase64String(userKeyResponse.Key);
+                var masterKeyArr = Convert.FromBase64String(masterKeyResponse.Key);
-                var k = new SymmetricCryptoKey(keyArr);
+                var masterKey = new MasterKey(masterKeyArr);
-                await _cryptoService.SetKeyAsync(k);
+                await _cryptoService.SetMasterKeyAsync(masterKey);
             }
             catch (Exception e)
             {
@@ -60,11 +60,11 @@ namespace Bit.Core.Services
         public async Task MigrateUser()
         {
             var organization = await GetManagingOrganization();
-            var key = await _cryptoService.GetKeyAsync();
+            var masterKey = await _cryptoService.GetMasterKeyAsync();
 
             try
             {
-                var keyConnectorRequest = new KeyConnectorUserKeyRequest(key.EncKeyB64);
+                var keyConnectorRequest = new KeyConnectorUserKeyRequest(masterKey.EncKeyB64);
                 await _apiService.PostUserKeyToKeyConnector(organization.KeyConnectorUrl, keyConnectorRequest);
             }
             catch (Exception e)

src/Core/Services/PasswordGenerationService.cs

@@ -247,7 +247,7 @@ namespace Bit.Core.Services
 
         public async Task<List<GeneratedPasswordHistory>> GetHistoryAsync()
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
                 return new List<GeneratedPasswordHistory>();
@@ -262,7 +262,7 @@ namespace Bit.Core.Services
 
         public async Task AddHistoryAsync(string password, CancellationToken token = default(CancellationToken))
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
                 return;

src/Core/Services/SendService.cs

@@ -143,7 +143,7 @@ namespace Bit.Core.Services
                 return _decryptedSendsCache;
             }
 
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
                 throw new Exception("No Key.");

src/Core/Services/StateService.cs

@@ -302,6 +302,52 @@ namespace Bit.Core.Services
                 true, reconciledOptions);
         }
 
+        public async Task<UserKey> GetUserKeyAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.UserKey;
+        }
+
+        public async Task SetUserKeyAsync(UserKey value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            var account = await GetAccountAsync(reconciledOptions);
+            account.VolatileData.UserKey = value;
+            await SaveAccountAsync(account, reconciledOptions);
+        }
+
+        public async Task<MasterKey> GetMasterKeyAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.MasterKey;
+        }
+
+        public async Task SetMasterKeyAsync(MasterKey value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            var account = await GetAccountAsync(reconciledOptions);
+            account.VolatileData.MasterKey = value;
+            await SaveAccountAsync(account, reconciledOptions);
+        }
+
+        public async Task<string> GetUserKeyMasterKeyAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            return await _storageMediatorService.GetAsync<string>(Constants.UserKeyKey(reconciledOptions.UserId), false);
+        }
+
+        public async Task SetUserKeyMasterKeyAsync(string value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            await _storageMediatorService.SaveAsync(Constants.UserKeyKey(reconciledOptions.UserId), value, false);
+        }
+
         public async Task<bool> CanAccessPremiumAsync(string userId = null)
         {
             if (userId == null)
@@ -353,6 +399,34 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.ProtectedPinKey(reconciledOptions.UserId), value, reconciledOptions);
         }
 
+        public async Task<EncString> GetUserKeyPinAsync(string userId = null)
+        {
+            var key = await _storageMediatorService.GetAsync<string>(Constants.UserKeyPinKey(userId), false);
+            return key != null ? new EncString(key) : null;
+        }
+
+        public async Task SetUserKeyPinAsync(EncString value, string userId = null)
+        {
+            await _storageMediatorService.SaveAsync(Constants.UserKeyPinKey(userId), value?.EncryptedString, false);
+        }
+
+        public async Task<EncString> GetUserKeyPinEphemeralAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.UserKeyPinEphemeral;
+        }
+
+        public async Task SetUserKeyPinEphemeralAsync(EncString value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            var account = await GetAccountAsync(reconciledOptions);
+            account.VolatileData.UserKeyPinEphemeral = value;
+            await SaveAccountAsync(account, reconciledOptions);
+        }
+
+        [Obsolete("Use GetUserKeyPinAsync instead, left for migration purposes")]
         public async Task<string> GetPinProtectedAsync(string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -360,6 +434,7 @@ namespace Bit.Core.Services
             return await GetValueAsync<string>(Constants.PinProtectedKey(reconciledOptions.UserId), reconciledOptions);
         }
 
+        [Obsolete("Use SetUserKeyPinAsync instead")]
         public async Task SetPinProtectedAsync(string value, string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -367,6 +442,7 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.PinProtectedKey(reconciledOptions.UserId), value, reconciledOptions);
         }
 
+        [Obsolete("Use GetUserKeyPinEphemeralAsync instead, left for migration purposes")]
         public async Task<EncString> GetPinProtectedKeyAsync(string userId = null)
         {
             return (await GetAccountAsync(
@@ -374,6 +450,7 @@ namespace Bit.Core.Services
             ))?.VolatileData?.PinProtectedKey;
         }
 
+        [Obsolete("Use SetUserKeyPinEphemeralAsync instead")]
         public async Task SetPinProtectedKeyAsync(EncString value, string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -395,35 +472,6 @@ namespace Bit.Core.Services
             await SaveAccountAsync(account, reconciledOptions);
         }
 
-        public async Task<string> GetKeyEncryptedAsync(string userId = null)
-        {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultSecureStorageOptionsAsync());
-            return await GetValueAsync<string>(Constants.KeyKey(reconciledOptions.UserId), reconciledOptions);
-        }
-
-        public async Task SetKeyEncryptedAsync(string value, string userId)
-        {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultSecureStorageOptionsAsync());
-            await SetValueAsync(Constants.KeyKey(reconciledOptions.UserId), value, reconciledOptions);
-        }
-
-        public async Task<SymmetricCryptoKey> GetKeyDecryptedAsync(string userId = null)
-        {
-            return (await GetAccountAsync(
-                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
-            ))?.VolatileData?.Key;
-        }
-
-        public async Task SetKeyDecryptedAsync(SymmetricCryptoKey value, string userId = null)
-        {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultInMemoryOptionsAsync());
-            var account = await GetAccountAsync(reconciledOptions);
-            account.VolatileData.Key = value;
-            await SaveAccountAsync(account, reconciledOptions);
-        }
 
         public async Task<string> GetKeyHashAsync(string userId = null)
         {
@@ -439,19 +487,6 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.KeyHashKey(reconciledOptions.UserId), value, reconciledOptions);
         }
 
-        public async Task<string> GetEncKeyEncryptedAsync(string userId = null)
-        {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultStorageOptionsAsync());
-            return await GetValueAsync<string>(Constants.EncKeyKey(reconciledOptions.UserId), reconciledOptions);
-        }
-
-        public async Task SetEncKeyEncryptedAsync(string value, string userId)
-        {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultStorageOptionsAsync());
-            await SetValueAsync(Constants.EncKeyKey(reconciledOptions.UserId), value, reconciledOptions);
-        }
 
         public async Task<Dictionary<string, string>> GetOrgKeysEncryptedAsync(string userId = null)
         {
@@ -482,6 +517,25 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.EncPrivateKeyKey(reconciledOptions.UserId), value, reconciledOptions);
         }
 
+        public async Task<SymmetricCryptoKey> GetDeviceKeyAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            var deviceKeyB64 = await _storageMediatorService.GetAsync<string>(Constants.DeviceKeyKey(reconciledOptions.UserId), true);
+            if (string.IsNullOrEmpty(deviceKeyB64))
+            {
+                return null;
+            }
+            return new SymmetricCryptoKey(Convert.FromBase64String(deviceKeyB64));
+        }
+
+        public async Task SetDeviceKeyAsync(SymmetricCryptoKey value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            await _storageMediatorService.SaveAsync(Constants.DeviceKeyKey(reconciledOptions.UserId), value.KeyB64, true);
+        }
+
         public async Task<List<string>> GetAutofillBlacklistedUrisAsync(string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -1280,6 +1334,37 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.PreLoginEmailKey, value, options);
         }
 
+        public async Task<AccountDecryptionOptions> GetAccountDecryptionOptions(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultStorageOptionsAsync())
+            ))?.Profile?.UserDecryptionOptions;
+        }
+
+        public async Task<bool> GetShouldTrustDeviceAsync()
+        {
+            return await _storageMediatorService.GetAsync<bool>(Constants.ShouldTrustDevice);
+        }
+
+        public async Task SetShouldTrustDeviceAsync(bool value)
+        {
+            await _storageMediatorService.SaveAsync(Constants.ShouldTrustDevice, value);
+        }
+
+        public async Task<PendingAdminAuthRequest> GetPendingAdminAuthRequestAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            return await _storageMediatorService.GetAsync<PendingAdminAuthRequest>(Constants.PendingAdminAuthRequest(reconciledOptions.UserId), true);
+        }
+
+        public async Task SetPendingAdminAuthRequestAsync(PendingAdminAuthRequest value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            await _storageMediatorService.SaveAsync(Constants.PendingAdminAuthRequest(reconciledOptions.UserId), value, true);
+        }
+
         public ConfigResponse GetConfigs()
         {
             return _storageMediatorService.Get<ConfigResponse>(Constants.ConfigsKey);
@@ -1656,5 +1741,55 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.LastUserShouldConnectToWatchKey,
                 shouldConnect ?? await GetShouldConnectToWatchAsync(), await GetDefaultStorageOptionsAsync());
         }
+
+        [Obsolete]
+        public async Task<string> GetEncKeyEncryptedAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            return await GetValueAsync<string>(Constants.EncKeyKey(reconciledOptions.UserId), reconciledOptions);
+        }
+
+        [Obsolete]
+        public async Task SetEncKeyEncryptedAsync(string value, string userId)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            await SetValueAsync(Constants.EncKeyKey(reconciledOptions.UserId), value, reconciledOptions);
+        }
+
+        [Obsolete]
+        public async Task<string> GetKeyEncryptedAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultSecureStorageOptionsAsync());
+            return await GetValueAsync<string>(Constants.KeyKey(reconciledOptions.UserId), reconciledOptions);
+        }
+
+        [Obsolete]
+        public async Task SetKeyEncryptedAsync(string value, string userId)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultSecureStorageOptionsAsync());
+            await SetValueAsync(Constants.KeyKey(reconciledOptions.UserId), value, reconciledOptions);
+        }
+
+        [Obsolete]
+        public async Task<SymmetricCryptoKey> GetKeyDecryptedAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.Key;
+        }
+
+        [Obsolete]
+        public async Task SetKeyDecryptedAsync(SymmetricCryptoKey value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            var account = await GetAccountAsync(reconciledOptions);
+            account.VolatileData.Key = value;
+            await SaveAccountAsync(account, reconciledOptions);
+        }
     }
 }

src/Core/Services/SyncService.cs

@@ -327,8 +327,8 @@ namespace Bit.Core.Services
                 }
                 return;
             }
-            await _cryptoService.SetEncKeyAsync(response.Key);
+            await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(response.Key);
-            await _cryptoService.SetEncPrivateKeyAsync(response.PrivateKey);
+            await _cryptoService.SetPrivateKeyAsync(response.PrivateKey);
             await _cryptoService.SetOrgKeysAsync(response.Organizations);
             await _stateService.SetSecurityStampAsync(response.SecurityStamp);
             var organizations = response.Organizations.ToDictionary(o => o.Id, o => new OrganizationData(o));

src/Core/Services/UserVerificationService.cs

@@ -44,7 +44,7 @@ namespace Bit.Core.Services
             }
             else
             {
-                var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(secret, null);
+                var passwordValid = await _cryptoService.CompareAndUpdatePasswordHashAsync(secret, null);
                 if (!passwordValid)
                 {
                     await InvalidSecretErrorAsync(verificationType);

src/Core/Services/VaultTimeoutService.cs

@@ -7,6 +7,13 @@ using Bit.Core.Models.Domain;
 
 namespace Bit.Core.Services
 {
+    public enum PinLockEnum
+    {
+        Disabled,
+        Persistent,
+        Transient
+    }
+
     public class VaultTimeoutService : IVaultTimeoutService
     {
         private readonly ICryptoService _cryptoService;
@@ -54,7 +61,7 @@ namespace Bit.Core.Services
 
         public async Task<bool> IsLockedAsync(string userId = null)
         {
-            var hasKey = await _cryptoService.HasKeyAsync(userId);
+            var hasKey = await _cryptoService.HasUserKeyAsync(userId);
             if (hasKey)
             {
                 var biometricSet = await IsBiometricLockSetAsync(userId);
@@ -165,11 +172,13 @@ namespace Bit.Core.Services
 
             if (await _keyConnectorService.GetUsesKeyConnector())
             {
-                var (isPinProtected, isPinProtectedWithKey) = await IsPinLockSetAsync(userId);
+                var pinStatus = await IsPinLockSetAsync(userId);
-                var pinLock = (isPinProtected && await _stateService.GetPinProtectedKeyAsync(userId) != null) ||
+                var ephemeralPinSet = await _stateService.GetUserKeyPinEphemeralAsync()
-                              isPinProtectedWithKey;
+                    ?? await _stateService.GetPinProtectedKeyAsync();
+                var pinEnabled = (pinStatus == PinLockEnum.Transient && ephemeralPinSet != null) ||
+                          pinStatus == PinLockEnum.Persistent;
 
-                if (!pinLock && !await IsBiometricLockSetAsync())
+                if (!pinEnabled && !await IsBiometricLockSetAsync())
                 {
                     await LogOutAsync(userInitiated, userId);
                     return;
@@ -187,10 +196,10 @@ namespace Bit.Core.Services
                 }
             }
             await Task.WhenAll(
-                _cryptoService.ClearKeyAsync(userId),
+                _cryptoService.ClearUserKeyAsync(userId),
+                _cryptoService.ClearMasterKeyAsync(userId),
                 _cryptoService.ClearOrgKeysAsync(true, userId),
-                _cryptoService.ClearKeyPairAsync(true, userId),
+                _cryptoService.ClearKeyPairAsync(true, userId));
-                _cryptoService.ClearEncKeyAsync(true, userId));
 
             if (isActiveAccount)
             {
@@ -214,15 +223,30 @@ namespace Bit.Core.Services
         {
             await _stateService.SetVaultTimeoutAsync(timeout);
             await _stateService.SetVaultTimeoutActionAsync(action);
-            await _cryptoService.ToggleKeyAsync();
+            await _cryptoService.ToggleKeysAsync();
             await _tokenService.ToggleTokensAsync();
         }
 
-        public async Task<Tuple<bool, bool>> IsPinLockSetAsync(string userId = null)
+        public async Task<PinLockEnum> IsPinLockSetAsync(string userId = null)
         {
-            var protectedPin = await _stateService.GetProtectedPinAsync(userId);
+            // we can't depend on only the protected pin being set because old
-            var pinProtectedKey = await _stateService.GetPinProtectedAsync(userId);
+            // versions only used it for MP on Restart
-            return new Tuple<bool, bool>(protectedPin != null, pinProtectedKey != null);
+            var pinIsEnabled = await _stateService.GetProtectedPinAsync(userId);
+            var userKeyPin = await _stateService.GetUserKeyPinAsync(userId);
+            var oldUserKeyPin = await _stateService.GetPinProtectedAsync(userId);
+
+            if (userKeyPin != null || oldUserKeyPin != null)
+            {
+                return PinLockEnum.Persistent;
+            }
+            else if (pinIsEnabled != null && userKeyPin == null && oldUserKeyPin == null)
+            {
+                return PinLockEnum.Transient;
+            }
+            else
+            {
+                return PinLockEnum.Disabled;
+            }
         }
 
         public async Task<bool> IsBiometricLockSetAsync(string userId = null)
@@ -233,8 +257,7 @@ namespace Bit.Core.Services
 
         public async Task ClearAsync(string userId = null)
         {
-            await _stateService.SetPinProtectedKeyAsync(null, userId);
+            await _cryptoService.ClearPinKeysAsync(userId);
-            await _stateService.SetProtectedPinAsync(null, userId);
         }
 
         public async Task<int?> GetVaultTimeout(string userId = null)

src/Core/Utilities/ServiceContainer.cs

@@ -77,9 +77,10 @@ namespace Bit.Core.Utilities
                 });
             var passwordGenerationService = new PasswordGenerationService(cryptoService, stateService, cryptoFunctionService, policyService);
             var totpService = new TotpService(cryptoFunctionService);
+            var deviceTrustCryptoService = new DeviceTrustCryptoService(apiService, appIdService, cryptoFunctionService, cryptoService, stateService);
             var authService = new AuthService(cryptoService, cryptoFunctionService, apiService, stateService,
                 tokenService, appIdService, i18nService, platformUtilsService, messagingService, vaultTimeoutService,
-                keyConnectorService, passwordGenerationService, policyService);
+                keyConnectorService, passwordGenerationService, policyService, deviceTrustCryptoService);
             var exportService = new ExportService(folderService, cipherService, cryptoService);
             var auditService = new AuditService(cryptoFunctionService, apiService);
             var environmentService = new EnvironmentService(apiService, stateService, conditionedRunner);
@@ -114,6 +115,7 @@ namespace Bit.Core.Utilities
             Register<IUserVerificationService>("userVerificationService", userVerificationService);
             Register<IUsernameGenerationService>(usernameGenerationService);
             Register<IConfigService>(configService);
+            Register<IDeviceTrustCryptoService>(deviceTrustCryptoService);
         }
 
         public static void Register<T>(string serviceName, T obj)

src/iOS.Autofill/CredentialProviderViewController.cs

@@ -498,7 +498,7 @@ namespace Bit.iOS.Autofill
                 vm.StartTwoFactorAction = () => DismissViewController(false, () => LaunchTwoFactorFlow(false));
                 vm.UpdateTempPasswordAction = () => DismissViewController(false, () => LaunchUpdateTempPasswordFlow());
                 vm.StartSsoLoginAction = () => DismissViewController(false, () => LaunchLoginSsoFlow());
-                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(email));
+                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, email));
                 vm.LogInSuccessAction = () => DismissLockAndContinue();
                 vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
             }
@@ -511,11 +511,11 @@ namespace Bit.iOS.Autofill
             LogoutIfAuthed();
         }
 
-        private void LaunchLoginWithDevice(string email = null)
+        private void LaunchLoginWithDevice(AuthRequestType authRequestType, string email = null)
         {
             var appOptions = new AppOptions { IosExtension = true };
             var app = new App.App(appOptions);
-            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, appOptions);
+            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, authRequestType, appOptions);
             ThemeManager.SetTheme(app.Resources);
             ThemeManager.ApplyResourcesTo(loginWithDevicePage);
             if (loginWithDevicePage.BindingContext is LoginPasswordlessRequestViewModel vm)
@@ -545,6 +545,7 @@ namespace Bit.iOS.Autofill
                 vm.StartTwoFactorAction = () => DismissViewController(false, () => LaunchTwoFactorFlow(true));
                 vm.StartSetPasswordAction = () => DismissViewController(false, () => LaunchSetPasswordFlow());
                 vm.UpdateTempPasswordAction = () => DismissViewController(false, () => LaunchUpdateTempPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 vm.SsoAuthSuccessAction = () => DismissLockAndContinue();
                 vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
             }
@@ -567,6 +568,7 @@ namespace Bit.iOS.Autofill
             {
                 vm.TwoFactorAuthSuccessAction = () => DismissLockAndContinue();
                 vm.StartSetPasswordAction = () => DismissViewController(false, () => LaunchSetPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 if (authingWithSso)
                 {
                     vm.CloseAction = () => DismissViewController(false, () => LaunchLoginSsoFlow());
@@ -621,6 +623,26 @@ namespace Bit.iOS.Autofill
             PresentViewController(updateTempPasswordController, true, null);
         }
 
+        private void LaunchDeviceApprovalOptionsFlow()
+        {
+            var loginApproveDevicePage = new LoginApproveDevicePage();
+            var app = new App.App(new AppOptions { IosExtension = true });
+            ThemeManager.SetTheme(app.Resources);
+            ThemeManager.ApplyResourcesTo(loginApproveDevicePage);
+            if (loginApproveDevicePage.BindingContext is LoginApproveDeviceViewModel vm)
+            {
+                vm.LogInWithMasterPasswordAction = () => DismissViewController(false, () => PerformSegue("lockPasswordSegue", this));
+                vm.RequestAdminApprovalAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AdminApproval, vm.Email));
+                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, vm.Email));
+                vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
+            }
+
+            var navigationPage = new NavigationPage(loginApproveDevicePage);
+            var loginApproveDeviceController = navigationPage.CreateViewController();
+            loginApproveDeviceController.ModalPresentationStyle = UIModalPresentationStyle.FullScreen;
+            PresentViewController(loginApproveDeviceController, true, null);
+        }
+
         public Task SetPreviousPageInfoAsync() => Task.CompletedTask;
         public Task UpdateThemeAsync() => Task.CompletedTask;
 

src/iOS.Core/Controllers/BaseLockPasswordViewController.cs

@@ -8,11 +8,13 @@ using Bit.App.Utilities;
 using Bit.Core.Abstractions;
 using Bit.Core.Enums;
 using Bit.Core.Models.Domain;
+using Bit.Core.Services;
 using Bit.Core.Utilities;
 using Bit.iOS.Core.Utilities;
 using Bit.iOS.Core.Views;
 using Foundation;
 using UIKit;
+using Xamarin.Essentials;
 using Xamarin.Forms;
 
 namespace Bit.iOS.Core.Controllers
@@ -28,10 +30,9 @@ namespace Bit.iOS.Core.Controllers
         private IBiometricService _biometricService;
         private IKeyConnectorService _keyConnectorService;
         private IAccountsManager _accountManager;
-        private bool _isPinProtected;
+        private PinLockEnum _pinStatus;
-        private bool _isPinProtectedWithKey;
+        private bool _pinEnabled;
-        private bool _pinLock;
+        private bool _biometricEnabled;
-        private bool _biometricLock;
         private bool _biometricIntegrityValid = true;
         private bool _passwordReprompt = false;
         private bool _usesKeyConnector;
@@ -103,25 +104,28 @@ namespace Bit.iOS.Core.Controllers
             if (autofillExtension && await _stateService.GetPasswordRepromptAutofillAsync())
             {
                 _passwordReprompt = true;
-                _isPinProtected = false;
+                _pinStatus = PinLockEnum.Disabled;
-                _isPinProtectedWithKey = false;
+                _pinEnabled = false;
-                _pinLock = false;
+                _biometricEnabled = false;
-                _biometricLock = false;
             }
             else
             {
-                (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
+                _pinStatus = await _vaultTimeoutService.IsPinLockSetAsync();
-                _pinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
+
-                           _isPinProtectedWithKey;
+                var ephemeralPinSet = await _stateService.GetUserKeyPinEphemeralAsync()
-                _biometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() &&
+                    ?? await _stateService.GetPinProtectedKeyAsync();
-                                 await _cryptoService.HasKeyAsync();
+                _pinEnabled = (_pinStatus == PinLockEnum.Transient && ephemeralPinSet != null) ||
+                    _pinStatus == PinLockEnum.Persistent;
+
+                _biometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync()
+                    && await _cryptoService.HasEncryptedUserKeyAsync();
                 _biometricIntegrityValid =
                     await _platformUtilsService.IsBiometricIntegrityValidAsync(BiometricIntegritySourceKey);
                 _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-                _biometricUnlockOnly = _usesKeyConnector && _biometricLock && !_pinLock;
+                _biometricUnlockOnly = _usesKeyConnector && _biometricEnabled && !_pinEnabled;
             }
 
-            if (_pinLock)
+            if (_pinEnabled)
             {
                 BaseNavItem.Title = AppResources.VerifyPIN;
             }
@@ -150,7 +154,7 @@ namespace Bit.iOS.Core.Controllers
 
             if (!_biometricUnlockOnly)
             {
-                MasterPasswordCell.Label.Text = _pinLock ? AppResources.PIN : AppResources.MasterPassword;
+                MasterPasswordCell.Label.Text = _pinEnabled ? AppResources.PIN : AppResources.MasterPassword;
                 MasterPasswordCell.TextField.SecureTextEntry = true;
                 MasterPasswordCell.TextField.ReturnKeyType = UIReturnKeyType.Go;
                 MasterPasswordCell.TextField.ShouldReturn += (UITextField tf) =>
@@ -158,7 +162,7 @@ namespace Bit.iOS.Core.Controllers
                     CheckPasswordAsync().FireAndForget();
                     return true;
                 };
-                if (_pinLock)
+                if (_pinEnabled)
                 {
                     MasterPasswordCell.TextField.KeyboardType = UIKeyboardType.NumberPad;
                 }
@@ -177,7 +181,7 @@ namespace Bit.iOS.Core.Controllers
 
             base.ViewDidLoad();
 
-            if (_biometricLock)
+            if (_biometricEnabled)
             {
                 if (!_biometricIntegrityValid)
                 {
@@ -198,13 +202,13 @@ namespace Bit.iOS.Core.Controllers
             // Users with key connector and without biometric or pin has no MP to unlock with
             if (_usesKeyConnector)
             {
-                if (!(_pinLock || _biometricLock) ||
+                if (!(_pinEnabled || _biometricEnabled) ||
-                    (_biometricLock && !_biometricIntegrityValid))
+                    (_biometricEnabled && !_biometricIntegrityValid))
                 {
                     PromptSSO();
                 }
             }
-            else if (!_biometricLock || !_biometricIntegrityValid)
+            else if (!_biometricEnabled || !_biometricIntegrityValid)
             {
                 MasterPasswordCell.TextField.BecomeFirstResponder();
             }
@@ -224,7 +228,7 @@ namespace Bit.iOS.Core.Controllers
                 {
                     var alert = Dialogs.CreateAlert(AppResources.AnErrorHasOccurred,
                         string.Format(AppResources.ValidationFieldRequired,
-                            _pinLock ? AppResources.PIN : AppResources.MasterPassword),
+                            _pinEnabled ? AppResources.PIN : AppResources.MasterPassword),
                         AppResources.Ok);
                     PresentViewController(alert, true, null);
                     return;
@@ -246,33 +250,53 @@ namespace Bit.iOS.Core.Controllers
                     return;
                 }
 
-                if (_pinLock)
+                if (_pinEnabled)
                 {
                     var failed = true;
                     try
                     {
-                        if (_isPinProtected)
+                        EncString userKeyPin = null;
+                        EncString oldPinProtected = null;
+                        if (_pinStatus == PinLockEnum.Persistent)
                         {
-                            var key = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                            userKeyPin = await _stateService.GetUserKeyPinAsync();
-                                kdfConfig,
+                            var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
-                                await _stateService.GetPinProtectedKeyAsync());
+                            oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
-                            var encKey = await _cryptoService.GetEncKeyAsync(key);
-                            var protectedPin = await _stateService.GetProtectedPinAsync();
-                            var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                            failed = decPin != inputtedValue;
-                            if (!failed)
-                            {
-                                await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                                await SetKeyAndContinueAsync(key);
                         }
+                        else if (_pinStatus == PinLockEnum.Transient)
+                        {
+                            userKeyPin = await _stateService.GetUserKeyPinEphemeralAsync();
+                            oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                        }
+
+                        UserKey userKey;
+                        if (oldPinProtected != null)
+                        {
+                            userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                                _pinStatus == PinLockEnum.Transient,
+                                inputtedValue,
+                                email,
+                                kdfConfig,
+                                oldPinProtected
+                            );
                         }
                         else
                         {
-                            var key2 = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                            userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
-                                kdfConfig);
+                                inputtedValue,
-                            failed = false;
+                                email,
+                                kdfConfig,
+                                userKeyPin
+                            );
+                        }
+
+                        var protectedPin = await _stateService.GetProtectedPinAsync();
+                        var decryptedPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), userKey);
+                        failed = decryptedPin != inputtedValue;
+                        if (!failed)
+                        {
                             await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                            await SetKeyAndContinueAsync(key2);
+                            await SetKeyAndContinueAsync(userKey);
                         }
                     }
                     catch
@@ -286,33 +310,27 @@ namespace Bit.iOS.Core.Controllers
                 }
                 else
                 {
-                    var key2 = await _cryptoService.MakeKeyAsync(inputtedValue, email, kdfConfig);
+                    var masterKey = await _cryptoService.MakeMasterKeyAsync(inputtedValue, email, kdfConfig);
 
-                    var storedKeyHash = await _cryptoService.GetKeyHashAsync();
+                    var storedPasswordHash = await _cryptoService.GetPasswordHashAsync();
-                    if (storedKeyHash == null)
+                    if (storedPasswordHash == null)
                     {
                         var oldKey = await _secureStorageService.GetAsync<string>("oldKey");
-                        if (key2.KeyB64 == oldKey)
+                        if (masterKey.KeyB64 == oldKey)
                         {
-                            var localKeyHash = await _cryptoService.HashPasswordAsync(inputtedValue, key2, HashPurpose.LocalAuthorization);
+                            var localPasswordHash = await _cryptoService.HashPasswordAsync(inputtedValue, masterKey, HashPurpose.LocalAuthorization);
                             await _secureStorageService.RemoveAsync("oldKey");
-                            await _cryptoService.SetKeyHashAsync(localKeyHash);
+                            await _cryptoService.SetPasswordHashAsync(localPasswordHash);
                         }
                     }
-                    var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(inputtedValue, key2);
+                    var passwordValid = await _cryptoService.CompareAndUpdatePasswordHashAsync(inputtedValue, masterKey);
                     if (passwordValid)
                     {
-                        if (_isPinProtected)
-                        {
-                            var protectedPin = await _stateService.GetProtectedPinAsync();
-                            var encKey = await _cryptoService.GetEncKeyAsync(key2);
-                            var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                            var pinKey = await _cryptoService.MakePinKeyAysnc(decPin, email,
-                                kdfConfig);
-                            await _stateService.SetPinProtectedKeyAsync(await _cryptoService.EncryptAsync(key2.Key, pinKey));
-                        }
                         await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                        await SetKeyAndContinueAsync(key2, true);
+
+                        var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                        await _cryptoService.SetMasterKeyAsync(masterKey);
+                        await SetKeyAndContinueAsync(userKey, true);
                     }
                     else
                     {
@@ -339,12 +357,12 @@ namespace Bit.iOS.Core.Controllers
 
         public async Task PromptBiometricAsync()
         {
-            if (!_biometricLock || !_biometricIntegrityValid)
+            if (!_biometricEnabled || !_biometricIntegrityValid)
             {
                 return;
             }
             var success = await _platformUtilsService.AuthenticateBiometricAsync(null,
-                _pinLock ? AppResources.PIN : AppResources.MasterPassword,
+                _pinEnabled ? AppResources.PIN : AppResources.MasterPassword,
                 () => MasterPasswordCell.TextField.BecomeFirstResponder());
             await _stateService.SetBiometricLockedAsync(!success);
             if (success)
@@ -371,12 +389,12 @@ namespace Bit.iOS.Core.Controllers
             PresentViewController(loginController, true, null);
         }
 
-        private async Task SetKeyAndContinueAsync(SymmetricCryptoKey key, bool masterPassword = false)
+        private async Task SetKeyAndContinueAsync(UserKey userKey, bool masterPassword = false)
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
-                await _cryptoService.SetKeyAsync(key);
+                await _cryptoService.SetUserKeyAsync(userKey);
             }
             DoContinue(masterPassword);
         }
@@ -396,7 +414,7 @@ namespace Bit.iOS.Core.Controllers
         private async Task EnableBiometricsIfNeeded()
         {
             // Re-enable biometrics if initial use
-            if (_biometricLock & !_biometricIntegrityValid)
+            if (_biometricEnabled & !_biometricIntegrityValid)
             {
                 await _biometricService.SetupBiometricAsync(BiometricIntegritySourceKey);
             }
@@ -405,7 +423,7 @@ namespace Bit.iOS.Core.Controllers
         private void InvalidValue()
         {
             var alert = Dialogs.CreateAlert(AppResources.AnErrorHasOccurred,
-                string.Format(null, _pinLock ? AppResources.PIN : AppResources.InvalidMasterPassword),
+                string.Format(null, _pinEnabled ? AppResources.PIN : AppResources.InvalidMasterPassword),
                 AppResources.Ok, (a) =>
                 {
 
@@ -490,7 +508,7 @@ namespace Bit.iOS.Core.Controllers
                     return 0;
                 }
 
-                return (!controller._biometricUnlockOnly && controller._biometricLock) ||
+                return (!controller._biometricUnlockOnly && controller._biometricEnabled) ||
                     controller._passwordReprompt
                     ? 2
                     : 1;

src/iOS.Core/Controllers/LockPasswordViewController.cs

@@ -14,6 +14,7 @@ using Bit.Core.Enums;
 using Bit.App.Pages;
 using Bit.App.Models;
 using Xamarin.Forms;
+using Bit.Core.Services;
 
 namespace Bit.iOS.Core.Controllers
 {
@@ -29,10 +30,9 @@ namespace Bit.iOS.Core.Controllers
         private IPlatformUtilsService _platformUtilsService;
         private IBiometricService _biometricService;
         private IKeyConnectorService _keyConnectorService;
-        private bool _isPinProtected;
+        private PinLockEnum _pinStatus;
-        private bool _isPinProtectedWithKey;
+        private bool _pinEnabled;
-        private bool _pinLock;
+        private bool _biometricEnabled;
-        private bool _biometricLock;
         private bool _biometricIntegrityValid = true;
         private bool _passwordReprompt = false;
         private bool _usesKeyConnector;
@@ -96,25 +96,28 @@ namespace Bit.iOS.Core.Controllers
             if (autofillExtension && await _stateService.GetPasswordRepromptAutofillAsync())
             {
                 _passwordReprompt = true;
-                _isPinProtected = false;
+                _pinStatus = PinLockEnum.Disabled;
-                _isPinProtectedWithKey = false;
+                _pinEnabled = false;
-                _pinLock = false;
+                _biometricEnabled = false;
-                _biometricLock = false;
             }
             else
             {
-                (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
+                _pinStatus = await _vaultTimeoutService.IsPinLockSetAsync();
-                _pinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
+
-                           _isPinProtectedWithKey;
+                var ephemeralPinSet = await _stateService.GetUserKeyPinEphemeralAsync()
-                _biometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() &&
+                    ?? await _stateService.GetPinProtectedKeyAsync();
-                                 await _cryptoService.HasKeyAsync();
+                _pinEnabled = (_pinStatus == PinLockEnum.Transient && ephemeralPinSet != null) ||
+                    _pinStatus == PinLockEnum.Persistent;
+
+                _biometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync()
+                    && await _cryptoService.HasEncryptedUserKeyAsync();
                 _biometricIntegrityValid =
                     await _platformUtilsService.IsBiometricIntegrityValidAsync(BiometricIntegritySourceKey);
                 _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-                _biometricUnlockOnly = _usesKeyConnector && _biometricLock && !_pinLock;
+                _biometricUnlockOnly = _usesKeyConnector && _biometricEnabled && !_pinEnabled;
             }
 
-            if (_pinLock)
+            if (_pinEnabled)
             {
                 BaseNavItem.Title = AppResources.VerifyPIN;
             }
@@ -143,7 +146,7 @@ namespace Bit.iOS.Core.Controllers
 
             if (!_biometricUnlockOnly)
             {
-                MasterPasswordCell.Label.Text = _pinLock ? AppResources.PIN : AppResources.MasterPassword;
+                MasterPasswordCell.Label.Text = _pinEnabled ? AppResources.PIN : AppResources.MasterPassword;
                 MasterPasswordCell.TextField.SecureTextEntry = true;
                 MasterPasswordCell.TextField.ReturnKeyType = UIReturnKeyType.Go;
                 MasterPasswordCell.TextField.ShouldReturn += (UITextField tf) =>
@@ -151,7 +154,7 @@ namespace Bit.iOS.Core.Controllers
                     CheckPasswordAsync().GetAwaiter().GetResult();
                     return true;
                 };
-                if (_pinLock)
+                if (_pinEnabled)
                 {
                     MasterPasswordCell.TextField.KeyboardType = UIKeyboardType.NumberPad;
                 }
@@ -165,7 +168,7 @@ namespace Bit.iOS.Core.Controllers
 
             base.ViewDidLoad();
 
-            if (_biometricLock)
+            if (_biometricEnabled)
             {
                 if (!_biometricIntegrityValid)
                 {
@@ -186,13 +189,13 @@ namespace Bit.iOS.Core.Controllers
             // Users with key connector and without biometric or pin has no MP to unlock with
             if (_usesKeyConnector)
             {
-                if (!(_pinLock || _biometricLock) ||
+                if (!(_pinEnabled || _biometricEnabled) ||
-                    (_biometricLock && !_biometricIntegrityValid))
+                    (_biometricEnabled && !_biometricIntegrityValid))
                 {
                     PromptSSO();
                 }
             }
-            else if (!_biometricLock || !_biometricIntegrityValid)
+            else if (!_biometricEnabled || !_biometricIntegrityValid)
             {
                 MasterPasswordCell.TextField.BecomeFirstResponder();
             }
@@ -204,7 +207,7 @@ namespace Bit.iOS.Core.Controllers
             {
                 var alert = Dialogs.CreateAlert(AppResources.AnErrorHasOccurred,
                     string.Format(AppResources.ValidationFieldRequired,
-                        _pinLock ? AppResources.PIN : AppResources.MasterPassword),
+                        _pinEnabled ? AppResources.PIN : AppResources.MasterPassword),
                     AppResources.Ok);
                 PresentViewController(alert, true, null);
                 return;
@@ -214,33 +217,53 @@ namespace Bit.iOS.Core.Controllers
             var kdfConfig = await _stateService.GetActiveUserCustomDataAsync(a => new KdfConfig(a?.Profile));
             var inputtedValue = MasterPasswordCell.TextField.Text;
 
-            if (_pinLock)
+            if (_pinEnabled)
             {
                 var failed = true;
                 try
                 {
-                    if (_isPinProtected)
+                    EncString userKeyPin = null;
+                    EncString oldPinProtected = null;
+                    if (_pinStatus == PinLockEnum.Persistent)
                     {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                        userKeyPin = await _stateService.GetUserKeyPinAsync();
-                            kdfConfig,
+                        var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
-                            await _stateService.GetPinProtectedKeyAsync());
+                        oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
-                        var encKey = await _cryptoService.GetEncKeyAsync(key);
-                        var protectedPin = await _stateService.GetProtectedPinAsync();
-                        var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                        failed = decPin != inputtedValue;
-                        if (!failed)
-                        {
-                            await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                            await SetKeyAndContinueAsync(key);
                     }
+                    else if (_pinStatus == PinLockEnum.Transient)
+                    {
+                        userKeyPin = await _stateService.GetUserKeyPinEphemeralAsync();
+                        oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                    }
+
+                    UserKey userKey;
+                    if (oldPinProtected != null)
+                    {
+                        userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                            _pinStatus == PinLockEnum.Transient,
+                            inputtedValue,
+                            email,
+                            kdfConfig,
+                            oldPinProtected
+                        );
                     }
                     else
                     {
-                        var key2 = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                        userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
-                            kdfConfig);
+                            inputtedValue,
-                        failed = false;
+                            email,
+                            kdfConfig,
+                            userKeyPin
+                        );
+                    }
+
+                    var protectedPin = await _stateService.GetProtectedPinAsync();
+                    var decryptedPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), userKey);
+                    failed = decryptedPin != inputtedValue;
+                    if (!failed)
+                    {
                         await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                        await SetKeyAndContinueAsync(key2);
+                        await SetKeyAndContinueAsync(userKey);
                     }
                 }
                 catch
@@ -260,33 +283,27 @@ namespace Bit.iOS.Core.Controllers
             }
             else
             {
-                var key2 = await _cryptoService.MakeKeyAsync(inputtedValue, email, kdfConfig);
+                var masterKey = await _cryptoService.MakeMasterKeyAsync(inputtedValue, email, kdfConfig);
                 
-                var storedKeyHash = await _cryptoService.GetKeyHashAsync();
+                var storedPasswordHash = await _cryptoService.GetPasswordHashAsync();
-                if (storedKeyHash == null)
+                if (storedPasswordHash == null)
                 {
                     var oldKey = await _secureStorageService.GetAsync<string>("oldKey");
-                    if (key2.KeyB64 == oldKey)
+                    if (masterKey.KeyB64 == oldKey)
                     {
-                        var localKeyHash = await _cryptoService.HashPasswordAsync(inputtedValue, key2, HashPurpose.LocalAuthorization);
+                        var localPasswordHash = await _cryptoService.HashPasswordAsync(inputtedValue, masterKey, HashPurpose.LocalAuthorization);
                         await _secureStorageService.RemoveAsync("oldKey");
-                        await _cryptoService.SetKeyHashAsync(localKeyHash);
+                        await _cryptoService.SetPasswordHashAsync(localPasswordHash);
                     }
                 }
-                var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(inputtedValue, key2);
+                var passwordValid = await _cryptoService.CompareAndUpdatePasswordHashAsync(inputtedValue, masterKey);
                 if (passwordValid)
                 {
-                    if (_isPinProtected)
-                    {
-                        var protectedPin = await _stateService.GetProtectedPinAsync();
-                        var encKey = await _cryptoService.GetEncKeyAsync(key2);
-                        var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                        var pinKey = await _cryptoService.MakePinKeyAysnc(decPin, email,
-                           kdfConfig);
-                        await _stateService.SetPinProtectedKeyAsync(await _cryptoService.EncryptAsync(key2.Key, pinKey));
-                    }
                     await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                    await SetKeyAndContinueAsync(key2, true);
+
+                    var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                    await _cryptoService.SetMasterKeyAsync(masterKey);
+                    await SetKeyAndContinueAsync(userKey, true);
                 }
                 else
                 {
@@ -303,12 +320,12 @@ namespace Bit.iOS.Core.Controllers
 
         public async Task PromptBiometricAsync()
         {
-            if (!_biometricLock || !_biometricIntegrityValid)
+            if (!_biometricEnabled || !_biometricIntegrityValid)
             {
                 return;
             }
             var success = await _platformUtilsService.AuthenticateBiometricAsync(null,
-                _pinLock ? AppResources.PIN : AppResources.MasterPassword,
+                _pinEnabled ? AppResources.PIN : AppResources.MasterPassword,
                 () => MasterPasswordCell.TextField.BecomeFirstResponder());
             await _stateService.SetBiometricLockedAsync(!success);
             if (success)
@@ -335,12 +352,12 @@ namespace Bit.iOS.Core.Controllers
             PresentViewController(loginController, true, null);
         }
 
-        private async Task SetKeyAndContinueAsync(SymmetricCryptoKey key, bool masterPassword = false)
+        private async Task SetKeyAndContinueAsync(UserKey userKey, bool masterPassword = false)
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
-                await _cryptoService.SetKeyAsync(key);
+                await _cryptoService.SetUserKeyAsync(userKey);
             }
             DoContinue(masterPassword);
         }
@@ -360,7 +377,7 @@ namespace Bit.iOS.Core.Controllers
         private async Task EnableBiometricsIfNeeded()
         {
             // Re-enable biometrics if initial use
-            if (_biometricLock & !_biometricIntegrityValid)
+            if (_biometricEnabled & !_biometricIntegrityValid)
             {
                 await _biometricService.SetupBiometricAsync(BiometricIntegritySourceKey);
             }
@@ -369,7 +386,7 @@ namespace Bit.iOS.Core.Controllers
         private void InvalidValue()
         {
             var alert = Dialogs.CreateAlert(AppResources.AnErrorHasOccurred,
-                string.Format(null, _pinLock ? AppResources.PIN : AppResources.InvalidMasterPassword),
+                string.Format(null, _pinEnabled ? AppResources.PIN : AppResources.InvalidMasterPassword),
                 AppResources.Ok, (a) =>
                     {
 
@@ -444,7 +461,7 @@ namespace Bit.iOS.Core.Controllers
 
             public override nint NumberOfSections(UITableView tableView)
             {
-                return (!_controller._biometricUnlockOnly && _controller._biometricLock) ||
+                return (!_controller._biometricUnlockOnly && _controller._biometricEnabled) ||
                     _controller._passwordReprompt
                     ? 2
                     : 1;

src/iOS.Extension/LoadingViewController.cs

@@ -20,6 +20,7 @@ using Bit.App.Pages;
 using Bit.App.Models;
 using Bit.App.Utilities;
 using Bit.iOS.Core.Views;
+using Bit.Core.Enums;
 
 namespace Bit.iOS.Extension
 {
@@ -519,7 +520,7 @@ namespace Bit.iOS.Extension
                 vm.StartTwoFactorAction = () => DismissViewController(false, () => LaunchTwoFactorFlow(false));
                 vm.UpdateTempPasswordAction = () => DismissViewController(false, () => LaunchUpdateTempPasswordFlow());
                 vm.StartSsoLoginAction = () => DismissViewController(false, () => LaunchLoginSsoFlow());
-                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(email));
+                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, email));
                 vm.LogInSuccessAction = () => DismissLockAndContinue();
                 vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
             }
@@ -532,11 +533,11 @@ namespace Bit.iOS.Extension
             LogoutIfAuthed();
         }
 
-        private void LaunchLoginWithDevice(string email = null)
+        private void LaunchLoginWithDevice(AuthRequestType authRequestType,string email = null)
         {
             var appOptions = new AppOptions { IosExtension = true };
             var app = new App.App(appOptions);
-            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, appOptions);
+            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, authRequestType, appOptions);
             ThemeManager.SetTheme(app.Resources);
             ThemeManager.ApplyResourcesTo(loginWithDevicePage);
             if (loginWithDevicePage.BindingContext is LoginPasswordlessRequestViewModel vm)
@@ -566,6 +567,7 @@ namespace Bit.iOS.Extension
                 vm.StartTwoFactorAction = () => DismissViewController(false, () => LaunchTwoFactorFlow(true));
                 vm.StartSetPasswordAction = () => DismissViewController(false, () => LaunchSetPasswordFlow());
                 vm.UpdateTempPasswordAction = () => DismissViewController(false, () => LaunchUpdateTempPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 vm.SsoAuthSuccessAction = () => DismissLockAndContinue();
                 vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
             }
@@ -588,6 +590,7 @@ namespace Bit.iOS.Extension
             {
                 vm.TwoFactorAuthSuccessAction = () => DismissLockAndContinue();
                 vm.StartSetPasswordAction = () => DismissViewController(false, () => LaunchSetPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 if (authingWithSso)
                 {
                     vm.CloseAction = () => DismissViewController(false, () => LaunchLoginSsoFlow());
@@ -641,5 +644,25 @@ namespace Bit.iOS.Extension
             updateTempPasswordController.ModalPresentationStyle = UIModalPresentationStyle.FullScreen;
             PresentViewController(updateTempPasswordController, true, null);
         }
+
+        private void LaunchDeviceApprovalOptionsFlow()
+        {
+            var loginApproveDevicePage = new LoginApproveDevicePage();
+            var app = new App.App(new AppOptions { IosExtension = true });
+            ThemeManager.SetTheme(app.Resources);
+            ThemeManager.ApplyResourcesTo(loginApproveDevicePage);
+            if (loginApproveDevicePage.BindingContext is LoginApproveDeviceViewModel vm)
+            {
+                vm.LogInWithMasterPasswordAction = () => DismissViewController(false, () => PerformSegue("lockPasswordSegue", this));
+                vm.RequestAdminApprovalAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AdminApproval, vm.Email));
+                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, vm.Email));
+                vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
+            }
+
+            var navigationPage = new NavigationPage(loginApproveDevicePage);
+            var loginApproveDeviceController = navigationPage.CreateViewController();
+            loginApproveDeviceController.ModalPresentationStyle = UIModalPresentationStyle.FullScreen;
+            PresentViewController(loginApproveDeviceController, true, null);
+        }
     }
 }

src/iOS.ShareExtension/LoadingViewController.cs

@@ -339,7 +339,7 @@ namespace Bit.iOS.ShareExtension
                 vm.StartTwoFactorAction = () => DismissAndLaunch(() => LaunchTwoFactorFlow(false));
                 vm.UpdateTempPasswordAction = () => DismissAndLaunch(() => LaunchUpdateTempPasswordFlow());
                 vm.StartSsoLoginAction = () => DismissAndLaunch(() => LaunchLoginSsoFlow());
-                vm.LogInWithDeviceAction = () => DismissAndLaunch(() => LaunchLoginWithDevice(email));
+                vm.LogInWithDeviceAction = () => DismissAndLaunch(() => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, email));
                 vm.LogInSuccessAction = () => { DismissLockAndContinue(); };
                 vm.CloseAction = () => DismissAndLaunch(() => LaunchHomePage());
             }
@@ -348,9 +348,9 @@ namespace Bit.iOS.ShareExtension
             LogoutIfAuthed();
         }
 
-        private void LaunchLoginWithDevice(string email = null)
+        private void LaunchLoginWithDevice(AuthRequestType authRequestType, string email = null)
         {
-            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, _appOptions.Value);
+            var loginWithDevicePage = new LoginPasswordlessRequestPage(email, authRequestType, _appOptions.Value);
             SetupAppAndApplyResources(loginWithDevicePage);
             if (loginWithDevicePage.BindingContext is LoginPasswordlessRequestViewModel vm)
             {
@@ -373,6 +373,7 @@ namespace Bit.iOS.ShareExtension
                 vm.StartTwoFactorAction = () => DismissAndLaunch(() => LaunchTwoFactorFlow(true));
                 vm.StartSetPasswordAction = () => DismissAndLaunch(() => LaunchSetPasswordFlow());
                 vm.UpdateTempPasswordAction = () => DismissAndLaunch(() => LaunchUpdateTempPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 vm.SsoAuthSuccessAction = () => DismissLockAndContinue();
                 vm.CloseAction = () => DismissAndLaunch(() => LaunchHomePage());
             }
@@ -389,6 +390,7 @@ namespace Bit.iOS.ShareExtension
             {
                 vm.TwoFactorAuthSuccessAction = () => DismissLockAndContinue();
                 vm.StartSetPasswordAction = () => DismissAndLaunch(() => LaunchSetPasswordFlow());
+                vm.StartDeviceApprovalOptionsAction = () => DismissViewController(false, () => LaunchDeviceApprovalOptionsFlow());
                 if (authingWithSso)
                 {
                     vm.CloseAction = () => DismissAndLaunch(() => LaunchLoginSsoFlow());
@@ -427,6 +429,26 @@ namespace Bit.iOS.ShareExtension
             NavigateToPage(updateTempPasswordPage);
         }
 
+        private void LaunchDeviceApprovalOptionsFlow()
+        {
+            var loginApproveDevicePage = new LoginApproveDevicePage();
+            var app = new App.App(new AppOptions { IosExtension = true });
+            ThemeManager.SetTheme(app.Resources);
+            ThemeManager.ApplyResourcesTo(loginApproveDevicePage);
+            if (loginApproveDevicePage.BindingContext is LoginApproveDeviceViewModel vm)
+            {
+                vm.LogInWithMasterPasswordAction = () => DismissViewController(false, () => PerformSegue("lockPasswordSegue", this));
+                vm.RequestAdminApprovalAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AdminApproval, vm.Email));
+                vm.LogInWithDeviceAction = () => DismissViewController(false, () => LaunchLoginWithDevice(AuthRequestType.AuthenticateAndUnlock, vm.Email));
+                vm.CloseAction = () => DismissViewController(false, () => LaunchHomePage());
+            }
+
+            var navigationPage = new NavigationPage(loginApproveDevicePage);
+            var loginApproveDeviceController = navigationPage.CreateViewController();
+            loginApproveDeviceController.ModalPresentationStyle = UIModalPresentationStyle.FullScreen;
+            PresentViewController(loginApproveDeviceController, true, null);
+        }
+
         public void Navigate(NavigationTarget navTarget, INavigationParams navParams = null)
         {
             if (ExtNavigationController?.ViewControllers?.Any() ?? false)

test/Core.Test/Services/CipherServiceTests.cs

@@ -29,7 +29,7 @@ namespace Bit.Core.Test.Services
                 .Returns(encFileName);
             sutProvider.GetDependency<ICryptoService>().EncryptToBytesAsync(data.Buffer, Arg.Any<SymmetricCryptoKey>())
                 .Returns(data);
-            sutProvider.GetDependency<ICryptoService>().MakeEncKeyAsync(Arg.Any<SymmetricCryptoKey>()).Returns(new Tuple<SymmetricCryptoKey, EncString>(null, encKey));
+            sutProvider.GetDependency<ICryptoService>().MakeDataEncKeyAsync(Arg.Any<UserKey>()).Returns(new Tuple<SymmetricCryptoKey, EncString>(null, encKey));
             sutProvider.GetDependency<IApiService>().PostCipherAttachmentAsync(cipher.Id, Arg.Any<AttachmentRequest>())
                 .Returns(uploadDataResponse);
 
@@ -50,7 +50,7 @@ namespace Bit.Core.Test.Services
                 .Returns(new EncString(fileName));
             sutProvider.GetDependency<ICryptoService>().EncryptToBytesAsync(data.Buffer, Arg.Any<SymmetricCryptoKey>())
                 .Returns(data);
-            sutProvider.GetDependency<ICryptoService>().MakeEncKeyAsync(Arg.Any<SymmetricCryptoKey>()).Returns(new Tuple<SymmetricCryptoKey, EncString>(null, encKey));
+            sutProvider.GetDependency<ICryptoService>().MakeDataEncKeyAsync(Arg.Any<UserKey>()).Returns(new Tuple<SymmetricCryptoKey, EncString>(null, encKey));
             sutProvider.GetDependency<IApiService>().PostCipherAttachmentAsync(cipher.Id, Arg.Any<AttachmentRequest>())
                 .Throws(new ApiException(new ErrorResponse { StatusCode = statusCode }));
             sutProvider.GetDependency<IApiService>().PostCipherAttachmentLegacyAsync(cipher.Id, Arg.Any<MultipartFormDataContent>())
@@ -70,7 +70,7 @@ namespace Bit.Core.Test.Services
                 .Returns(new EncString(fileName));
             sutProvider.GetDependency<ICryptoService>().EncryptToBytesAsync(data.Buffer, Arg.Any<SymmetricCryptoKey>())
                 .Returns(data);
-            sutProvider.GetDependency<ICryptoService>().MakeEncKeyAsync(Arg.Any<SymmetricCryptoKey>())
+            sutProvider.GetDependency<ICryptoService>().MakeDataEncKeyAsync(Arg.Any<UserKey>())
                 .Returns(new Tuple<SymmetricCryptoKey, EncString>(null, encKey));
             var expectedException = new ApiException(new ErrorResponse { StatusCode = HttpStatusCode.BadRequest });
             sutProvider.GetDependency<IApiService>().PostCipherAttachmentAsync(cipher.Id, Arg.Any<AttachmentRequest>())

test/Core.Test/Services/SendServiceTests.cs

@@ -145,7 +145,7 @@ namespace Bit.Core.Test.Services
             return;
 
             var sendDataDict = sendDatas.ToDictionary(d => d.Id, d => d);
-            sutProvider.GetDependency<ICryptoService>().HasKeyAsync().Returns(true);
+            sutProvider.GetDependency<ICryptoService>().HasUserKeyAsync().Returns(true);
             ServiceContainer.Register("cryptoService", sutProvider.GetDependency<ICryptoService>());
             sutProvider.GetDependency<II18nService>().StringComparer.Returns(StringComparer.CurrentCulture);
             sutProvider.GetDependency<IStateService>().GetActiveUserIdAsync().Returns(userId);