PM-3194 Fix biometrics button to be shown on upgrade when no UserKey is present yet

- returning null from a task thats not async throws

src/Android/MainApplication.cs

@@ -156,9 +156,9 @@ namespace Bit.Droid
                 messagingService, broadcasterService);
             var autofillHandler = new AutofillHandler(stateService, messagingService, clipboardService,
                 platformUtilsService, new LazyResolve<IEventService>());
-            var biometricService = new BiometricService(stateService);
             var cryptoFunctionService = new PclCryptoFunctionService(cryptoPrimitiveService);
             var cryptoService = new CryptoService(stateService, cryptoFunctionService);
+            var biometricService = new BiometricService(stateService, cryptoService);
             var passwordRepromptService = new MobilePasswordRepromptService(platformUtilsService, cryptoService);
 
             ServiceContainer.Register<ISynchronousStorageService>(preferencesStorage);

src/Android/Services/BiometricService.cs

@@ -2,6 +2,7 @@
 using System.Threading.Tasks;
 using Android.OS;
 using Android.Security.Keystore;
+using Bit.App.Services;
 using Bit.Core.Abstractions;
 using Bit.Core.Services;
 using Java.Security;
@@ -9,10 +10,8 @@ using Javax.Crypto;
 
 namespace Bit.Droid.Services
 {
-    public class BiometricService : IBiometricService
+    public class BiometricService : BaseBiometricService
     {
-        private readonly IStateService _stateService;
-
         private const string KeyName = "com.8bit.bitwarden.biometric_integrity";
 
         private const string KeyStoreName = "AndroidKeyStore";
@@ -24,14 +23,14 @@ namespace Bit.Droid.Services
 
         private readonly KeyStore _keystore;
 
-        public BiometricService(IStateService stateService)
+        public BiometricService(IStateService stateService, ICryptoService cryptoService)
+            : base(stateService, cryptoService)
         {
-            _stateService = stateService;
             _keystore = KeyStore.GetInstance(KeyStoreName);
             _keystore.Load(null);
         }
 
-        public async Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null)
+        public override async Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null)
         {
             if (Build.VERSION.SdkInt >= BuildVersionCodes.M)
             {
@@ -41,7 +40,7 @@ namespace Bit.Droid.Services
             return true;
         }
 
-        public async Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null)
+        public override async Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null)
         {
             if (Build.VERSION.SdkInt < BuildVersionCodes.M)
             {

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

@@ -38,16 +38,15 @@ namespace Bit.App.Pages
         private string _masterPassword;
         private string _pin;
         private bool _showPassword;
-        private bool _pinLock;
-        private bool _biometricLock;
+        private PinLockType _pinStatus;
+        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()
         {
@@ -100,10 +99,10 @@ namespace Bit.App.Pages
                 });
         }
 
-        public bool PinLock
+        public bool PinEnabled
         {
-            get => _pinLock;
-            set => SetProperty(ref _pinLock, value);
+            get => _pinEnabled;
+            set => SetProperty(ref _pinEnabled, value);
         }
 
         public bool UsingKeyConnector
@@ -111,10 +110,10 @@ namespace Bit.App.Pages
             get => _usingKeyConnector;
         }
 
-        public bool BiometricLock
+        public bool BiometricEnabled
         {
-            get => _biometricLock;
-            set => SetProperty(ref _biometricLock, value);
+            get => _biometricEnabled;
+            set => SetProperty(ref _biometricEnabled, value);
         }
 
         public bool BiometricIntegrityValid
@@ -162,14 +161,18 @@ namespace Bit.App.Pages
 
         public async Task InitAsync()
         {
-            (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
-            PinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
-                      _isPinProtectedWithKey;
-            BiometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() && await _cryptoService.HasKeyAsync();
+            _pinStatus = await _vaultTimeoutService.GetPinLockTypeAsync();
+
+            var ephemeralPinSet = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync()
+                ?? await _stateService.GetPinProtectedKeyAsync();
+            PinEnabled = (_pinStatus == PinLockType.Transient && ephemeralPinSet != null) ||
+                      _pinStatus == PinLockType.Persistent;
+
+            BiometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync() && await _biometricService.CanUseBiometricsUnlockAsync();
 
             // Users with key connector and without biometric or pin has no MP to unlock with
-            _usingKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-            if (_usingKeyConnector && !(BiometricLock || PinLock))
+            _usingKeyConnector = await _keyConnectorService.GetUsesKeyConnectorAsync();
+            if (_usingKeyConnector && !(BiometricEnabled || PinEnabled))
             {
                 await _vaultTimeoutService.LogOutAsync();
                 return;
@@ -188,7 +191,7 @@ 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 +210,7 @@ namespace Bit.App.Pages
                 }
             }
 
-            if (BiometricLock)
+            if (BiometricEnabled)
             {
                 BiometricIntegrityValid = await _platformUtilsService.IsBiometricIntegrityValidAsync();
                 if (!_biometricIntegrityValid)
@@ -229,14 +232,14 @@ 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 +250,54 @@ 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 == PinLockType.Persistent)
                     {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(Pin, _email,
+                        userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyAsync();
+                        var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
+                        oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
+                    }
+                    else if (_pinStatus == PinLockType.Transient)
+                    {
+                        userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync();
+                        oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                    }
+
+                    UserKey userKey;
+                    if (oldPinProtected != null)
+                    {
+                        userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                            _pinStatus == PinLockType.Transient,
+                            Pin,
+                            _email,
                             kdfConfig,
-                            await _stateService.GetPinProtectedKeyAsync());
-                        var encKey = await _cryptoService.GetEncKeyAsync(key);
-                        var protectedPin = await _stateService.GetProtectedPinAsync();
-                        var decPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), encKey);
-                        failed = decPin != Pin;
-                        if (!failed)
-                        {
-                            Pin = string.Empty;
-                            await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                            await SetKeyAndContinueAsync(key);
-                        }
+                            oldPinProtected
+                        );
                     }
                     else
                     {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(Pin, _email, kdfConfig);
-                        failed = false;
+                        userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
+                            Pin,
+                            _email,
+                            kdfConfig,
+                            userKeyPin
+                        );
+                    }
+
+                    var protectedPin = await _stateService.GetProtectedPinAsync();
+                    var decryptedPin = await _cryptoService.DecryptToUtf8Async(new EncString(protectedPin), userKey);
+                    failed = decryptedPin != Pin;
+                    if (!failed)
+                    {
                         Pin = string.Empty;
                         await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                        await SetKeyAndContinueAsync(key);
+                        await SetUserKeyAndContinueAsync(userKey);
                     }
                 }
                 catch
@@ -295,19 +318,21 @@ namespace Bit.App.Pages
             }
             else
             {
-                var key = await _cryptoService.MakeKeyAsync(MasterPassword, _email, kdfConfig);
-                var storedKeyHash = await _cryptoService.GetKeyHashAsync();
+                var masterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, _email, kdfConfig);
+                var storedKeyHash = await _cryptoService.GetMasterKeyHashAsync();
                 var passwordValid = false;
                 MasterPasswordPolicyOptions enforcedMasterPasswordOptions = null;
 
                 if (storedKeyHash != null)
                 {
-                    passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(MasterPassword, key);
+                    // Offline unlock possible
+                    passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(MasterPassword, masterKey);
                 }
                 else
                 {
+                    // Online unlock required
                     await _deviceActionService.ShowLoadingAsync(AppResources.Loading);
-                    var keyHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.ServerAuthorization);
+                    var keyHash = await _cryptoService.HashMasterKeyAsync(MasterPassword, masterKey, HashPurpose.ServerAuthorization);
                     var request = new PasswordVerificationRequest();
                     request.MasterPasswordHash = keyHash;
 
@@ -316,8 +341,8 @@ namespace Bit.App.Pages
                         var response = await _apiService.PostAccountVerifyPasswordAsync(request);
                         enforcedMasterPasswordOptions = response.MasterPasswordPolicy;
                         passwordValid = true;
-                        var localKeyHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.LocalAuthorization);
-                        await _cryptoService.SetKeyHashAsync(localKeyHash);
+                        var localKeyHash = await _cryptoService.HashMasterKeyAsync(MasterPassword, masterKey, HashPurpose.LocalAuthorization);
+                        await _cryptoService.SetMasterKeyHashAsync(localKeyHash);
                     }
                     catch (Exception e)
                     {
@@ -327,15 +352,6 @@ 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 +361,13 @@ namespace Bit.App.Pages
 
                     MasterPassword = string.Empty;
                     await AppHelpers.ResetInvalidUnlockAttemptsAsync();
-                    await SetKeyAndContinueAsync(key);
+
+                    var userKey = await _cryptoService.DecryptUserKeyWithMasterKeyAsync(masterKey);
+                    await _cryptoService.SetMasterKeyAsync(masterKey);
+                    await SetUserKeyAndContinueAsync(userKey);
 
                     // Re-enable biometrics
-                    if (BiometricLock & !BiometricIntegrityValid)
+                    if (BiometricEnabled & !BiometricIntegrityValid)
                     {
                         await _biometricService.SetupBiometricAsync();
                     }
@@ -425,7 +444,7 @@ 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));
         }
 
@@ -433,26 +452,27 @@ 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)
             {
-                await DoContinueAsync();
+                var userKey = await _cryptoService.GetBiometricUnlockKeyAsync();
+                await SetUserKeyAndContinueAsync(userKey);
             }
         }
 
-        private async Task SetKeyAndContinueAsync(SymmetricCryptoKey key)
+        private async Task SetUserKeyAndContinueAsync(UserKey key)
         {
-            var hasKey = await _cryptoService.HasKeyAsync();
+            var hasKey = await _cryptoService.HasUserKeyAsync();
             if (!hasKey)
             {
-                await _cryptoService.SetKeyAsync(key);
+                await _cryptoService.SetUserKeyAsync(key);
             }
             await DoContinueAsync();
         }

src/App/Pages/Accounts/RegisterPageViewModel.cs

@@ -177,25 +177,25 @@ 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 encKey = await _cryptoService.MakeEncKeyAsync(key);
-            var hashedPassword = await _cryptoService.HashPasswordAsync(MasterPassword, key);
-            var keys = await _cryptoService.MakeKeyPairAsync(encKey.Item1);
+            var newMasterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, Email, kdfConfig);
+            var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(newMasterKey);
+            var hashedPassword = await _cryptoService.HashMasterKeyAsync(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,
-                    EncryptedPrivateKey = keys.Item2.EncryptedString
+                    PublicKey = newPublicKey,
+                    EncryptedPrivateKey = newProtectedPrivateKey.EncryptedString
                 },
                 CaptchaResponse = _captchaToken,
             };

src/App/Pages/Accounts/RemoveMasterPasswordPageViewModel.cs

@@ -30,14 +30,14 @@ namespace Bit.App.Pages
 
         public async Task Init()
         {
-            Organization = await _keyConnectorService.GetManagingOrganization();
+            Organization = await _keyConnectorService.GetManagingOrganizationAsync();
         }
 
         public async Task MigrateAccount()
         {
             await _deviceActionService.ShowLoadingAsync(AppResources.Loading);
 
-            await _keyConnectorService.MigrateUser();
+            await _keyConnectorService.MigrateUserAsync();
             await _syncService.FullSyncAsync(true);
 
             await _deviceActionService.HideLoadingAsync();

src/App/Pages/Accounts/SetPasswordPageViewModel.cs

@@ -165,26 +165,17 @@ 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 masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.ServerAuthorization);
-            var localMasterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key, HashPurpose.LocalAuthorization);
+            var newMasterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, email, kdfConfig);
+            var masterPasswordHash = await _cryptoService.HashMasterKeyAsync(MasterPassword, newMasterKey, HashPurpose.ServerAuthorization);
+            var localMasterPasswordHash = await _cryptoService.HashMasterKeyAsync(MasterPassword, newMasterKey, HashPurpose.LocalAuthorization);
 
-            Tuple<SymmetricCryptoKey, EncString> encKey;
-            var existingEncKey = await _cryptoService.GetEncKeyAsync();
-            if (existingEncKey == null)
-            {
-                encKey = await _cryptoService.MakeEncKeyAsync(key);
-            }
-            else
-            {
-                encKey = await _cryptoService.RemakeEncKeyAsync(key);
-            }
+            var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(newMasterKey);
 
-            var keys = await _cryptoService.MakeKeyPairAsync(encKey.Item1);
+            var (newPublicKey, newProtectedPrivateKey) = 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),
@@ -193,8 +184,8 @@ namespace Bit.App.Pages
                 OrgIdentifier = OrgIdentifier,
                 Keys = new KeysRequest
                 {
-                    PublicKey = keys.Item1,
-                    EncryptedPrivateKey = keys.Item2.EncryptedString
+                    PublicKey = newPublicKey,
+                    EncryptedPrivateKey = newProtectedPrivateKey.EncryptedString
                 }
             };
 
@@ -204,19 +195,20 @@ namespace Bit.App.Pages
                 // Set Password and relevant information
                 await _apiService.SetPasswordAsync(request);
                 await _stateService.SetKdfConfigurationAsync(kdfConfig);
-                await _cryptoService.SetKeyAsync(key);
-                await _cryptoService.SetKeyHashAsync(localMasterPasswordHash);
-                await _cryptoService.SetEncKeyAsync(encKey.Item2.EncryptedString);
-                await _cryptoService.SetEncPrivateKeyAsync(keys.Item2.EncryptedString);
+                await _cryptoService.SetUserKeyAsync(newUserKey);
+                await _cryptoService.SetMasterKeyAsync(newMasterKey);
+                await _cryptoService.SetMasterKeyHashAsync(localMasterPasswordHash);
+                await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(newProtectedUserKey.EncryptedString);
+                await _cryptoService.SetUserPrivateKeyAsync(newProtectedPrivateKey.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
-                    var userEncKey = await _cryptoService.GetEncKeyAsync();
-                    var encryptedKey = await _cryptoService.RsaEncryptAsync(userEncKey.Key, publicKey);
+                    // Grab User Key and encrypt with Org Public Key
+                    var userKey = await _cryptoService.GetUserKeyAsync();
+                    var encryptedKey = await _cryptoService.RsaEncryptAsync(userKey.Key, publicKey);
                     // Request
                     var resetRequest = new OrganizationUserResetPasswordEnrollmentRequest
                     {

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
-            var key = await _cryptoService.MakeKeyAsync(MasterPassword, email, kdfConfig);
-            var masterPasswordHash = await _cryptoService.HashPasswordAsync(MasterPassword, key);
+            // Create new master key and hash new password
+            var masterKey = await _cryptoService.MakeMasterKeyAsync(MasterPassword, email, kdfConfig);
+            var masterPasswordHash = await _cryptoService.HashMasterKeyAsync(MasterPassword, masterKey);
 
-            // Create new encKey for the User
-            var newEncKey = await _cryptoService.RemakeEncKeyAsync(key);
+            // Encrypt user key with new master 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();
@@ -155,7 +155,7 @@ namespace Bit.App.Pages
 
         private async Task UpdatePasswordAsync(string newMasterPasswordHash, string newEncKey)
         {
-            var currentPasswordHash = await _cryptoService.HashPasswordAsync(CurrentMasterPassword, null);
+            var currentPasswordHash = await _cryptoService.HashMasterKeyAsync(CurrentMasterPassword, null);
 
             var request = new PasswordRequest
             {

src/App/Pages/Settings/ExportVaultPageViewModel.cs

@@ -67,7 +67,7 @@ namespace Bit.App.Pages
             _initialized = true;
             FileFormatSelectedIndex = FileFormatOptions.FindIndex(k => k.Key == "json");
             DisablePrivateVaultPolicyEnabled = await _policyService.PolicyAppliesToUser(PolicyType.DisablePersonalVaultExport);
-            UseOTPVerification = await _keyConnectorService.GetUsesKeyConnector();
+            UseOTPVerification = await _keyConnectorService.GetUsesKeyConnectorAsync();
 
             if (UseOTPVerification)
             {
@@ -165,7 +165,7 @@ namespace Bit.App.Pages
                 return;
             }
 
-            var verificationType = await _keyConnectorService.GetUsesKeyConnector()
+            var verificationType = await _keyConnectorService.GetUsesKeyConnectorAsync()
                 ? VerificationType.OTP
                 : VerificationType.MasterPassword;
             if (!await _userVerificationService.VerifyUser(Secret, verificationType))

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

@@ -138,8 +138,8 @@ namespace Bit.App.Pages
                     t.Value != null).ToList();
             }
 
-            var pinSet = await _vaultTimeoutService.IsPinLockSetAsync();
-            _pin = pinSet.Item1 || pinSet.Item2;
+            var pinSet = await _vaultTimeoutService.GetPinLockTypeAsync();
+            _pin = pinSet != PinLockType.Disabled;
             _biometric = await _vaultTimeoutService.IsBiometricLockSetAsync();
             _screenCaptureAllowed = await _stateService.GetScreenCaptureAllowedAsync();
 
@@ -149,7 +149,7 @@ namespace Bit.App.Pages
             }
 
             _showChangeMasterPassword = IncludeLinksWithSubscriptionInfo() &&
-                !await _keyConnectorService.GetUsesKeyConnector();
+                !await _keyConnectorService.GetUsesKeyConnectorAsync();
             _reportLoggingEnabled = await _loggerService.IsEnabled();
             _approvePasswordlessLoginRequests = await _stateService.GetApprovePasswordlessLoginsAsync();
             _shouldConnectToWatch = await _stateService.GetShouldConnectToWatchAsync();
@@ -323,6 +323,7 @@ namespace Bit.App.Pages
             }
             if (oldTimeout != newTimeout)
             {
+                await _cryptoService.RefreshKeysAsync();
                 await Device.InvokeOnMainThreadAsync(BuildList);
             }
         }
@@ -428,7 +429,7 @@ namespace Bit.App.Pages
                 if (!string.IsNullOrWhiteSpace(pin))
                 {
                     var masterPassOnRestart = false;
-                    if (!await _keyConnectorService.GetUsesKeyConnector())
+                    if (!await _keyConnectorService.GetUsesKeyConnectorAsync())
                     {
                         masterPassOnRestart = await _platformUtilsService.ShowDialogAsync(
                             AppResources.PINRequireMasterPasswordRestart, AppResources.UnlockWithPIN,
@@ -437,19 +438,20 @@ 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 key = await _cryptoService.GetKeyAsync();
-                    var pinProtectedKey = await _cryptoService.EncryptAsync(key.Key, pinKey);
+                    var pinKey = await _cryptoService.MakePinKeyAsync(pin, email, kdfConfig);
+                    var userKey = await _cryptoService.GetUserKeyAsync();
+                    var protectedPinKey = 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.SetProtectedPinAsync(encPin.EncryptedString);
-                        await _stateService.SetPinProtectedKeyAsync(pinProtectedKey);
+                        await _stateService.SetPinKeyEncryptedUserKeyEphemeralAsync(protectedPinKey);
                     }
                     else
                     {
-                        await _stateService.SetPinProtectedAsync(pinProtectedKey.EncryptedString);
+                        await _stateService.SetPinKeyEncryptedUserKeyAsync(protectedPinKey);
                     }
                 }
                 else
@@ -459,7 +461,6 @@ namespace Bit.App.Pages
             }
             if (!_pin)
             {
-                await _cryptoService.ClearPinProtectedKeyAsync();
                 await _vaultTimeoutService.ClearAsync();
             }
             BuildList();
@@ -491,7 +492,7 @@ namespace Bit.App.Pages
                 await _stateService.SetBiometricUnlockAsync(null);
             }
             await _stateService.SetBiometricLockedAsync(false);
-            await _cryptoService.ToggleKeyAsync();
+            await _cryptoService.RefreshKeysAsync();
             BuildList();
         }
 

src/App/Pages/TabsPage.cs

@@ -94,7 +94,7 @@ namespace Bit.App.Pages
                 }
             });
             await UpdateVaultButtonTitleAsync();
-            if (await _keyConnectorService.UserNeedsMigration())
+            if (await _keyConnectorService.UserNeedsMigrationAsync())
             {
                 _messagingService.Send("convertAccountToKeyConnector");
             }

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/Pages/Vault/CipherAddEditPage.xaml.cs

@@ -176,7 +176,7 @@ namespace Bit.App.Pages
                 }
             });
             // Hide password reprompt option if using key connector
-            _passwordPrompt.IsVisible = !await _keyConnectorService.GetUsesKeyConnector();
+            _passwordPrompt.IsVisible = !await _keyConnectorService.GetUsesKeyConnectorAsync();
         }
 
         protected override void OnDisappearing()

src/App/Services/BaseBiometricService.cs

@@ -0,0 +1,25 @@
+using System.Threading.Tasks;
+using Bit.Core.Abstractions;
+
+namespace Bit.App.Services
+{
+    public abstract class BaseBiometricService : IBiometricService
+    {
+        protected readonly IStateService _stateService;
+        protected readonly ICryptoService _cryptoService;
+
+        protected BaseBiometricService(IStateService stateService, ICryptoService cryptoService)
+        {
+            _stateService = stateService;
+            _cryptoService = cryptoService;
+        }
+
+        public async Task<bool> CanUseBiometricsUnlockAsync()
+        {
+            return await _cryptoService.HasEncryptedUserKeyAsync() || await _stateService.GetKeyEncryptedAsync() != null;
+        }
+
+        public abstract Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null);
+        public abstract Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null);
+    }
+}

src/App/Services/MobilePasswordRepromptService.cs

@@ -44,7 +44,7 @@ namespace Bit.App.Services
         public async Task<bool> Enabled()
         {
             var keyConnectorService = ServiceContainer.Resolve<IKeyConnectorService>("keyConnectorService");
-            return !await keyConnectorService.GetUsesKeyConnector();
+            return !await keyConnectorService.GetUsesKeyConnectorAsync();
         }
     }
 }

src/App/Utilities/AccountManagement/AccountsManager.cs

@@ -206,6 +206,7 @@ namespace Bit.App.Utilities.AccountManagement
 
         private async Task AddAccountAsync()
         {
+            await AppHelpers.ClearServiceCacheAsync();
             await Device.InvokeOnMainThreadAsync(() =>
             {
                 Options.HideAccountSwitcher = false;

src/App/Utilities/VerificationActionsFlowHelper.cs

@@ -107,7 +107,7 @@ namespace Bit.App.Utilities
 
         public async Task ValidateAndExecuteAsync()
         {
-            var verificationType = await _keyConnectorService.GetUsesKeyConnector()
+            var verificationType = await _keyConnectorService.GetUsesKeyConnectorAsync()
                 ? VerificationType.OTP
                 : VerificationType.MasterPassword;
 
@@ -121,7 +121,7 @@ namespace Bit.App.Utilities
                     }
 
                     var parameters = GetParameters();
-                    parameters.Secret = await _cryptoService.HashPasswordAsync(password, null);
+                    parameters.Secret = await _cryptoService.HashMasterKeyAsync(password, null);
                     parameters.VerificationType = VerificationType.MasterPassword;
                     await ExecuteAsync(parameters);
                     break;

src/Core/Abstractions/IApiService.cs

@@ -70,7 +70,7 @@ namespace Bit.Core.Abstractions
         Task<OrganizationAutoEnrollStatusResponse> GetOrganizationAutoEnrollStatusAsync(string identifier);
         Task PutOrganizationUserResetPasswordEnrollmentAsync(string orgId, string userId,
             OrganizationUserResetPasswordEnrollmentRequest request);
-        Task<KeyConnectorUserKeyResponse> GetUserKeyFromKeyConnector(string keyConnectorUrl);
+        Task<KeyConnectorUserKeyResponse> GetMasterKeyFromKeyConnectorAsync(string keyConnectorUrl);
         Task PostUserKeyToKeyConnector(string keyConnectorUrl, KeyConnectorUserKeyRequest request);
         Task PostSetKeyConnectorKey(SetKeyConnectorKeyRequest request);
         Task PostConvertToKeyConnector();

src/Core/Abstractions/IBiometricService.cs

@@ -4,6 +4,7 @@ namespace Bit.Core.Abstractions
 {
     public interface IBiometricService
     {
+        Task<bool> CanUseBiometricsUnlockAsync();
         Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null);
         Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null);
     }

src/Core/Abstractions/ICryptoService.cs

@@ -9,49 +9,56 @@ 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 RefreshKeysAsync();
+        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<UserKey> GetAutoUnlockKeyAsync(string userId = null);
+        Task<bool> HasAutoUnlockKeyAsync(string userId = null);
+        Task<UserKey> GetBiometricUnlockKeyAsync(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);
+        Task<UserKey> DecryptUserKeyWithMasterKeyAsync(MasterKey masterKey, EncString encUserKey = null, string userId = null);
+        Task<Tuple<SymmetricCryptoKey, EncString>> MakeDataEncKeyAsync(SymmetricCryptoKey key);
+        Task<string> HashMasterKeyAsync(string password, MasterKey key, HashPurpose hashPurpose = HashPurpose.ServerAuthorization);
+        Task SetMasterKeyHashAsync(string keyHash);
+        Task<string> GetMasterKeyHashAsync();
+        Task ClearMasterKeyHashAsync(string userId = null);
+        Task<bool> CompareAndUpdateKeyHashAsync(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[]> GetUserPublicKeyAsync();
+        Task SetUserPrivateKeyAsync(string encPrivateKey);
+        Task<byte[]> GetUserPrivateKeyAsync();
+        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<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();
+        Task<UserKey> DecryptAndMigrateOldPinKeyAsync(bool masterPasswordOnRestart, string pin, string email, KdfConfig kdfConfig, EncString oldPinKey);
     }
 }

src/Core/Abstractions/IKeyConnectorService.cs

@@ -6,11 +6,11 @@ namespace Bit.Core.Abstractions
 {
     public interface IKeyConnectorService
     {
-        Task SetUsesKeyConnector(bool usesKeyConnector);
-        Task<bool> GetUsesKeyConnector();
-        Task<bool> UserNeedsMigration();
-        Task MigrateUser();
-        Task GetAndSetKey(string url);
-        Task<Organization> GetManagingOrganization();
+        Task SetUsesKeyConnectorAsync(bool usesKeyConnector);
+        Task<bool> GetUsesKeyConnectorAsync();
+        Task<bool> UserNeedsMigrationAsync();
+        Task MigrateUserAsync();
+        Task GetAndSetMasterKeyAsync(string url);
+        Task<Organization> GetManagingOrganizationAsync();
     }
 }

src/Core/Abstractions/IStateService.cs

@@ -13,6 +13,14 @@ 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> GetMasterKeyEncryptedUserKeyAsync(string userId = null);
+        Task SetMasterKeyEncryptedUserKeyAsync(string value, string userId = null);
+        Task<UserKey> GetUserKeyAutoUnlockAsync(string userId = null);
+        Task SetUserKeyAutoUnlockAsync(UserKey value, string userId = null);
         Task<string> GetActiveUserIdAsync();
         Task<string> GetActiveUserEmailAsync();
         Task<T> GetActiveUserCustomDataAsync<T>(Func<Account, T> dataMapper);
@@ -27,6 +35,8 @@ namespace Bit.Core.Abstractions
         Task<EnvironmentUrlData> GetPreAuthEnvironmentUrlsAsync();
         Task SetPreAuthEnvironmentUrlsAsync(EnvironmentUrlData value);
         Task<EnvironmentUrlData> GetEnvironmentUrlsAsync(string userId = null);
+        Task<UserKey> GetUserKeyBiometricUnlockAsync(string userId = null);
+        Task SetUserKeyBiometricUnlockAsync(UserKey value, string userId = null);
         Task<bool?> GetBiometricUnlockAsync(string userId = null);
         Task SetBiometricUnlockAsync(bool? value, string userId = null);
         Task<bool> GetBiometricLockedAsync(string userId = null);
@@ -36,22 +46,16 @@ 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> GetPinKeyEncryptedUserKeyAsync(string userId = null);
+        Task SetPinKeyEncryptedUserKeyAsync(EncString value, string userId = null);
+        Task<EncString> GetPinKeyEncryptedUserKeyEphemeralAsync(string userId = null);
+        Task SetPinKeyEncryptedUserKeyEphemeralAsync(EncString value, string userId = null);
         Task SetProtectedPinAsync(string value, string userId = null);
-        Task<string> GetPinProtectedAsync(string userId = null);
-        Task SetPinProtectedAsync(string value, string userId = null);
-        Task<EncString> GetPinProtectedKeyAsync(string userId = null);
-        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);
@@ -176,5 +180,24 @@ namespace Bit.Core.Abstractions
         void SetLocale(string locale);
         ConfigResponse GetConfigs();
         void SetConfigs(ConfigResponse value);
+        [Obsolete("Use GetPinKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        Task<string> GetPinProtectedAsync(string userId = null);
+        [Obsolete("Use SetPinKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        Task SetPinProtectedAsync(string value, string userId = null);
+        [Obsolete("Use GetPinKeyEncryptedUserKeyEphemeralAsync instead, left for migration purposes")]
+        Task<EncString> GetPinProtectedKeyAsync(string userId = null);
+        [Obsolete("Use SetPinKeyEncryptedUserKeyEphemeralAsync instead, left for migration purposes")]
+        Task SetPinProtectedKeyAsync(EncString value, string userId = null);
+        [Obsolete("Use GetMasterKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        Task<string> GetEncKeyEncryptedAsync(string userId = null);
+        [Obsolete("Use SetMasterKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        Task SetEncKeyEncryptedAsync(string value, string userId = null);
+        [Obsolete("Left for migration purposes")]
+        Task SetKeyEncryptedAsync(string value, string userId = null);
+
+        [Obsolete("Use GetUserKeyAutoUnlock instead, left for migration purposes")]
+        Task<string> GetKeyEncryptedAsync(string userId = null);
+        [Obsolete("Use GetMasterKeyAsync instead, left for migration purposes")]
+        Task<SymmetricCryptoKey> GetKeyDecryptedAsync(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<PinLockType> GetPinLockTypeAsync(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
     {
@@ -79,6 +81,9 @@
 
         public static string VaultTimeoutKey(string userId) => $"vaultTimeout_{userId}";
         public static string VaultTimeoutActionKey(string userId) => $"vaultTimeoutAction_{userId}";
+        public static string MasterKeyEncryptedUserKeyKey(string userId) => $"masterKeyEncryptedUserKey_{userId}";
+        public static string UserKeyAutoUnlockKey(string userId) => $"autoUnlock_{userId}";
+        public static string UserKeyBiometricUnlockKey(string userId) => $"biometricUnlock_{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 +92,10 @@
         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 KeyHashKey(string userId) => $"keyHash_{userId}";
-        public static string PinProtectedKey(string userId) => $"pinProtectedKey_{userId}";
+        public static string PinKeyEncryptedUserKeyKey(string userId) => $"pinKeyEncryptedUserKey_{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 +124,11 @@
         public static string PushCurrentTokenKey(string userId) => $"pushCurrentToken_{userId}";
         public static string ShouldConnectToWatchKey(string userId) => $"shouldConnectToWatch_{userId}";
         public static string ScreenCaptureAllowedKey(string userId) => $"screenCaptureAllowed_{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/Models/Domain/Account.cs

@@ -117,9 +117,14 @@ namespace Bit.Core.Models.Domain
 
         public class AccountVolatileData
         {
-            public SymmetricCryptoKey Key;
-            public EncString PinProtectedKey;
+            public UserKey UserKey;
+            public MasterKey MasterKey;
+            public EncString PinKeyEncryptedUserKeyEphemeral;
             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/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/Services/ApiService.cs

@@ -485,7 +485,7 @@ namespace Bit.Core.Services
 
         #region Key Connector
 
-        public async Task<KeyConnectorUserKeyResponse> GetUserKeyFromKeyConnector(string keyConnectorUrl)
+        public async Task<KeyConnectorUserKeyResponse> GetMasterKeyFromKeyConnectorAsync(string keyConnectorUrl)
         {
             using (var requestMessage = new HttpRequestMessage())
             {

src/Core/Services/AuthService.cs

@@ -30,7 +30,7 @@ namespace Bit.Core.Services
         private readonly bool _setCryptoKeys;
 
         private readonly LazyResolve<IWatchDeviceService> _watchDeviceService = new LazyResolve<IWatchDeviceService>();
-        private SymmetricCryptoKey _key;
+        private MasterKey _masterKey;
 
         private string _authedUserId;
         private MasterPasswordPolicyOptions _masterPasswordPolicy;
@@ -46,8 +46,6 @@ namespace Bit.Core.Services
             II18nService i18nService,
             IPlatformUtilsService platformUtilsService,
             IMessagingService messagingService,
-            IVaultTimeoutService vaultTimeoutService,
-            IKeyConnectorService keyConnectorService,
             IPasswordGenerationService passwordGenerationService,
             IPolicyService policyService,
             bool setCryptoKeys = true)
@@ -61,7 +59,6 @@ namespace Bit.Core.Services
             _i18nService = i18nService;
             _platformUtilsService = platformUtilsService;
             _messagingService = messagingService;
-            _keyConnectorService = keyConnectorService;
             _passwordGenerationService = passwordGenerationService;
             _policyService = policyService;
             _setCryptoKeys = setCryptoKeys;
@@ -145,8 +142,8 @@ namespace Bit.Core.Services
             SelectedTwoFactorProviderType = null;
             _2faForcePasswordResetReason = null;
             var key = await MakePreloginKeyAsync(masterPassword, email);
-            var hashedPassword = await _cryptoService.HashPasswordAsync(masterPassword, key);
-            var localHashedPassword = await _cryptoService.HashPasswordAsync(masterPassword, key, HashPurpose.LocalAuthorization);
+            var hashedPassword = await _cryptoService.HashMasterKeyAsync(masterPassword, key);
+            var localHashedPassword = await _cryptoService.HashMasterKeyAsync(masterPassword, key, HashPurpose.LocalAuthorization);
             var result = await LogInHelperAsync(email, hashedPassword, localHashedPassword, null, null, null, key, null, null, null, captchaToken);
 
             if (await RequirePasswordChangeAsync(email, masterPassword))
@@ -199,7 +196,7 @@ namespace Bit.Core.Services
         {
             var decKey = await _cryptoService.RsaDecryptAsync(userKeyCiphered, 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,
+            return await LogInHelperAsync(email, accessCode, Encoding.UTF8.GetString(decPasswordHash), null, null, null, new MasterKey(decKey), null, null,
                 null, null, authRequestId: authRequestId);
         }
 
@@ -216,7 +213,7 @@ 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()
@@ -236,8 +233,8 @@ namespace Bit.Core.Services
         {
             SelectedTwoFactorProviderType = null;
             var key = await MakePreloginKeyAsync(masterPassword, email);
-            var hashedPassword = await _cryptoService.HashPasswordAsync(masterPassword, key);
-            var localHashedPassword = await _cryptoService.HashPasswordAsync(masterPassword, key, HashPurpose.LocalAuthorization);
+            var hashedPassword = await _cryptoService.HashMasterKeyAsync(masterPassword, key);
+            var localHashedPassword = await _cryptoService.HashMasterKeyAsync(masterPassword, key, HashPurpose.LocalAuthorization);
             return await LogInHelperAsync(email, hashedPassword, localHashedPassword, null, null, null, key, twoFactorProvider,
                 twoFactorToken, remember);
         }
@@ -337,7 +334,7 @@ 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 +353,11 @@ 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 +423,7 @@ 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;
@@ -470,24 +467,27 @@ 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.SetMasterKeyHashAsync(localHashedPassword);
                 }
 
                 if (code == null || tokenResponse.Key != null)
                 {
                     if (tokenResponse.KeyConnectorUrl != null)
                     {
-                        await _keyConnectorService.GetAndSetKey(tokenResponse.KeyConnectorUrl);
+                        await _keyConnectorService.GetAndSetMasterKeyAsync(tokenResponse.KeyConnectorUrl);
                     }
 
-                    await _cryptoService.SetEncKeyAsync(tokenResponse.Key);
+                    await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(tokenResponse.Key);
+
+                    if (masterKey != null)
+                    {
+                        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 +505,26 @@ namespace Bit.Core.Services
                         catch { }
                     }
 
-                    await _cryptoService.SetEncPrivateKeyAsync(tokenResponse.PrivateKey);
+                    await _cryptoService.SetUserPrivateKeyAsync(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 keyConnectorRequest = new KeyConnectorUserKeyRequest(k.EncKeyB64);
-                    await _cryptoService.SetKeyAsync(k);
+                    var newMasterKey = await _cryptoService.MakeMasterKeyAsync(
+                        Convert.ToBase64String(password),
+                        _tokenService.GetEmail(),
+                        tokenResponse.KdfConfig);
 
-                    var encKey = await _cryptoService.MakeEncKeyAsync(k);
-                    await _cryptoService.SetEncKeyAsync(encKey.Item2.EncryptedString);
-                    var keyPair = await _cryptoService.MakeKeyPairAsync();
+                    var keyConnectorRequest = new KeyConnectorUserKeyRequest(newMasterKey.EncKeyB64);
+
+                    var (newUserKey, newProtectedUserKey) = await _cryptoService.EncryptUserKeyWithMasterKeyAsync(newMasterKey);
+
+                    await _cryptoService.SetUserKeyAsync(newUserKey);
+                    await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(newProtectedUserKey.EncryptedString);
+                    await _cryptoService.SetMasterKeyAsync(newMasterKey);
+
+                    var (newPublicKey, newProtectedPrivateKey) = await _cryptoService.MakeKeyPairAsync();
 
                     try
                     {
@@ -530,11 +537,11 @@ namespace Bit.Core.Services
 
                     var keys = new KeysRequest
                     {
-                        PublicKey = keyPair.Item1,
-                        EncryptedPrivateKey = keyPair.Item2.EncryptedString
+                        PublicKey = newPublicKey,
+                        EncryptedPrivateKey = newProtectedPrivateKey.EncryptedString
                     };
                     var setPasswordRequest = new SetKeyConnectorKeyRequest(
-                        encKey.Item2.EncryptedString, keys, tokenResponse.KdfConfig, orgId
+                        newProtectedPrivateKey.EncryptedString, keys, tokenResponse.KdfConfig, orgId
                     );
                     await _apiService.PostSetKeyConnectorKey(setPasswordRequest);
                 }
@@ -549,7 +556,7 @@ namespace Bit.Core.Services
 
         private void ClearState()
         {
-            _key = null;
+            _masterKey = null;
             Email = null;
             CaptchaToken = null;
             MasterPasswordHash = null;
@@ -590,7 +597,7 @@ 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 deviceId = await _appIdService.GetAppIdAsync();

src/Core/Services/CipherService.cs

@@ -249,8 +249,7 @@ namespace Bit.Core.Services
             {
                 try
                 {
-                    var hashKey = await _cryptoService.HasKeyAsync();
-                    if (!hashKey)
+                    if (!await _cryptoService.HasUserKeyAsync())
                     {
                         throw new Exception("No key.");
                     }
@@ -557,9 +556,9 @@ namespace Bit.Core.Services
 
         public async Task<Cipher> SaveAttachmentRawWithServerAsync(Cipher cipher, string filename, byte[] data)
         {
-            var orgKey = await _cryptoService.GetOrgKeyAsync(cipher.OrganizationId);
-            var encFileName = await _cryptoService.EncryptAsync(filename, orgKey);
-            var (attachmentKey, orgEncAttachmentKey) = await _cryptoService.MakeEncKeyAsync(orgKey);
+            var (attachmentKey, protectedAttachmentKey, encKey) = await MakeAttachmentKeyAsync(cipher.OrganizationId);
+
+            var encFileName = await _cryptoService.EncryptAsync(filename, encKey);
             var encFileData = await _cryptoService.EncryptToBytesAsync(data, attachmentKey);
 
             CipherResponse response;
@@ -567,7 +566,7 @@ namespace Bit.Core.Services
             {
                 var request = new AttachmentRequest
                 {
-                    Key = orgEncAttachmentKey.EncryptedString,
+                    Key = protectedAttachmentKey.EncryptedString,
                     FileName = encFileName.EncryptedString,
                     FileSize = encFileData.Buffer.Length,
                 };
@@ -578,7 +577,7 @@ 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();
@@ -796,6 +795,14 @@ namespace Bit.Core.Services
 
         // Helpers
 
+        private async Task<Tuple<SymmetricCryptoKey, EncString, SymmetricCryptoKey>> MakeAttachmentKeyAsync(string organizationId)
+        {
+            var encryptionKey = await _cryptoService.GetOrgKeyAsync(organizationId)
+                ?? (SymmetricCryptoKey)await _cryptoService.GetUserKeyWithLegacySupportAsync();
+            var (attachmentKey, protectedAttachmentKey) = await _cryptoService.MakeDataEncKeyAsync(encryptionKey);
+            return new Tuple<SymmetricCryptoKey, EncString, SymmetricCryptoKey>(attachmentKey, protectedAttachmentKey, encryptionKey);
+        }
+
         private async Task ShareAttachmentWithServerAsync(AttachmentView attachmentView, string cipherId,
             string organizationId)
         {
@@ -807,14 +814,16 @@ 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);
-            var dataEncKey = await _cryptoService.MakeEncKeyAsync(key);
-            var encData = await _cryptoService.EncryptToBytesAsync(decBytes, dataEncKey.Item1);
+
+            var (attachmentKey, protectedAttachmentKey, encKey) = await MakeAttachmentKeyAsync(organizationId);
+
+            var encFileName = await _cryptoService.EncryptAsync(attachmentView.FileName, encKey);
+            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 StreamContent(new MemoryStream(encData.Buffer)), "data", encFileName.EncryptedString);
+            fd.Add(new StringContent(protectedAttachmentKey.EncryptedString), "key");
+            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/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

@@ -24,14 +24,14 @@ namespace Bit.Core.Services
             _organizationService = organizationService;
         }
 
-        public async Task GetAndSetKey(string url)
+        public async Task GetAndSetMasterKeyAsync(string url)
         {
             try
             {
-                var userKeyResponse = await _apiService.GetUserKeyFromKeyConnector(url);
-                var keyArr = Convert.FromBase64String(userKeyResponse.Key);
-                var k = new SymmetricCryptoKey(keyArr);
-                await _cryptoService.SetKeyAsync(k);
+                var masterKeyResponse = await _apiService.GetMasterKeyFromKeyConnectorAsync(url);
+                var masterKeyArr = Convert.FromBase64String(masterKeyResponse.Key);
+                var masterKey = new MasterKey(masterKeyArr);
+                await _cryptoService.SetMasterKeyAsync(masterKey);
             }
             catch (Exception e)
             {
@@ -39,17 +39,17 @@ namespace Bit.Core.Services
             }
         }
 
-        public async Task SetUsesKeyConnector(bool usesKeyConnector)
+        public async Task SetUsesKeyConnectorAsync(bool usesKeyConnector)
         {
             await _stateService.SetUsesKeyConnectorAsync(usesKeyConnector);
         }
 
-        public async Task<bool> GetUsesKeyConnector()
+        public async Task<bool> GetUsesKeyConnectorAsync()
         {
             return await _stateService.GetUsesKeyConnectorAsync();
         }
 
-        public async Task<Organization> GetManagingOrganization()
+        public async Task<Organization> GetManagingOrganizationAsync()
         {
             var orgs = await _organizationService.GetAllAsync();
             return orgs.Find(o =>
@@ -57,14 +57,14 @@ namespace Bit.Core.Services
                 !o.IsAdmin);
         }
 
-        public async Task MigrateUser()
+        public async Task MigrateUserAsync()
         {
-            var organization = await GetManagingOrganization();
-            var key = await _cryptoService.GetKeyAsync();
+            var organization = await GetManagingOrganizationAsync();
+            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)
@@ -75,11 +75,11 @@ namespace Bit.Core.Services
             await _apiService.PostConvertToKeyConnector();
         }
 
-        public async Task<bool> UserNeedsMigration()
+        public async Task<bool> UserNeedsMigrationAsync()
         {
             var loggedInUsingSso = await _tokenService.GetIsExternal();
-            var requiredByOrganization = await GetManagingOrganization() != null;
-            var userIsNotUsingKeyConnector = !await GetUsesKeyConnector();
+            var requiredByOrganization = await GetManagingOrganizationAsync() != null;
+            var userIsNotUsingKeyConnector = !await GetUsesKeyConnectorAsync();
 
             return loggedInUsingSso && requiredByOrganization && userIsNotUsingKeyConnector;
         }

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

@@ -241,6 +241,19 @@ namespace Bit.Core.Services
             ))?.Settings?.EnvironmentUrls;
         }
 
+        public async Task<UserKey> GetUserKeyBiometricUnlockAsync(string userId = null)
+        {
+            var keyB64 = await _storageMediatorService.GetAsync<string>(
+                await ComposeKeyAsync(Constants.UserKeyBiometricUnlockKey, userId), true);
+            return keyB64 == null ? null : new UserKey(Convert.FromBase64String(keyB64));
+        }
+
+        public async Task SetUserKeyBiometricUnlockAsync(UserKey value, string userId = null)
+        {
+            await _storageMediatorService.SaveAsync(
+                await ComposeKeyAsync(Constants.UserKeyBiometricUnlockKey, userId), value?.KeyB64, true);
+        }
+
         public async Task<bool?> GetBiometricUnlockAsync(string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -302,12 +315,70 @@ 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> GetMasterKeyEncryptedUserKeyAsync(string userId = null)
+        {
+            return await _storageMediatorService.GetAsync<string>(
+                await ComposeKeyAsync(Constants.MasterKeyEncryptedUserKeyKey, userId), false);
+        }
+
+        public async Task SetMasterKeyEncryptedUserKeyAsync(string value, string userId = null)
+        {
+            await _storageMediatorService.SaveAsync(
+                await ComposeKeyAsync(Constants.MasterKeyEncryptedUserKeyKey, userId), value, false);
+        }
+
+        public async Task<UserKey> GetUserKeyAutoUnlockAsync(string userId = null)
+        {
+            var keyB64 = await _storageMediatorService.GetAsync<string>(
+                await ComposeKeyAsync(Constants.UserKeyAutoUnlockKey, userId), true);
+            return keyB64 == null ? null : new UserKey(Convert.FromBase64String(keyB64));
+        }
+
+        public async Task SetUserKeyAutoUnlockAsync(UserKey value, string userId = null)
+        {
+            await _storageMediatorService.SaveAsync(
+                await ComposeKeyAsync(Constants.UserKeyAutoUnlockKey, userId), value?.KeyB64, true);
+        }
+
         public async Task<bool> CanAccessPremiumAsync(string userId = null)
         {
             if (userId == null)
             {
                 userId = await GetActiveUserIdAsync();
             }
+
             if (!await IsAuthenticatedAsync(userId))
             {
                 return false;
@@ -353,36 +424,36 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.ProtectedPinKey(reconciledOptions.UserId), value, reconciledOptions);
         }
 
-        public async Task<string> GetPinProtectedAsync(string userId = null)
+        public async Task<EncString> GetPinKeyEncryptedUserKeyAsync(string userId = null)
         {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultStorageOptionsAsync());
-            return await GetValueAsync<string>(Constants.PinProtectedKey(reconciledOptions.UserId), reconciledOptions);
+            var key = await _storageMediatorService.GetAsync<string>(
+                await ComposeKeyAsync(Constants.PinKeyEncryptedUserKeyKey, userId), false);
+            return key != null ? new EncString(key) : null;
         }
 
-        public async Task SetPinProtectedAsync(string value, string userId = null)
+        public async Task SetPinKeyEncryptedUserKeyAsync(EncString value, string userId = null)
         {
-            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
-                await GetDefaultStorageOptionsAsync());
-            await SetValueAsync(Constants.PinProtectedKey(reconciledOptions.UserId), value, reconciledOptions);
+            await _storageMediatorService.SaveAsync(
+                await ComposeKeyAsync(Constants.PinKeyEncryptedUserKeyKey, userId), value?.EncryptedString, false);
         }
 
-        public async Task<EncString> GetPinProtectedKeyAsync(string userId = null)
+        public async Task<EncString> GetPinKeyEncryptedUserKeyEphemeralAsync(string userId = null)
         {
             return (await GetAccountAsync(
                 ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
-            ))?.VolatileData?.PinProtectedKey;
+            ))?.VolatileData?.PinKeyEncryptedUserKeyEphemeral;
         }
 
-        public async Task SetPinProtectedKeyAsync(EncString value, string userId = null)
+        public async Task SetPinKeyEncryptedUserKeyEphemeralAsync(EncString value, string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
                 await GetDefaultInMemoryOptionsAsync());
             var account = await GetAccountAsync(reconciledOptions);
-            account.VolatileData.PinProtectedKey = value;
+            account.VolatileData.PinKeyEncryptedUserKeyEphemeral = value;
             await SaveAccountAsync(account, reconciledOptions);
         }
 
+
         public async Task SetKdfConfigurationAsync(KdfConfig config, string userId = null)
         {
             var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
@@ -395,35 +466,6 @@ 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 +481,6 @@ 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)
         {
@@ -1447,28 +1476,31 @@ namespace Bit.Core.Services
             }
 
             // Non-state storage
-            await SetProtectedPinAsync(null, userId);
-            await SetPinProtectedAsync(null, userId);
-            await SetKeyEncryptedAsync(null, userId);
-            await SetKeyHashAsync(null, userId);
-            await SetEncKeyEncryptedAsync(null, userId);
-            await SetOrgKeysEncryptedAsync(null, userId);
-            await SetPrivateKeyEncryptedAsync(null, userId);
-            await SetLastActiveTimeAsync(null, userId);
-            await SetPreviousPageInfoAsync(null, userId);
-            await SetInvalidUnlockAttemptsAsync(null, userId);
-            await SetLocalDataAsync(null, userId);
-            await SetEncryptedCiphersAsync(null, userId);
-            await SetEncryptedCollectionsAsync(null, userId);
-            await SetLastSyncAsync(null, userId);
-            await SetEncryptedFoldersAsync(null, userId);
-            await SetEncryptedPoliciesAsync(null, userId);
-            await SetUsesKeyConnectorAsync(null, userId);
-            await SetOrganizationsAsync(null, userId);
-            await SetEncryptedPasswordGenerationHistoryAsync(null, userId);
-            await SetEncryptedSendsAsync(null, userId);
-            await SetSettingsAsync(null, userId);
-            await SetApprovePasswordlessLoginsAsync(null, userId);
+            await Task.WhenAll(
+                SetUserKeyAutoUnlockAsync(null, userId),
+                SetUserKeyBiometricUnlockAsync(null, userId),
+                SetProtectedPinAsync(null, userId),
+                SetKeyHashAsync(null, userId),
+                SetOrgKeysEncryptedAsync(null, userId),
+                SetPrivateKeyEncryptedAsync(null, userId),
+                SetLastActiveTimeAsync(null, userId),
+                SetPreviousPageInfoAsync(null, userId),
+                SetInvalidUnlockAttemptsAsync(null, userId),
+                SetLocalDataAsync(null, userId),
+                SetEncryptedCiphersAsync(null, userId),
+                SetEncryptedCollectionsAsync(null, userId),
+                SetLastSyncAsync(null, userId),
+                SetEncryptedFoldersAsync(null, userId),
+                SetEncryptedPoliciesAsync(null, userId),
+                SetUsesKeyConnectorAsync(null, userId),
+                SetOrganizationsAsync(null, userId),
+                SetEncryptedPasswordGenerationHistoryAsync(null, userId),
+                SetEncryptedSendsAsync(null, userId),
+                SetSettingsAsync(null, userId),
+                SetApprovePasswordlessLoginsAsync(null, userId),
+                SetEncKeyEncryptedAsync(null, userId),
+                SetKeyEncryptedAsync(null, userId),
+                SetPinProtectedAsync(null, userId));
         }
 
         private async Task ScaffoldNewAccountAsync(Account account)
@@ -1656,5 +1688,79 @@ namespace Bit.Core.Services
             await SetValueAsync(Constants.LastUserShouldConnectToWatchKey,
                 shouldConnect ?? await GetShouldConnectToWatchAsync(), await GetDefaultStorageOptionsAsync());
         }
+
+        [Obsolete("Use GetPinKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        public async Task<string> GetPinProtectedAsync(string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            return await GetValueAsync<string>(Constants.PinProtectedKey(reconciledOptions.UserId), reconciledOptions);
+        }
+
+        [Obsolete("Use SetPinKeyEncryptedUserKeyAsync instead")]
+        public async Task SetPinProtectedAsync(string value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultStorageOptionsAsync());
+            await SetValueAsync(Constants.PinProtectedKey(reconciledOptions.UserId), value, reconciledOptions);
+        }
+
+        [Obsolete("Use GetPinKeyEncryptedUserKeyEphemeralAsync instead, left for migration purposes")]
+        public async Task<EncString> GetPinProtectedKeyAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.PinProtectedKey;
+        }
+
+        [Obsolete("Use SetPinKeyEncryptedUserKeyEphemeralAsync instead")]
+        public async Task SetPinProtectedKeyAsync(EncString value, string userId = null)
+        {
+            var reconciledOptions = ReconcileOptions(new StorageOptions { UserId = userId },
+                await GetDefaultInMemoryOptionsAsync());
+            var account = await GetAccountAsync(reconciledOptions);
+            account.VolatileData.PinProtectedKey = value;
+            await SaveAccountAsync(account, reconciledOptions);
+        }
+
+        [Obsolete("Use GetMasterKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        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("Use SetMasterKeyEncryptedUserKeyAsync instead, left for migration purposes")]
+        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("Left for migration purposes")]
+        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("Use GetUserKeyAutoUnlock instead, left for migration purposes")]
+        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("Use GetMasterKeyAsync instead, left for migration purposes")]
+        public async Task<SymmetricCryptoKey> GetKeyDecryptedAsync(string userId = null)
+        {
+            return (await GetAccountAsync(
+                ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultInMemoryOptionsAsync())
+            ))?.VolatileData?.Key;
+        }
     }
 }

src/Core/Services/SyncService.cs

@@ -327,8 +327,8 @@ namespace Bit.Core.Services
                 }
                 return;
             }
-            await _cryptoService.SetEncKeyAsync(response.Key);
-            await _cryptoService.SetEncPrivateKeyAsync(response.PrivateKey);
+            await _cryptoService.SetMasterKeyEncryptedUserKeyAsync(response.Key);
+            await _cryptoService.SetUserPrivateKeyAsync(response.PrivateKey);
             await _cryptoService.SetOrgKeysAsync(response.Organizations);
             await _stateService.SetSecurityStampAsync(response.SecurityStamp);
             var organizations = response.Organizations.ToDictionary(o => o.Id, o => new OrganizationData(o));
@@ -337,7 +337,7 @@ namespace Bit.Core.Services
             await _stateService.SetNameAsync(response.Name);
             await _stateService.SetPersonalPremiumAsync(response.Premium);
             await _stateService.SetAvatarColorAsync(response.AvatarColor);
-            await _keyConnectorService.SetUsesKeyConnector(response.UsesKeyConnector);
+            await _keyConnectorService.SetUsesKeyConnectorAsync(response.UsesKeyConnector);
         }
 
         private async Task SyncFoldersAsync(string userId, List<FolderResponse> response)

src/Core/Services/VaultTimeoutService.cs

@@ -1,12 +1,17 @@
 using System;
-using System.Linq;
 using System.Threading.Tasks;
 using Bit.Core.Abstractions;
 using Bit.Core.Enums;
-using Bit.Core.Models.Domain;
 
 namespace Bit.Core.Services
 {
+    public enum PinLockType
+    {
+        Disabled,
+        Persistent,
+        Transient
+    }
+
     public class VaultTimeoutService : IVaultTimeoutService
     {
         private readonly ICryptoService _cryptoService;
@@ -54,15 +59,26 @@ namespace Bit.Core.Services
 
         public async Task<bool> IsLockedAsync(string userId = null)
         {
-            var hasKey = await _cryptoService.HasKeyAsync(userId);
-            if (hasKey)
+            var biometricSet = await IsBiometricLockSetAsync(userId);
+            if (biometricSet && await _stateService.GetBiometricLockedAsync(userId))
             {
-                var biometricSet = await IsBiometricLockSetAsync(userId);
-                if (biometricSet && await _stateService.GetBiometricLockedAsync(userId))
+                return true;
+            }
+
+            if (!await _cryptoService.HasUserKeyAsync(userId))
+            {
+                if (await _cryptoService.HasAutoUnlockKeyAsync(userId))
+                {
+                    await _cryptoService.SetUserKeyAsync(await _cryptoService.GetAutoUnlockKeyAsync(userId));
+                }
+                else
                 {
                     return true;
                 }
             }
+
+            // Check again to verify auto key was set
+            var hasKey = await _cryptoService.HasUserKeyAsync(userId);
             return !hasKey;
         }
 
@@ -163,13 +179,15 @@ namespace Bit.Core.Services
                 userId = await _stateService.GetActiveUserIdAsync();
             }
 
-            if (await _keyConnectorService.GetUsesKeyConnector())
+            if (await _keyConnectorService.GetUsesKeyConnectorAsync())
             {
-                var (isPinProtected, isPinProtectedWithKey) = await IsPinLockSetAsync(userId);
-                var pinLock = (isPinProtected && await _stateService.GetPinProtectedKeyAsync(userId) != null) ||
-                              isPinProtectedWithKey;
+                var pinStatus = await GetPinLockTypeAsync(userId);
+                var ephemeralPinSet = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync()
+                    ?? await _stateService.GetPinProtectedKeyAsync();
+                var pinEnabled = (pinStatus == PinLockType.Transient && ephemeralPinSet != null) ||
+                          pinStatus == PinLockType.Persistent;
 
-                if (!pinLock && !await IsBiometricLockSetAsync())
+                if (!pinEnabled && !await IsBiometricLockSetAsync())
                 {
                     await LogOutAsync(userInitiated, userId);
                     return;
@@ -187,10 +205,11 @@ namespace Bit.Core.Services
                 }
             }
             await Task.WhenAll(
-                _cryptoService.ClearKeyAsync(userId),
+                _cryptoService.ClearUserKeyAsync(userId),
+                _cryptoService.ClearMasterKeyAsync(userId),
+                _stateService.SetUserKeyAutoUnlockAsync(null, userId),
                 _cryptoService.ClearOrgKeysAsync(true, userId),
-                _cryptoService.ClearKeyPairAsync(true, userId),
-                _cryptoService.ClearEncKeyAsync(true, userId));
+                _cryptoService.ClearKeyPairAsync(true, userId));
 
             if (isActiveAccount)
             {
@@ -214,15 +233,27 @@ namespace Bit.Core.Services
         {
             await _stateService.SetVaultTimeoutAsync(timeout);
             await _stateService.SetVaultTimeoutActionAsync(action);
-            await _cryptoService.ToggleKeyAsync();
+            await _cryptoService.RefreshKeysAsync();
             await _tokenService.ToggleTokensAsync();
         }
 
-        public async Task<Tuple<bool, bool>> IsPinLockSetAsync(string userId = null)
+        public async Task<PinLockType> GetPinLockTypeAsync(string userId = null)
         {
-            var protectedPin = await _stateService.GetProtectedPinAsync(userId);
-            var pinProtectedKey = await _stateService.GetPinProtectedAsync(userId);
-            return new Tuple<bool, bool>(protectedPin != null, pinProtectedKey != null);
+            // we can't depend on only the protected pin being set because old
+            // versions only used it for MP on Restart
+            var isPinEnabled = await _stateService.GetProtectedPinAsync(userId) != null;
+            var hasUserKeyPin = await _stateService.GetPinKeyEncryptedUserKeyAsync(userId) != null;
+            var hasOldUserKeyPin = await _stateService.GetPinProtectedAsync(userId) != null;
+
+            if (hasUserKeyPin || hasOldUserKeyPin)
+            {
+                return PinLockType.Persistent;
+            }
+            else if (isPinEnabled && !hasUserKeyPin && !hasOldUserKeyPin)
+            {
+                return PinLockType.Transient;
+            }
+            return PinLockType.Disabled;
         }
 
         public async Task<bool> IsBiometricLockSetAsync(string userId = null)
@@ -233,8 +264,7 @@ namespace Bit.Core.Services
 
         public async Task ClearAsync(string userId = null)
         {
-            await _stateService.SetPinProtectedKeyAsync(null, userId);
-            await _stateService.SetProtectedPinAsync(null, userId);
+            await _cryptoService.ClearPinKeysAsync(userId);
         }
 
         public async Task<int?> GetVaultTimeout(string userId = null)

src/Core/Utilities/ServiceContainer.cs

@@ -78,8 +78,8 @@ namespace Bit.Core.Utilities
             var passwordGenerationService = new PasswordGenerationService(cryptoService, stateService, cryptoFunctionService, policyService);
             var totpService = new TotpService(cryptoFunctionService);
             var authService = new AuthService(cryptoService, cryptoFunctionService, apiService, stateService,
-                tokenService, appIdService, i18nService, platformUtilsService, messagingService, vaultTimeoutService,
-                keyConnectorService, passwordGenerationService, policyService);
+                tokenService, appIdService, i18nService, platformUtilsService, messagingService,
+                passwordGenerationService, policyService);
             var exportService = new ExportService(folderService, cipherService, cryptoService);
             var auditService = new AuditService(cryptoFunctionService, apiService);
             var environmentService = new EnvironmentService(apiService, stateService, conditionedRunner);

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 bool _isPinProtectedWithKey;
-        private bool _pinLock;
-        private bool _biometricLock;
+        private PinLockType _pinStatus;
+        private bool _pinEnabled;
+        private bool _biometricEnabled;
         private bool _biometricIntegrityValid = true;
         private bool _passwordReprompt = false;
         private bool _usesKeyConnector;
@@ -85,7 +86,7 @@ namespace Bit.iOS.Core.Controllers
         }
 
         public abstract UITableView TableView { get; }
-        
+
         public override async void ViewDidLoad()
         {
             _vaultTimeoutService = ServiceContainer.Resolve<IVaultTimeoutService>("vaultTimeoutService");
@@ -103,25 +104,28 @@ namespace Bit.iOS.Core.Controllers
             if (autofillExtension && await _stateService.GetPasswordRepromptAutofillAsync())
             {
                 _passwordReprompt = true;
-                _isPinProtected = false;
-                _isPinProtectedWithKey = false;
-                _pinLock = false;
-                _biometricLock = false;
+                _pinStatus = PinLockType.Disabled;
+                _pinEnabled = false;
+                _biometricEnabled = false;
             }
             else
             {
-                (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
-                _pinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
-                           _isPinProtectedWithKey;
-                _biometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() &&
-                                 await _cryptoService.HasKeyAsync();
+                _pinStatus = await _vaultTimeoutService.GetPinLockTypeAsync();
+
+                var ephemeralPinSet = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync()
+                    ?? await _stateService.GetPinProtectedKeyAsync();
+                _pinEnabled = (_pinStatus == PinLockType.Transient && ephemeralPinSet != null) ||
+                    _pinStatus == PinLockType.Persistent;
+
+                _biometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync()
+                    && await _cryptoService.HasEncryptedUserKeyAsync();
                 _biometricIntegrityValid =
                     await _platformUtilsService.IsBiometricIntegrityValidAsync(BiometricIntegritySourceKey);
-                _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-                _biometricUnlockOnly = _usesKeyConnector && _biometricLock && !_pinLock;
+                _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnectorAsync();
+                _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)
                 {
@@ -198,18 +202,18 @@ 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) ||
-                    (_biometricLock && !_biometricIntegrityValid))
+                if (!(_pinEnabled || _biometricEnabled) ||
+                    (_biometricEnabled && !_biometricIntegrityValid))
                 {
                     PromptSSO();
                 }
             }
-            else if (!_biometricLock || !_biometricIntegrityValid)
+            else if (!_biometricEnabled || !_biometricIntegrityValid)
             {
                 MasterPasswordCell.TextField.BecomeFirstResponder();
             }
         }
-        
+
         protected async Task CheckPasswordAsync()
         {
             if (_checkingPassword)
@@ -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 == PinLockType.Persistent)
                         {
-                            var key = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                            userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyAsync();
+                            var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
+                            oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
+                        }
+                        else if (_pinStatus == PinLockType.Transient)
+                        {
+                            userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync();
+                            oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                        }
+
+                        UserKey userKey;
+                        if (oldPinProtected != null)
+                        {
+                            userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                                _pinStatus == PinLockType.Transient,
+                                inputtedValue,
+                                email,
                                 kdfConfig,
-                                await _stateService.GetPinProtectedKeyAsync());
-                            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);
-                            }
+                                oldPinProtected
+                            );
                         }
                         else
                         {
-                            var key2 = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
-                                kdfConfig);
-                            failed = false;
+                            userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
+                                inputtedValue,
+                                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();
-                    if (storedKeyHash == null)
+                    var storedPasswordHash = await _cryptoService.GetMasterKeyHashAsync();
+                    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.HashMasterKeyAsync(inputtedValue, masterKey, HashPurpose.LocalAuthorization);
                             await _secureStorageService.RemoveAsync("oldKey");
-                            await _cryptoService.SetKeyHashAsync(localKeyHash);
+                            await _cryptoService.SetMasterKeyHashAsync(localPasswordHash);
                         }
                     }
-                    var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(inputtedValue, key2);
+                    var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(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

@@ -1,18 +1,19 @@
 using System;
-using UIKit;
-using Foundation;
-using Bit.iOS.Core.Views;
-using Bit.App.Resources;
-using Bit.iOS.Core.Utilities;
-using Bit.App.Abstractions;
-using Bit.Core.Abstractions;
-using Bit.Core.Utilities;
 using System.Threading.Tasks;
-using Bit.App.Utilities;
-using Bit.Core.Models.Domain;
-using Bit.Core.Enums;
-using Bit.App.Pages;
+using Bit.App.Abstractions;
 using Bit.App.Models;
+using Bit.App.Pages;
+using Bit.App.Resources;
+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.Forms;
 
 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 bool _isPinProtectedWithKey;
-        private bool _pinLock;
-        private bool _biometricLock;
+        private PinLockType _pinStatus;
+        private bool _pinEnabled;
+        private bool _biometricEnabled;
         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;
-                _isPinProtectedWithKey = false;
-                _pinLock = false;
-                _biometricLock = false;
+                _pinStatus = PinLockType.Disabled;
+                _pinEnabled = false;
+                _biometricEnabled = false;
             }
             else
             {
-                (_isPinProtected, _isPinProtectedWithKey) = await _vaultTimeoutService.IsPinLockSetAsync();
-                _pinLock = (_isPinProtected && await _stateService.GetPinProtectedKeyAsync() != null) ||
-                           _isPinProtectedWithKey;
-                _biometricLock = await _vaultTimeoutService.IsBiometricLockSetAsync() &&
-                                 await _cryptoService.HasKeyAsync();
+                _pinStatus = await _vaultTimeoutService.GetPinLockTypeAsync();
+
+                var ephemeralPinSet = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync()
+                    ?? await _stateService.GetPinProtectedKeyAsync();
+                _pinEnabled = (_pinStatus == PinLockType.Transient && ephemeralPinSet != null) ||
+                    _pinStatus == PinLockType.Persistent;
+
+                _biometricEnabled = await _vaultTimeoutService.IsBiometricLockSetAsync()
+                    && await _cryptoService.HasEncryptedUserKeyAsync();
                 _biometricIntegrityValid =
                     await _platformUtilsService.IsBiometricIntegrityValidAsync(BiometricIntegritySourceKey);
-                _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnector();
-                _biometricUnlockOnly = _usesKeyConnector && _biometricLock && !_pinLock;
+                _usesKeyConnector = await _keyConnectorService.GetUsesKeyConnectorAsync();
+                _biometricUnlockOnly = _usesKeyConnector && _biometricEnabled && !_pinEnabled;
             }
 
-            if (_pinLock)
+            if (_pinEnabled)
             {
                 BaseNavItem.Title = AppResources.VerifyPIN;
             }
@@ -126,7 +129,7 @@ namespace Bit.iOS.Core.Controllers
             {
                 BaseNavItem.Title = AppResources.VerifyMasterPassword;
             }
-            
+
             BaseCancelButton.Title = AppResources.Cancel;
 
             if (_biometricUnlockOnly)
@@ -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) ||
-                    (_biometricLock && !_biometricIntegrityValid))
+                if (!(_pinEnabled || _biometricEnabled) ||
+                    (_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 == PinLockType.Persistent)
                     {
-                        var key = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
+                        userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyAsync();
+                        var oldEncryptedKey = await _stateService.GetPinProtectedAsync();
+                        oldPinProtected = oldEncryptedKey != null ? new EncString(oldEncryptedKey) : null;
+                    }
+                    else if (_pinStatus == PinLockType.Transient)
+                    {
+                        userKeyPin = await _stateService.GetPinKeyEncryptedUserKeyEphemeralAsync();
+                        oldPinProtected = await _stateService.GetPinProtectedKeyAsync();
+                    }
+
+                    UserKey userKey;
+                    if (oldPinProtected != null)
+                    {
+                        userKey = await _cryptoService.DecryptAndMigrateOldPinKeyAsync(
+                            _pinStatus == PinLockType.Transient,
+                            inputtedValue,
+                            email,
                             kdfConfig,
-                            await _stateService.GetPinProtectedKeyAsync());
-                        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);
-                        }
+                            oldPinProtected
+                        );
                     }
                     else
                     {
-                        var key2 = await _cryptoService.MakeKeyFromPinAsync(inputtedValue, email,
-                            kdfConfig);
-                        failed = false;
+                        userKey = await _cryptoService.DecryptUserKeyWithPinAsync(
+                            inputtedValue,
+                            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 storedKeyHash = await _cryptoService.GetKeyHashAsync();
-                if (storedKeyHash == null)
+                var masterKey = await _cryptoService.MakeMasterKeyAsync(inputtedValue, email, kdfConfig);
+
+                var storedPasswordHash = await _cryptoService.GetMasterKeyHashAsync();
+                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.HashMasterKeyAsync(inputtedValue, masterKey, HashPurpose.LocalAuthorization);
                         await _secureStorageService.RemoveAsync("oldKey");
-                        await _cryptoService.SetKeyHashAsync(localKeyHash);
+                        await _cryptoService.SetMasterKeyHashAsync(localPasswordHash);
                     }
                 }
-                var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(inputtedValue, key2);
+                var passwordValid = await _cryptoService.CompareAndUpdateKeyHashAsync(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) =>
                     {
 
@@ -378,7 +395,7 @@ namespace Bit.iOS.Core.Controllers
                     });
             PresentViewController(alert, true, null);
         }
-        
+
         private async Task LogOutAsync()
         {
             await AppHelpers.LogOutAsync(await _stateService.GetActiveUserIdAsync());
@@ -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.Core/Services/BiometricService.cs

@@ -1,20 +1,19 @@
 using System.Threading.Tasks;
+using Bit.App.Services;
 using Bit.Core.Abstractions;
 using Foundation;
 using LocalAuthentication;
 
 namespace Bit.iOS.Core.Services
 {
-    public class BiometricService : IBiometricService
+    public class BiometricService : BaseBiometricService
     {
-        private IStateService _stateService;
-
-        public BiometricService(IStateService stateService)
+        public BiometricService(IStateService stateService, ICryptoService cryptoService)
+            : base(stateService, cryptoService)
         {
-            _stateService = stateService;
         }
 
-        public async Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null)
+        public override async Task<bool> SetupBiometricAsync(string bioIntegritySrcKey = null)
         {
             if (bioIntegritySrcKey == null)
             {
@@ -30,7 +29,7 @@ namespace Bit.iOS.Core.Services
             return true;
         }
 
-        public async Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null)
+        public override async Task<bool> IsSystemBiometricIntegrityValidAsync(string bioIntegritySrcKey = null)
         {
             var state = GetState();
             if (state == null)

src/iOS.Core/Utilities/iOSCoreHelpers.cs

@@ -112,9 +112,9 @@ namespace Bit.iOS.Core.Utilities
             var clipboardService = new ClipboardService(stateService);
             var platformUtilsService = new MobilePlatformUtilsService(deviceActionService, clipboardService,
                 messagingService, broadcasterService);
-            var biometricService = new BiometricService(stateService);
             var cryptoFunctionService = new PclCryptoFunctionService(cryptoPrimitiveService);
             var cryptoService = new CryptoService(stateService, cryptoFunctionService);
+            var biometricService = new BiometricService(stateService, cryptoService);
             var passwordRepromptService = new MobilePasswordRepromptService(platformUtilsService, cryptoService);
 
             ServiceContainer.Register<ISynchronousStorageService>(preferencesStorage);

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);