Authenticated encryption for enterprise secrets (#1078)

app/MindWork AI Studio/Tools/EnterpriseEncryption.cs

@@ -13,25 +13,68 @@ namespace AIStudio.Tools;
 /// is designed to prevent casual exposure of API keys in configuration files. It
 /// also protects against accidental leaks while sharing configuration snippets,
 /// as the encrypted values cannot be decrypted without the secret key.
+/// <br/><br/>
+/// Both formats use the same secret. "ENC:v2:" is authenticated: AES-256-GCM refuses
+/// every value which was encrypted with another secret or changed afterward. "ENC:v1:"
+/// uses AES-256-CBC without authentication, so a wrong secret passes its padding check
+/// in about one of 256 cases; decoding the result strictly as UTF-8 catches nearly all
+/// of those. Versions before v26.10.1 read only v1, which is why AI Studio still writes
+/// it when asked to.
 /// </remarks>
 public sealed class EnterpriseEncryption
 {
     /// <summary>
-    /// The number of iterations to derive the key and IV from the password.
+    /// The number of iterations to derive the key and IV of a v1 value from the password.
     /// We use a higher iteration count here because the secret is static
     /// (not regenerated each startup like the IPC encryption).
     /// </summary>
-    private const int ITERATIONS = 10_000;
+    private const int V1_ITERATIONS = 10_000;
 
     /// <summary>
-    /// The length of the salt in bytes.
+    /// The length of the salt in bytes, in both formats.
     /// </summary>
     private const int SALT_LENGTH = 16;
 
     /// <summary>
-    /// The prefix for encrypted values.
+    /// The length of the AES-GCM nonce of a v2 value in bytes.
     /// </summary>
-    private const string PREFIX = "ENC:v1:";
+    private const int V2_NONCE_LENGTH = 12;
+
+    /// <summary>
+    /// The length of the AES-GCM authentication tag of a v2 value in bytes.
+    /// </summary>
+    private const int V2_TAG_LENGTH = 16;
+
+    /// <summary>
+    /// The prefix all encrypted values share, whatever their format.
+    /// </summary>
+    private const string ENCRYPTED_PREFIX = "ENC:";
+
+    /// <summary>
+    /// The prefix of v1 values.
+    /// </summary>
+    private const string PREFIX_V1 = "ENC:v1:";
+
+    /// <summary>
+    /// The prefix of v2 values.
+    /// </summary>
+    private const string PREFIX_V2 = "ENC:v2:";
+
+    /// <summary>
+    /// What HKDF binds the key of a v2 value to, so that the key serves no other purpose.
+    /// </summary>
+    private static readonly byte[] V2_KEY_INFO = "MindWork AI Studio ENC:v2"u8.ToArray();
+
+    /// <summary>
+    /// The prefix is authenticated together with the ciphertext, so a v2 payload counts under
+    /// this prefix only.
+    /// </summary>
+    private static readonly byte[] V2_ASSOCIATED_DATA = Encoding.UTF8.GetBytes(PREFIX_V2);
+
+    /// <summary>
+    /// Decodes UTF-8 and throws on invalid bytes instead of replacing them.
+    /// </summary>
+    private static readonly UTF8Encoding STRICT_UTF8 = new(encoderShouldEmitUTF8Identifier: false, throwOnInvalidBytes: true);
 
     private readonly ILogger<EnterpriseEncryption> logger;
     private readonly byte[]? secretKey;
@@ -79,16 +122,21 @@ public sealed class EnterpriseEncryption
     }
 
     /// <summary>
-    /// Checks if the given value is encrypted (has the encryption prefix).
+    /// Checks if the given value is encrypted, in whatever format.
     /// </summary>
+    /// <remarks>
+    /// A format which only a newer version of AI Studio knows counts as encrypted, too. Such a
+    /// value cannot be decrypted here, and that is what the user has to learn, rather than that
+    /// it was stored in plaintext.
+    /// </remarks>
     /// <param name="value">The value to check.</param>
     /// <returns>True if the value starts with the encryption prefix; otherwise, false.</returns>
-    public static bool IsEncrypted(string? value) => value?.StartsWith(PREFIX, StringComparison.Ordinal) ?? false;
+    public static bool IsEncrypted(string? value) => value?.StartsWith(ENCRYPTED_PREFIX, StringComparison.Ordinal) ?? false;
 
     /// <summary>
     /// Tries to decrypt an encrypted value.
     /// </summary>
-    /// <param name="encryptedValue">The encrypted value (with ENC:v1: prefix).</param>
+    /// <param name="encryptedValue">The encrypted value, with the ENC:v1: or ENC:v2: prefix.</param>
     /// <param name="decryptedValue">When successful, contains the decrypted plaintext.</param>
     /// <returns>True if decryption was successful; otherwise, false.</returns>
     public bool TryDecrypt(string encryptedValue, out string decryptedValue)
@@ -108,35 +156,26 @@ public sealed class EnterpriseEncryption
 
         try
         {
-            // Extract the base64-encoded data after the prefix:
-            var base64Data = encryptedValue[PREFIX.Length..];
-            var encryptedBytes = Convert.FromBase64String(base64Data);
-            if (encryptedBytes.Length < SALT_LENGTH + 1)
+            byte[]? decryptedBytes;
+            if (encryptedValue.StartsWith(PREFIX_V2, StringComparison.Ordinal))
+                decryptedBytes = this.DecryptV2(Convert.FromBase64String(encryptedValue[PREFIX_V2.Length..]));
+            else if (encryptedValue.StartsWith(PREFIX_V1, StringComparison.Ordinal))
+                decryptedBytes = this.DecryptV1(Convert.FromBase64String(encryptedValue[PREFIX_V1.Length..]));
+            else
             {
-                this.logger.LogWarning("Cannot decrypt: Encrypted data is too short.");
+                this.logger.LogWarning("Cannot decrypt: The value uses an encryption format which this version of AI Studio does not know. A newer version may have encrypted it.");
                 return false;
             }
 
-            // Extract salt and encrypted content:
-            var salt = encryptedBytes[..SALT_LENGTH];
-            var cipherText = encryptedBytes[SALT_LENGTH..];
-
-            // Derive key and IV using PBKDF2:
-            using var keyDerivation = new Rfc2898DeriveBytes(this.secretKey!, salt, ITERATIONS, HashAlgorithmName.SHA512);
-            var key = keyDerivation.GetBytes(32); // AES-256
-            var iv = keyDerivation.GetBytes(16);  // AES block size
-
-            // Decrypt using AES-256-CBC:
-            using var aes = Aes.Create();
-            aes.Key = key;
-            aes.IV = iv;
-            aes.Mode = CipherMode.CBC;
-            aes.Padding = PaddingMode.PKCS7;
-
-            using var decryptor = aes.CreateDecryptor();
-            var decryptedBytes = decryptor.TransformFinalBlock(cipherText, 0, cipherText.Length);
-            decryptedValue = Encoding.UTF8.GetString(decryptedBytes);
+            if (decryptedBytes is null)
+                return false;
 
+            //
+            // AI Studio always encrypted valid UTF-8, so decoding strictly never refuses a genuine
+            // value. It refuses the random bytes, though, which a wrong secret yields for a v1 value
+            // whenever the padding happens to check out:
+            //
+            decryptedValue = STRICT_UTF8.GetString(decryptedBytes);
             return true;
         }
         catch (FormatException ex)
@@ -149,15 +188,21 @@ public sealed class EnterpriseEncryption
             this.logger.LogWarning(ex, "Failed to decrypt value. The encryption secret may be incorrect.");
             return false;
         }
+        catch (DecoderFallbackException ex)
+        {
+            this.logger.LogWarning(ex, "Failed to decrypt value, because the result is no text. The encryption secret may be incorrect.");
+            return false;
+        }
     }
 
     /// <summary>
     /// Encrypts a plaintext value.
     /// </summary>
     /// <param name="plaintext">The plaintext to encrypt.</param>
+    /// <param name="format">The format to write. A v2 value is authenticated, but only AI Studio v26.10.1 and later can read it.</param>
     /// <param name="encryptedValue">When successful, contains the encrypted value with prefix.</param>
     /// <returns>True if encryption was successful; otherwise, false.</returns>
-    public bool TryEncrypt(string plaintext, out string encryptedValue)
+    public bool TryEncrypt(string plaintext, EnterpriseEncryptionFormat format, out string encryptedValue)
     {
         encryptedValue = string.Empty;
         if (!this.IsAvailable)
@@ -168,33 +213,21 @@ public sealed class EnterpriseEncryption
 
         try
         {
-            // Generate a random salt:
-            var salt = RandomNumberGenerator.GetBytes(SALT_LENGTH);
-
-            // Derive key and IV using PBKDF2:
-            using var keyDerivation = new Rfc2898DeriveBytes(this.secretKey!, salt, ITERATIONS, HashAlgorithmName.SHA512);
-            var key = keyDerivation.GetBytes(32); // AES-256
-            var iv = keyDerivation.GetBytes(16);  // AES block size
-
-            // Encrypt using AES-256-CBC:
-            using var aes = Aes.Create();
-            aes.Key = key;
-            aes.IV = iv;
-            aes.Mode = CipherMode.CBC;
-            aes.Padding = PaddingMode.PKCS7;
-
-            using var encryptor = aes.CreateEncryptor();
             var plaintextBytes = Encoding.UTF8.GetBytes(plaintext);
-            var cipherText = encryptor.TransformFinalBlock(plaintextBytes, 0, plaintextBytes.Length);
+            switch (format)
+            {
+                case EnterpriseEncryptionFormat.V1:
+                    encryptedValue = this.EncryptV1(plaintextBytes);
+                    return true;
 
-            // Combine salt and ciphertext
-            var combined = new byte[SALT_LENGTH + cipherText.Length];
-            Array.Copy(salt, 0, combined, 0, SALT_LENGTH);
-            Array.Copy(cipherText, 0, combined, SALT_LENGTH, cipherText.Length);
+                case EnterpriseEncryptionFormat.V2:
+                    encryptedValue = this.EncryptV2(plaintextBytes);
+                    return true;
 
-            // Encode to base64 and add the prefix:
-            encryptedValue = PREFIX + Convert.ToBase64String(combined);
-            return true;
+                default:
+                    this.logger.LogWarning($"Cannot encrypt: The encryption format '{format}' is unknown.");
+                    return false;
+            }
         }
         catch (CryptographicException ex)
         {
@@ -208,4 +241,118 @@ public sealed class EnterpriseEncryption
     /// </summary>
     /// <returns>A base64-encoded 32-byte secret key.</returns>
     public static string GenerateSecret() => Convert.ToBase64String(RandomNumberGenerator.GetBytes(32));
+
+    /// <summary>
+    /// Encrypts into a v1 value: the salt, followed by the AES-256-CBC ciphertext.
+    /// </summary>
+    private string EncryptV1(byte[] plaintextBytes)
+    {
+        // Generate a random salt:
+        var salt = RandomNumberGenerator.GetBytes(SALT_LENGTH);
+
+        // Encrypt using AES-256-CBC:
+        using var aes = this.CreateAesV1(salt);
+        using var encryptor = aes.CreateEncryptor();
+        var cipherText = encryptor.TransformFinalBlock(plaintextBytes, 0, plaintextBytes.Length);
+
+        // Combine salt and ciphertext, encode to base64, and add the prefix:
+        byte[] combined = [..salt, ..cipherText];
+        return PREFIX_V1 + Convert.ToBase64String(combined);
+    }
+
+    /// <summary>
+    /// Decrypts the payload of a v1 value: the salt, followed by the AES-256-CBC ciphertext.
+    /// </summary>
+    /// <remarks>
+    /// Organizations deployed configuration plugins in this format, so AI Studio reads it for
+    /// good, as decided on 2026-10-17. This is no compatibility shim with a removal date.
+    /// </remarks>
+    /// <returns>The decrypted bytes, or null when the payload is too short.</returns>
+    private byte[]? DecryptV1(byte[] encryptedBytes)
+    {
+        if (encryptedBytes.Length < SALT_LENGTH + 1)
+        {
+            this.logger.LogWarning("Cannot decrypt: Encrypted data is too short.");
+            return null;
+        }
+
+        // Extract salt and encrypted content:
+        var salt = encryptedBytes[..SALT_LENGTH];
+        var cipherText = encryptedBytes[SALT_LENGTH..];
+
+        // Decrypt using AES-256-CBC:
+        using var aes = this.CreateAesV1(salt);
+        using var decryptor = aes.CreateDecryptor();
+        return decryptor.TransformFinalBlock(cipherText, 0, cipherText.Length);
+    }
+
+    /// <summary>
+    /// Creates the AES-256-CBC instance for a v1 value, with key and IV derived from the secret
+    /// and the salt of that value.
+    /// </summary>
+    private Aes CreateAesV1(byte[] salt)
+    {
+        // Derive key and IV using PBKDF2:
+        using var keyDerivation = new Rfc2898DeriveBytes(this.secretKey!, salt, V1_ITERATIONS, HashAlgorithmName.SHA512);
+        var aes = Aes.Create();
+        aes.Key = keyDerivation.GetBytes(32); // AES-256
+        aes.IV = keyDerivation.GetBytes(16);  // AES block size
+        aes.Mode = CipherMode.CBC;
+        aes.Padding = PaddingMode.PKCS7;
+        return aes;
+    }
+
+    /// <summary>
+    /// Encrypts into a v2 value: the salt, the nonce, the AES-256-GCM ciphertext, and its tag.
+    /// </summary>
+    private string EncryptV2(byte[] plaintextBytes)
+    {
+        // The random salt gives every value a key of its own; a random nonce on top costs nothing:
+        var salt = RandomNumberGenerator.GetBytes(SALT_LENGTH);
+        var nonce = RandomNumberGenerator.GetBytes(V2_NONCE_LENGTH);
+        var cipherText = new byte[plaintextBytes.Length];
+        var tag = new byte[V2_TAG_LENGTH];
+
+        using var aes = new AesGcm(this.DeriveKeyV2(salt), V2_TAG_LENGTH);
+        aes.Encrypt(nonce, plaintextBytes, cipherText, tag, V2_ASSOCIATED_DATA);
+
+        byte[] combined = [..salt, ..nonce, ..cipherText, ..tag];
+        return PREFIX_V2 + Convert.ToBase64String(combined);
+    }
+
+    /// <summary>
+    /// Decrypts the payload of a v2 value: the salt, the nonce, the AES-256-GCM ciphertext, and its tag.
+    /// </summary>
+    /// <remarks>
+    /// Throws an AuthenticationTagMismatchException, which is a CryptographicException, when the
+    /// tag does not match: for a wrong secret as well as for a changed value.
+    /// </remarks>
+    /// <returns>The decrypted bytes, or null when the payload is too short.</returns>
+    private byte[]? DecryptV2(byte[] encryptedBytes)
+    {
+        if (encryptedBytes.Length < SALT_LENGTH + V2_NONCE_LENGTH + V2_TAG_LENGTH)
+        {
+            this.logger.LogWarning("Cannot decrypt: Encrypted data is too short.");
+            return null;
+        }
+
+        var salt = encryptedBytes[..SALT_LENGTH];
+        var nonce = encryptedBytes[SALT_LENGTH..(SALT_LENGTH + V2_NONCE_LENGTH)];
+        var cipherText = encryptedBytes[(SALT_LENGTH + V2_NONCE_LENGTH)..^V2_TAG_LENGTH];
+        var tag = encryptedBytes[^V2_TAG_LENGTH..];
+
+        using var aes = new AesGcm(this.DeriveKeyV2(salt), V2_TAG_LENGTH);
+        var decryptedBytes = new byte[cipherText.Length];
+        aes.Decrypt(nonce, cipherText, tag, decryptedBytes, V2_ASSOCIATED_DATA);
+        return decryptedBytes;
+    }
+
+    /// <summary>
+    /// Derives the AES-256 key of a v2 value from the secret and the salt of that value.
+    /// </summary>
+    /// <remarks>
+    /// Unlike a password, the secret is meant to be 256 random bits, as GenerateSecret makes it.
+    /// Stretching it, as PBKDF2 does for v1 values, adds nothing, so HKDF suffices.
+    /// </remarks>
+    private byte[] DeriveKeyV2(byte[] salt) => HKDF.DeriveKey(HashAlgorithmName.SHA256, this.secretKey!, 32, salt, V2_KEY_INFO);
 }

app/MindWork AI Studio/Tools/EnterpriseEncryptionFormat.cs

@@ -0,0 +1,19 @@
+namespace AIStudio.Tools;
+
+/// <summary>
+/// The formats in which AI Studio encrypts the secrets of enterprise configuration plugins.
+/// </summary>
+public enum EnterpriseEncryptionFormat
+{
+    /// <summary>
+    /// "ENC:v1:", which every version of AI Studio reads. It is not authenticated, so a wrong
+    /// encryption secret is not always detected.
+    /// </summary>
+    V1,
+
+    /// <summary>
+    /// "ENC:v2:", which is authenticated: AI Studio refuses every value encrypted with another
+    /// secret or changed afterward. Versions before v26.10.1 cannot read it.
+    /// </summary>
+    V2,
+}

app/MindWork AI Studio/Tools/PluginSystem/PluginConfiguration.cs

@@ -305,6 +305,9 @@ public sealed class PluginConfiguration(bool isInternal, LuaState state, PluginT
         // Config: show administration settings?
         ManagedConfiguration.TryProcessConfiguration(x => x.App, x => x.ShowAdminSettings, this.Id, settingsTable, dryRun);
 
+        // Config: in which format do exports encrypt secrets?
+        ManagedConfiguration.TryProcessConfiguration(x => x.App, x => x.EnterpriseEncryptionExportFormat, this.Id, settingsTable, dryRun);
+
         // Config: add a disclosure to copied and exported AI-generated content?
         ManagedConfiguration.TryProcessConfiguration(x => x.App, x => x.AddAIGeneratedContentDisclosure, this.Id, settingsTable, dryRun);
         

app/MindWork AI Studio/Tools/ToolCallingSystem/ToolSettingsService.Export.cs

@@ -73,7 +73,7 @@ public sealed partial class ToolSettingsService
                 continue;
 
             var values = await this.GetSettingsAsync(tool.Definition);
-            var issue = CollectSettings(tool.Definition, areasOfTool, values, options, PluginFactory.EnterpriseEncryption, lockedValues, defaultValues);
+            var issue = CollectSettings(tool.Definition, areasOfTool, values, options, PluginFactory.EnterpriseEncryption, settingsManager.ConfigurationData.App.EnterpriseEncryptionExportFormat, lockedValues, defaultValues);
             if (issue is not null)
                 return new(ErrorMessage: issue);
         }
@@ -98,7 +98,7 @@ public sealed partial class ToolSettingsService
     /// Adds the selected settings of one tool to the values to export, by their managed key.
     /// </summary>
     /// <returns>Why the export failed, or null when it may go on.</returns>
-    private static string? CollectSettings(ToolDefinition definition, IEnumerable<ExportableSettings> selectedAreas, IReadOnlyDictionary<string, string> values, ToolSettingsExportOptions options, EnterpriseEncryption? encryption, Dictionary<string, string> lockedValues, Dictionary<string, string> defaultValues)
+    private static string? CollectSettings(ToolDefinition definition, IEnumerable<ExportableSettings> selectedAreas, IReadOnlyDictionary<string, string> values, ToolSettingsExportOptions options, EnterpriseEncryption? encryption, EnterpriseEncryptionFormat encryptionFormat, Dictionary<string, string> lockedValues, Dictionary<string, string> defaultValues)
     {
         foreach (var fieldName in GetSelectedFieldNames(definition, selectedAreas))
         {
@@ -114,7 +114,7 @@ public sealed partial class ToolSettingsService
                 if (encryption?.IsAvailable is not true)
                     return TB("Cannot export encrypted tool secrets: No enterprise encryption secret is configured.");
 
-                if (!encryption.TryEncrypt(value, out var encrypted))
+                if (!encryption.TryEncrypt(value, encryptionFormat, out var encrypted))
                     return TB("The tool secrets could not be encrypted. Nothing was exported.");
 
                 lockedValues[key] = encrypted;

app/MindWork AI Studio/Tools/ToolCallingSystem/ToolSettingsService.cs

@@ -182,7 +182,7 @@ public sealed partial class ToolSettingsService(SettingsManager settingsManager,
 
         if (!EnterpriseEncryption.IsEncrypted(encryptedSecret))
         {
-            logger.LogWarning("The managed tool setting '{ManagedKey}' holds a plaintext secret. Only encrypted secrets, starting with 'ENC:v1:', are supported.", managedKey);
+            logger.LogWarning("The managed tool setting '{ManagedKey}' holds a plaintext secret. Only encrypted secrets, starting with 'ENC:', are supported.", managedKey);
             return false;
         }