Merge branch 'mlin/PR/ExposeUnsealedContent'

We need to plumb through groupId. Desktop needs this to properly handle
resend responses.

SignalMetadataKit.podspec

@@ -39,15 +39,12 @@ A Swift & Objective-C library used by other Signal libraries.
 
   s.resources = ["SignalMetadataKit/Resources/Certificates/*"]
 
-  s.dependency 'AxolotlKit'
   s.dependency 'CocoaLumberjack'
   s.dependency 'Curve25519Kit'
-  s.dependency 'HKDFKit'
+  s.dependency 'SignalClient'
   s.dependency 'SignalCoreKit'
   s.dependency 'SwiftProtobuf'
 
-  s.dependency 'SignalClient'
-
   s.test_spec 'Tests' do |test_spec|
     test_spec.source_files = 'SignalMetadataKitTests/src/**/*.{h,m,swift}'
   end

SignalMetadataKit/src/SMKCertificateValidator.swift

@@ -1,5 +1,5 @@
 //
-//  Copyright (c) 2020 Open Whisper Systems. All rights reserved.
+//  Copyright (c) 2021 Open Whisper Systems. All rights reserved.
 //
 
 import Foundation
@@ -11,10 +11,7 @@ public enum SMKCertificateError: Error {
     case invalidCertificate(description: String)
 }
 
-@objc(SMKCertificateValidator)
-public protocol SMKCertificateValidatorObjC {}
-
-public protocol SMKCertificateValidator: SMKCertificateValidatorObjC {
+public protocol SMKCertificateValidator {
     func throwswrapped_validate(senderCertificate: SenderCertificate, validationTime: UInt64) throws
     func throwswrapped_validate(serverCertificate: ServerCertificate) throws
 }
@@ -53,9 +50,9 @@ public protocol SMKCertificateValidator: SMKCertificateValidatorObjC {
 //    }
         guard try serverCertificate.publicKey.verifySignature(message: senderCertificate.certificateBytes,
                                                               signature: senderCertificate.signatureBytes) else {
-            OWSLog.error("Sender certificate signature verification failed.")
+            Logger.error("Sender certificate signature verification failed.")
             let error = SMKCertificateError.invalidCertificate(description: "Sender certificate signature verification failed.")
-            OWSLog.error("\(error)")
+            Logger.error("\(error)")
             throw error
         }
 
@@ -64,7 +61,7 @@ public protocol SMKCertificateValidator: SMKCertificateValidatorObjC {
 //    }
         guard validationTime <= senderCertificate.expiration else {
             let error = SMKCertificateError.invalidCertificate(description: "Certficate is expired.")
-            OWSLog.error("\(error)")
+            Logger.error("\(error)")
             throw error
         }
 
@@ -82,7 +79,7 @@ public protocol SMKCertificateValidator: SMKCertificateValidatorObjC {
         guard try trustRoot.key.verifySignature(message: serverCertificate.certificateBytes,
                                                 signature: serverCertificate.signatureBytes) else {
             let error = SMKCertificateError.invalidCertificate(description: "Server certificate signature verification failed.")
-            OWSLog.error("\(error)")
+            Logger.error("\(error)")
             throw error
         }
 
@@ -91,7 +88,7 @@ public protocol SMKCertificateValidator: SMKCertificateValidatorObjC {
         // }
         guard !SMKCertificateDefaultValidator.kRevokedCertificateIds.contains(serverCertificate.keyId) else {
             let error = SMKCertificateError.invalidCertificate(description: "Revoked certificate.")
-            OWSLog.error("\(error)")
+            Logger.error("\(error)")
             throw error
         }
 

SignalMetadataKit/src/SMKSecretSessionCipher.swift

@@ -3,47 +3,28 @@
 //
 
 import Foundation
-import AxolotlKit
 import Curve25519Kit
+import SignalCoreKit
 import SignalClient
 
-@objc
-public class SecretSessionKnownSenderError: NSObject, CustomNSError {
-    @objc
-    public static let kSenderE164Key = "kSenderE164Key"
-
-    @objc
-    public static let kSenderUuidKey = "kSenderUuidKey"
-
-    @objc
-    public static let kSenderDeviceIdKey = "kSenderDeviceIdKey"
-
+public struct SecretSessionKnownSenderError: Error {
     public let senderAddress: SMKAddress
     public let senderDeviceId: UInt32
+    public let cipherType: CiphertextMessage.MessageType
+    public let groupId: Data?
+    public let unsealedContent: Data
+    public let contentHint: UnidentifiedSenderMessageContent.ContentHint
     public let underlyingError: Error
 
-    init(senderAddress: SMKAddress, senderDeviceId: UInt32, underlyingError: Error) {
-        self.senderAddress = senderAddress
-        self.senderDeviceId = senderDeviceId
+    init(messageContent: UnidentifiedSenderMessageContent, underlyingError: Error) {
+        self.senderAddress = SMKAddress(messageContent.senderCertificate.sender)
+        self.senderDeviceId = messageContent.senderCertificate.sender.deviceId
+        self.cipherType = messageContent.messageType
+        self.groupId = messageContent.groupId.map { Data($0) }
+        self.unsealedContent = Data(messageContent.contents)
+        self.contentHint = messageContent.contentHint
         self.underlyingError = underlyingError
     }
-
-    public var errorUserInfo: [String: Any] {
-        var info: [String: Any] = [
-            type(of: self).kSenderDeviceIdKey: self.senderDeviceId,
-            NSUnderlyingErrorKey: (underlyingError as NSError)
-        ]
-
-        if let e164 = senderAddress.e164 {
-            info[type(of: self).kSenderE164Key] = e164
-        }
-
-        if let uuid = senderAddress.uuid {
-            info[type(of: self).kSenderUuidKey] = uuid
-        }
-
-        return info
-    }
 }
 
 @objc
@@ -97,6 +78,8 @@ private class SMKStaticKeys: NSObject {
 @objc public enum SMKMessageType: Int {
     case whisper
     case prekey
+    case senderKey
+    case plaintext
 }
 
 @objc
@@ -152,6 +135,10 @@ fileprivate extension SMKMessageType {
             self = .whisper
         case .preKey:
             self = .prekey
+        case .senderKey:
+            self = .senderKey
+        case .plaintext:
+            self = .plaintext
         default:
             fatalError("not ready for other kinds of messages yet")
         }
@@ -164,74 +151,113 @@ fileprivate extension SMKMessageType {
 
     private let kSMKSecretSessionCipherMacLength: UInt = 10
 
-    private let sessionStore: SignalClient.SessionStore
-    private let preKeyStore: SignalClient.PreKeyStore
-    private let signedPreKeyStore: SignalClient.SignedPreKeyStore
-    private let identityStore: SignalClient.IdentityKeyStore
+    private let sessionStore: SessionStore
+    private let preKeyStore: PreKeyStore
+    private let signedPreKeyStore: SignedPreKeyStore
+    private let identityStore: IdentityKeyStore
+    private let senderKeyStore: SenderKeyStore
 
     // public SecretSessionCipher(SignalProtocolStore signalProtocolStore) {
-    public init(sessionStore: SignalClient.SessionStore,
-                preKeyStore: SignalClient.PreKeyStore,
-                signedPreKeyStore: SignalClient.SignedPreKeyStore,
-                identityStore: SignalClient.IdentityKeyStore) throws {
+    public init(sessionStore: SessionStore,
+                preKeyStore: PreKeyStore,
+                signedPreKeyStore: SignedPreKeyStore,
+                identityStore: IdentityKeyStore,
+                senderKeyStore: SenderKeyStore) throws {
 
         self.sessionStore = sessionStore
         self.preKeyStore = preKeyStore
         self.signedPreKeyStore = signedPreKeyStore
         self.identityStore = identityStore
-    }
-
-    @objc(initWithSessionStore:preKeyStore:signedPreKeyStore:identityStore:error:)
-    public convenience init(transitionalSessionStore sessionStore: AxolotlKit.SessionStore,
-                            preKeyStore: AxolotlKit.PreKeyStore,
-                            signedPreKeyStore: AxolotlKit.SignedPreKeyStore,
-                            identityStore: AxolotlKit.IdentityKeyStore) throws {
-        try self.init(
-            sessionStore: sessionStore as! SignalClient.SessionStore,
-            preKeyStore: preKeyStore as! SignalClient.PreKeyStore,
-            signedPreKeyStore: signedPreKeyStore as! SignalClient.SignedPreKeyStore,
-            identityStore: identityStore as! SignalClient.IdentityKeyStore)
+        self.senderKeyStore = senderKeyStore
     }
 
     // MARK: - Public
 
-    // public byte[] encrypt(SignalProtocolAddress destinationAddress, SenderCertificate senderCertificate, byte[] paddedPlaintext)
-    public func throwswrapped_encryptMessage(recipient: SMKAddress,
-                                             deviceId: Int32,
-                                             paddedPlaintext: Data,
-                                             senderCertificate: SenderCertificate,
-                                             protocolContext: SPKProtocolWriteContext?) throws -> Data {
+    public func encryptMessage(
+        recipient: SMKAddress,
+        deviceId: Int32,
+        paddedPlaintext: Data,
+        contentHint: UnidentifiedSenderMessageContent.ContentHint,
+        groupId: Data?,
+        senderCertificate: SenderCertificate,
+        protocolContext: StoreContext
+    ) throws -> Data {
+
         guard deviceId > 0 else {
             throw SMKError.assertionError(description: "\(logTag) invalid deviceId")
         }
-
-        // CiphertextMessage message = new SessionCipher(signalProtocolStore, destinationAddress).encrypt(paddedPlaintext);
         let recipientAddress = try ProtocolAddress(from: recipient, deviceId: UInt32(bitPattern: deviceId))
-        // Allow nil contexts for testing.
-        return Data(try sealedSenderEncrypt(message: paddedPlaintext,
-                                            for: recipientAddress,
-                                            from: senderCertificate,
-                                            sessionStore: sessionStore,
-                                            identityStore: identityStore,
-                                            context: (protocolContext as! StoreContext?) ?? NullContext()))
+
+
+        let ciphertextMessage = try signalEncrypt(
+            message: paddedPlaintext,
+            for: recipientAddress,
+            sessionStore: sessionStore,
+            identityStore: identityStore,
+            context: protocolContext)
+
+        let usmc = try UnidentifiedSenderMessageContent(
+            ciphertextMessage,
+            from: senderCertificate,
+            contentHint: contentHint,
+            groupId: groupId ?? Data())
+
+        let outerBytes = try sealedSenderEncrypt(
+            usmc,
+            for: recipientAddress,
+            identityStore: identityStore,
+            context: protocolContext)
+
+        return Data(outerBytes)
+    }
+
+    public func groupEncryptMessage(recipients: [ProtocolAddress],
+                                    paddedPlaintext: Data,
+                                    senderCertificate: SenderCertificate,
+                                    groupId: Data,
+                                    distributionId: UUID,
+                                    contentHint: UnidentifiedSenderMessageContent.ContentHint = .default,
+                                    protocolContext: StoreContext?) throws -> Data {
+
+        let senderAddress = try ProtocolAddress(from: senderCertificate.sender)
+        let ciphertext = try groupEncrypt(
+            paddedPlaintext,
+            from: senderAddress,
+            distributionId: distributionId,
+            store: senderKeyStore,
+            context: protocolContext ?? NullContext())
+
+        let udMessageContent = try UnidentifiedSenderMessageContent(
+            ciphertext,
+            from: senderCertificate,
+            contentHint: contentHint,
+            groupId: groupId)
+
+        let multiRecipientMessage = try sealedSenderMultiRecipientEncrypt(
+            udMessageContent,
+            for: recipients,
+            identityStore: identityStore,
+            sessionStore: sessionStore,
+            context: protocolContext ?? NullContext())
+
+        return Data(multiRecipientMessage)
     }
 
     // public Pair<SignalProtocolAddress, byte[]> decrypt(CertificateValidator validator, byte[] ciphertext, long timestamp)
     //    throws InvalidMetadataMessageException, InvalidMetadataVersionException, ProtocolInvalidMessageException, ProtocolInvalidKeyException, ProtocolNoSessionException, ProtocolLegacyMessageException, ProtocolInvalidVersionException, ProtocolDuplicateMessageException, ProtocolInvalidKeyIdException, ProtocolUntrustedIdentityException
-    @objc
-    public func throwswrapped_decryptMessage(certificateValidator: SMKCertificateValidatorObjC,
+    public func throwswrapped_decryptMessage(certificateValidator: SMKCertificateValidator,
                                              cipherTextData: Data,
                                              timestamp: UInt64,
                                              localE164: String?,
                                              localUuid: UUID?,
                                              localDeviceId: Int32,
-                                             protocolContext: SPKProtocolWriteContext?) throws -> SMKDecryptResult {
+                                             protocolContext: StoreContext?) throws -> SMKDecryptResult {
         guard timestamp > 0 else {
             throw SMKError.assertionError(description: "\(logTag) invalid timestamp")
         }
 
         // Allow nil contexts for testing.
-        let context = (protocolContext as! StoreContext?) ?? NullContext()
+        let context = protocolContext ?? NullContext()
         let messageContent = try UnidentifiedSenderMessageContent(message: cipherTextData,
                                                                   identityStore: self.identityStore,
                                                                   context: context)
@@ -241,13 +267,12 @@ fileprivate extension SMKMessageType {
 
         guard !SMKAddress(senderAddress).matches(localAddress) ||
                 Int32(bitPattern: senderAddress.deviceId) != localDeviceId else {
-            OWSLog.info("Discarding self-sent message")
+            Logger.info("Discarding self-sent message")
             throw SMKSecretSessionCipherError.selfSentMessage
         }
 
         do {
             // validator.validate(content.getSenderCertificate(), timestamp);
-            let certificateValidator = certificateValidator as! SMKCertificateValidator
             try certificateValidator.throwswrapped_validate(
                 senderCertificate: messageContent.senderCertificate,
                 validationTime: timestamp)
@@ -268,8 +293,7 @@ fileprivate extension SMKMessageType {
                                     paddedPayload: Data(paddedMessagePlaintext),
                                     messageType: SMKMessageType(messageContent.messageType))
         } catch {
-            throw SecretSessionKnownSenderError(senderAddress: SMKAddress(senderAddress),
-                                                senderDeviceId: senderAddress.deviceId,
+            throw SecretSessionKnownSenderError(messageContent: messageContent,
                                                 underlyingError: error)
         }
     }
@@ -317,6 +341,15 @@ fileprivate extension SMKMessageType {
                 preKeyStore: preKeyStore,
                 signedPreKeyStore: signedPreKeyStore,
                 context: context)
+        case .senderKey:
+            plaintextData = try groupDecrypt(
+                messageContent.contents,
+                from: ProtocolAddress(from: sender),
+                store: senderKeyStore,
+                context: context)
+        case .plaintext:
+            let plaintextMessage = try PlaintextContent(bytes: messageContent.contents)
+            plaintextData = plaintextMessage.body
         case let unknownType:
             throw SMKError.assertionError(
                 description: "\(logTag) Not prepared to handle this message type: \(unknownType.rawValue)")
@@ -324,3 +357,28 @@ fileprivate extension SMKMessageType {
         return Data(plaintextData)
     }
 }
+
+// MARK: - Internal for testing
+
+extension SMKSecretSessionCipher {
+
+    // Only allow nil contexts for testing
+    func encryptMessage(
+        recipient: SMKAddress,
+        deviceId: Int32,
+        paddedPlaintext: Data,
+        contentHint: UnidentifiedSenderMessageContent.ContentHint = .default,
+        groupId: Data? = nil,
+        senderCertificate: SenderCertificate,
+        protocolContext: StoreContext? = nil
+    ) throws -> Data {
+        try encryptMessage(
+            recipient: recipient,
+            deviceId: deviceId,
+            paddedPlaintext: paddedPlaintext,
+            contentHint: contentHint,
+            groupId: groupId,
+            senderCertificate: senderCertificate,
+            protocolContext: protocolContext ?? NullContext())
+    }
+}

SignalMetadataKit/src/SMKUDAccessKey.swift

@@ -42,10 +42,30 @@ public class SMKUDAccessKey: NSObject {
         self.keyData = Randomness.generateRandomBytes(Int32(SMKUDAccessKey.kUDAccessKeyLength))
     }
 
+    private init(keyData: Data) {
+        self.keyData = keyData
+    }
+
+    /// Used to compose multiple Unidentified-Access-Keys for the multiRecipient endpoint
+    public static func ^(lhs: SMKUDAccessKey, rhs: SMKUDAccessKey) -> SMKUDAccessKey {
+        owsAssert(lhs.keyData.count == SMKUDAccessKey.kUDAccessKeyLength)
+        owsAssert(rhs.keyData.count == SMKUDAccessKey.kUDAccessKeyLength)
+
+        let xoredBytes = zip(lhs.keyData, rhs.keyData).map(^)
+        return .init(keyData: Data(xoredBytes))
+    }
+
     // MARK: 
     
     override public func isEqual(_ object: Any?) -> Bool {
         guard let other = object as? SMKUDAccessKey else { return false }
         return self.keyData == other.keyData
     }
+
+    // Unrestricted UD recipients should have a zeroed access key sent to the multi-recipient endpoint
+    // For a collection of mixed recipients, a zeroed key will have no effect composing keys with xor
+    // For a collection of only unrestricted UD recipients, the server expects a zero access key
+    public static var zeroedKey: SMKUDAccessKey {
+        .init(keyData: Data(repeating: 0, count: kUDAccessKeyLength))
+    }
 }

SignalMetadataKitTests/src/SMKMiscTest.swift

@@ -3,7 +3,7 @@
 //
 
 import XCTest
-import SignalMetadataKit
+@testable import SignalMetadataKit
 import SignalCoreKit
 import Curve25519Kit
 import SignalClient
@@ -51,11 +51,10 @@ class SMKTest: XCTestCase {
         let plaintext = Randomness.generateRandomBytes(200)
         let paddedPlaintext = (plaintext as NSData).paddedMessageBody()
         let senderCertificate = try! SenderCertificate(buildSenderCertificateProto(senderClient: aliceMockClient).serializedData())
-        let encryptedMessage = try! aliceToBobCipher.throwswrapped_encryptMessage(recipient: bobMockClient.address,
-                                                                                  deviceId: bobMockClient.deviceId,
-                                                                                  paddedPlaintext: paddedPlaintext,
-                                                                                  senderCertificate: senderCertificate,
-                                                                                  protocolContext: nil)
+        let encryptedMessage = try! aliceToBobCipher.encryptMessage(recipient: bobMockClient.address,
+                                                                    deviceId: bobMockClient.deviceId,
+                                                                    paddedPlaintext: paddedPlaintext,
+                                                                    senderCertificate: senderCertificate)
 
         let messageTimestamp = NSDate.ows_millisecondTimeStamp()
 

SignalMetadataKitTests/src/SMKSecretSessionCipherTest.swift

@@ -3,9 +3,10 @@
 //
 
 import XCTest
-import SignalMetadataKit
-import SignalClient
+@testable import SignalMetadataKit
+@testable import SignalClient
 import Curve25519Kit
+import SignalCoreKit
 
 // https://github.com/signalapp/libsignal-metadata-java/blob/master/tests/src/test/java/org/signal/libsignal/metadata/SecretSessionCipherTest.java
 // public class SecretSessionCipherTest extends TestCase {
@@ -39,11 +40,10 @@ class SMKSecretSessionCipherTest: XCTestCase {
         // senderCertificate, "smert za smert".getBytes());
         // NOTE: The java tests don't bother padding the plaintext.
         let alicePlaintext = "smert za smert".data(using: String.Encoding.utf8)!
-        let ciphertext = try! aliceCipher.throwswrapped_encryptMessage(recipient: bobMockClient.address,
-                                                                       deviceId: bobMockClient.deviceId,
-                                                                       paddedPlaintext: alicePlaintext,
-                                                                       senderCertificate: senderCertificate,
-                                                                       protocolContext: nil)
+        let ciphertext = try! aliceCipher.encryptMessage(recipient: bobMockClient.address,
+                                                         deviceId: bobMockClient.deviceId,
+                                                         paddedPlaintext: alicePlaintext,
+                                                         senderCertificate: senderCertificate)
 
         // SealedSessionCipher bobCipher = new SealedSessionCipher(bobStore, new SignalProtocolAddress("+14152222222", 1));
         let bobCipher: SMKSecretSessionCipher = try! bobMockClient.createSecretSessionCipher()
@@ -95,11 +95,14 @@ class SMKSecretSessionCipherTest: XCTestCase {
         // senderCertificate, "и вот я".getBytes());
         // NOTE: The java tests don't bother padding the plaintext.
         let alicePlaintext = "и вот я".data(using: String.Encoding.utf8)!
-        let ciphertext = try! aliceCipher.throwswrapped_encryptMessage(recipient: bobMockClient.address,
-                                                                       deviceId: bobMockClient.deviceId,
-                                                                       paddedPlaintext: alicePlaintext,
-                                                                       senderCertificate: senderCertificate,
-                                                                       protocolContext: nil)
+        let aliceGroupId = Randomness.generateRandomBytes(6)
+        let aliceContentHint = UnidentifiedSenderMessageContent.ContentHint.implicit
+        let ciphertext = try! aliceCipher.encryptMessage(recipient: bobMockClient.address,
+                                                         deviceId: bobMockClient.deviceId,
+                                                         paddedPlaintext: alicePlaintext,
+                                                         contentHint: aliceContentHint,
+                                                         groupId: aliceGroupId,
+                                                         senderCertificate: senderCertificate)
 
         // SecretSessionCipher bobCipher = new SecretSessionCipher(bobStore);
         let bobCipher: SMKSecretSessionCipher = try! bobMockClient.createSecretSessionCipher()
@@ -123,6 +126,16 @@ class SMKSecretSessionCipherTest: XCTestCase {
         } catch let knownSenderError as SecretSessionKnownSenderError {
             // Decryption is expected to fail.
             XCTAssert(knownSenderError.underlyingError is SMKCertificateError )
+            XCTAssertEqual(knownSenderError.contentHint, aliceContentHint)
+            XCTAssertEqual(knownSenderError.groupId, aliceGroupId)
+            XCTAssertNoThrow(
+                try DecryptionErrorMessage(
+                    originalMessageBytes: knownSenderError.unsealedContent,
+                    type: knownSenderError.cipherType,
+                    timestamp: 31335,
+                    originalSenderDeviceId: knownSenderError.senderDeviceId
+                )
+            )
         } catch {
             XCTFail("Unexpected error: \(error)")
         }
@@ -156,11 +169,15 @@ class SMKSecretSessionCipherTest: XCTestCase {
         //     senderCertificate, "и вот я".getBytes());
         // NOTE: The java tests don't bother padding the plaintext.
         let alicePlaintext = "и вот я".data(using: String.Encoding.utf8)!
-        let ciphertext = try! aliceCipher.throwswrapped_encryptMessage(recipient: bobMockClient.address,
-                                                                       deviceId: bobMockClient.deviceId,
-                                                                       paddedPlaintext: alicePlaintext,
-                                                                       senderCertificate: senderCertificate,
-                                                                       protocolContext: nil)
+        let aliceGroupId = Randomness.generateRandomBytes(6)
+        let aliceContentHint = UnidentifiedSenderMessageContent.ContentHint.resendable
+
+        let ciphertext = try! aliceCipher.encryptMessage(recipient: bobMockClient.address,
+                                                         deviceId: bobMockClient.deviceId,
+                                                         paddedPlaintext: alicePlaintext,
+                                                         contentHint: aliceContentHint,
+                                                         groupId: aliceGroupId,
+                                                         senderCertificate: senderCertificate)
 
         // SecretSessionCipher bobCipher = new SecretSessionCipher(bobStore);
         let bobCipher: SMKSecretSessionCipher = try! bobMockClient.createSecretSessionCipher()
@@ -184,6 +201,16 @@ class SMKSecretSessionCipherTest: XCTestCase {
         } catch let knownSenderError as SecretSessionKnownSenderError {
             // Decryption is expected to fail.
             XCTAssert(knownSenderError.underlyingError is SMKCertificateError )
+            XCTAssertEqual(knownSenderError.contentHint, aliceContentHint)
+            XCTAssertEqual(knownSenderError.groupId, aliceGroupId)
+            XCTAssertNoThrow(
+                try DecryptionErrorMessage(
+                    originalMessageBytes: knownSenderError.unsealedContent,
+                    type: knownSenderError.cipherType,
+                    timestamp: 31338,
+                    originalSenderDeviceId: knownSenderError.senderDeviceId
+                )
+            )
         } catch {
             XCTFail("Unexpected error: \(error)")
         }
@@ -218,11 +245,10 @@ class SMKSecretSessionCipherTest: XCTestCase {
         //    senderCertificate, "smert za smert".getBytes());
         // NOTE: The java tests don't bother padding the plaintext.
         let alicePlaintext = "smert za smert".data(using: String.Encoding.utf8)!
-        let ciphertext = try! aliceCipher.throwswrapped_encryptMessage(recipient: bobMockClient.address,
-                                                                       deviceId: bobMockClient.deviceId,
-                                                                       paddedPlaintext: alicePlaintext,
-                                                                       senderCertificate: senderCertificate,
-                                                                       protocolContext: nil)
+        let ciphertext = try! aliceCipher.encryptMessage(recipient: bobMockClient.address,
+                                                         deviceId: bobMockClient.deviceId,
+                                                         paddedPlaintext: alicePlaintext,
+                                                         senderCertificate: senderCertificate)
 
         // SecretSessionCipher bobCipher = new SecretSessionCipher(bobStore);
         let bobCipher: SMKSecretSessionCipher = try! bobMockClient.createSecretSessionCipher()
@@ -252,6 +278,148 @@ class SMKSecretSessionCipherTest: XCTestCase {
         }
     }
 
+    func testGroupEncryptDecrypt_Success() {
+        // Setup: Initialize sessions and sender certificate
+        let aliceMockClient = MockClient(address: aliceAddress, deviceId: 1, registrationId: 1234)
+        let bobMockClient = MockClient(address: bobAddress, deviceId: 1, registrationId: 1235)
+        initializeSessions(aliceMockClient: aliceMockClient, bobMockClient: bobMockClient)
+
+        let trustRoot = IdentityKeyPair.generate()
+        let senderCertificate = createCertificateFor(
+            trustRoot: trustRoot,
+            senderAddress: aliceMockClient.address,
+            senderDeviceId: UInt32(aliceMockClient.deviceId),
+            identityKey: aliceMockClient.identityKeyPair.publicKey,
+            expirationTimestamp: 31337)
+
+        // Setup: Distribute alice's sender key to bob's key store
+        let distributionId = UUID()
+        let aliceSenderKeyMessage = try! SenderKeyDistributionMessage(
+            from: aliceMockClient.protocolAddress,
+            distributionId: distributionId,
+            store: aliceMockClient.senderKeyStore,
+            context: NullContext())
+
+        try! processSenderKeyDistributionMessage(
+            aliceSenderKeyMessage,
+            from: aliceMockClient.protocolAddress,
+            store: bobMockClient.senderKeyStore,
+            context: NullContext())
+
+        // Test: Alice encrypt's a message using `groupEncryptMessage`
+        let aliceCipher = try! aliceMockClient.createSecretSessionCipher()
+        let alicePlaintext = "beltalowda".data(using: String.Encoding.utf8)!
+        let aliceCiphertext = try! aliceCipher.groupEncryptMessage(
+            recipients: [bobMockClient.protocolAddress],
+            paddedPlaintext: alicePlaintext,
+            senderCertificate: senderCertificate,
+            groupId: Data(),
+            distributionId: distributionId,
+            contentHint: .implicit,
+            protocolContext: nil).map { $0 }
+
+        // This splits out irrelevant per-recipient data from the shared sender key message
+        // This is only necessary in tests. The server would usually handle this.
+        let singleRecipientCiphertext = try! sealedSenderMultiRecipientMessageForSingleRecipient(aliceCiphertext)
+
+        // Test: Bob decrypts the ciphertext
+        let bobCipher = try! bobMockClient.createSecretSessionCipher()
+        let bobValidator = SMKCertificateDefaultValidator(trustRoot: ECPublicKey(trustRoot.publicKey))
+        let bobPlaintext = try! bobCipher.throwswrapped_decryptMessage(
+            certificateValidator: bobValidator,
+            cipherTextData: Data(singleRecipientCiphertext),
+            timestamp: 31335,
+            localE164: bobMockClient.recipientE164,
+            localUuid: bobMockClient.recipientUuid,
+            localDeviceId: bobMockClient.deviceId,
+            protocolContext: nil)
+
+        // Verify
+        XCTAssertEqual(String(data: bobPlaintext.paddedPayload, encoding: .utf8), "beltalowda")
+        XCTAssertEqual(bobPlaintext.senderAddress, aliceMockClient.address)
+        XCTAssertEqual(bobPlaintext.senderDeviceId, Int(aliceMockClient.deviceId))
+        XCTAssertEqual(bobPlaintext.messageType, .senderKey)
+    }
+
+    func testGroupEncryptDecrypt_Failure() {
+        // Setup: Initialize sessions and sender certificate
+        let aliceMockClient = MockClient(address: aliceAddress, deviceId: 1, registrationId: 1234)
+        let bobMockClient = MockClient(address: bobAddress, deviceId: 1, registrationId: 1235)
+        initializeSessions(aliceMockClient: aliceMockClient, bobMockClient: bobMockClient)
+
+        let trustRoot = IdentityKeyPair.generate()
+        let senderCertificate = createCertificateFor(
+            trustRoot: trustRoot,
+            senderAddress: aliceMockClient.address,
+            senderDeviceId: UInt32(aliceMockClient.deviceId),
+            identityKey: aliceMockClient.identityKeyPair.publicKey,
+            expirationTimestamp: 31337)
+
+        // Setup: Alice creates a sender key
+        // Test: Bob intentionally does not process Alice's SKDM to simulate an unsent key
+        let distributionId = UUID()
+        let _ = try! SenderKeyDistributionMessage(
+            from: aliceMockClient.protocolAddress,
+            distributionId: distributionId,
+            store: aliceMockClient.senderKeyStore,
+            context: NullContext())
+
+        // Test: Alice encrypt's a message using `groupEncryptMessage`
+        let aliceCipher = try! aliceMockClient.createSecretSessionCipher()
+        let alicePlaintext = "beltalowda".data(using: String.Encoding.utf8)!
+        let aliceCiphertext = try! aliceCipher.groupEncryptMessage(
+            recipients: [bobMockClient.protocolAddress],
+            paddedPlaintext: alicePlaintext,
+            senderCertificate: senderCertificate,
+            groupId: "inyalowda".data(using: String.Encoding.utf8)!,
+            distributionId: distributionId,
+            contentHint: .resendable,
+            protocolContext: nil).map { $0 }
+
+        // This splits out irrelevant per-recipient data from the shared sender key message
+        // This is only necessary in tests. The server would usually handle this.
+        let singleRecipientCiphertext = try! sealedSenderMultiRecipientMessageForSingleRecipient(aliceCiphertext)
+
+        // Test: Bob decrypts the ciphertext
+        let bobCipher = try! bobMockClient.createSecretSessionCipher()
+        let bobValidator = SMKCertificateDefaultValidator(trustRoot: ECPublicKey(trustRoot.publicKey))
+        do {
+            _ = try bobCipher.throwswrapped_decryptMessage(
+                certificateValidator: bobValidator,
+                cipherTextData: Data(singleRecipientCiphertext),
+                timestamp: 31335,
+                localE164: bobMockClient.recipientE164,
+                localUuid: bobMockClient.recipientUuid,
+                localDeviceId: bobMockClient.deviceId,
+                protocolContext: nil)
+            XCTFail("Decryption should have failed.")
+        } catch let knownSenderError as SecretSessionKnownSenderError {
+            // Verify: We need to make sure that the sender, group, and contentHint are preserved
+            // through decryption failures because of missing a missing sender key. This will
+            // help with recovery.
+            XCTAssertEqual(knownSenderError.senderAddress, aliceMockClient.address)
+            XCTAssertEqual(knownSenderError.senderDeviceId, UInt32(aliceMockClient.deviceId))
+            XCTAssertEqual(Data(knownSenderError.groupId!), "inyalowda".data(using: String.Encoding.utf8)!)
+            XCTAssertEqual(knownSenderError.contentHint, .resendable)
+            XCTAssertNoThrow(
+                try DecryptionErrorMessage(
+                    originalMessageBytes: knownSenderError.unsealedContent,
+                    type: knownSenderError.cipherType,
+                    timestamp: 31335,
+                    originalSenderDeviceId: knownSenderError.senderDeviceId
+                )
+            )
+
+            if case SignalError.invalidState(_) = knownSenderError.underlyingError {
+                // Expected
+            } else {
+                XCTFail()
+            }
+        } catch {
+            XCTFail("Unexpected error: \(error)")
+        }
+    }
+
      // MARK: - Utils
 
     // private SenderCertificate createCertificateFor(ECKeyPair trustRoot, String sender, int deviceId, ECPublicKey identityKey, long expires)

SignalMetadataKitTests/src/SMKTestUtils.swift

@@ -32,6 +32,9 @@ class MockClient: NSObject {
     }
 
     let address: SMKAddress
+    var protocolAddress: ProtocolAddress {
+        try! ProtocolAddress(name: address.uuid!.uuidString, deviceId: UInt32(deviceId))
+    }
 
     let deviceId: Int32
     let registrationId: Int32
@@ -42,6 +45,7 @@ class MockClient: NSObject {
     let preKeyStore: InMemorySignalProtocolStore
     let signedPreKeyStore: InMemorySignalProtocolStore
     let identityStore: InMemorySignalProtocolStore
+    let senderKeyStore: InMemorySignalProtocolStore
 
     init(address: SMKAddress, deviceId: Int32, registrationId: Int32) {
         self.address = address
@@ -50,19 +54,21 @@ class MockClient: NSObject {
         self.identityKeyPair = IdentityKeyPair.generate()
 
         let protocolStore = InMemorySignalProtocolStore(identity: identityKeyPair,
-                                                        deviceId: UInt32(bitPattern: deviceId))
+                                                        registrationId: UInt32(registrationId))
 
         sessionStore = protocolStore
         preKeyStore = protocolStore
         signedPreKeyStore = protocolStore
         identityStore = protocolStore
+        senderKeyStore = protocolStore
     }
 
     func createSecretSessionCipher() throws -> SMKSecretSessionCipher {
         return try SMKSecretSessionCipher(sessionStore: sessionStore,
-                                      preKeyStore: preKeyStore,
-                                      signedPreKeyStore: signedPreKeyStore,
-                                      identityStore: identityStore)
+                                          preKeyStore: preKeyStore,
+                                          signedPreKeyStore: signedPreKeyStore,
+                                          identityStore: identityStore,
+                                          senderKeyStore: senderKeyStore)
     }
 
     func generateMockPreKey() -> PreKeyRecord {
@@ -100,14 +106,14 @@ class MockClient: NSObject {
         let bobSignedPreKey = bobMockClient.generateMockSignedPreKey()
 
         // PreKeyBundle bobBundle             = new PreKeyBundle(1, 1, 1, bobPreKey.getPublicKey(), 2, bobSignedPreKey.getKeyPair().getPublicKey(), bobSignedPreKey.getSignature(), bobIdentityKey.getPublicKey());
-        let bobBundle = try! SignalClient.PreKeyBundle(registrationId: UInt32(bitPattern: bobMockClient.registrationId),
-                                                       deviceId: UInt32(bitPattern: bobMockClient.deviceId),
-                                                       prekeyId: bobPreKey.id,
-                                                       prekey: bobPreKey.publicKey,
-                                                       signedPrekeyId: bobSignedPreKey.id,
-                                                       signedPrekey: bobSignedPreKey.publicKey,
-                                                       signedPrekeySignature: bobSignedPreKey.signature,
-                                                       identity: bobIdentityKey.identityKey)
+        let bobBundle = try! PreKeyBundle(registrationId: UInt32(bitPattern: bobMockClient.registrationId),
+                                          deviceId: UInt32(bitPattern: bobMockClient.deviceId),
+                                          prekeyId: bobPreKey.id,
+                                          prekey: bobPreKey.publicKey,
+                                          signedPrekeyId: bobSignedPreKey.id,
+                                          signedPrekey: bobSignedPreKey.publicKey,
+                                          signedPrekeySignature: bobSignedPreKey.signature,
+                                          identity: bobIdentityKey.identityKey)
 
         // SessionBuilder aliceSessionBuilder = new SessionBuilder(aliceStore, new SignalProtocolAddress("+14152222222", 1));
         // aliceSessionBuilder.process(bobBundle);