Don't start expiration timer until message is sent.

Started extracting a MessageSender class from TSMessagesManager+send for
easier testability and in hopes of further slimming down that son of a
gun.

// FREEBIE

Example/TSKitiOSTestApp/TSKitiOSTestApp.xcodeproj/project.pbxproj

@@ -12,6 +12,9 @@
 		450E3C9A1D96DD2600BF4EB6 /* OWSDisappearingMessagesJobTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 450E3C991D96DD2600BF4EB6 /* OWSDisappearingMessagesJobTest.m */; };
 		452EE6CF1D4A754C00E934BA /* TSThreadTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 452EE6CE1D4A754C00E934BA /* TSThreadTest.m */; };
 		452EE6D51D4AC43300E934BA /* OWSOrphanedDataCleanerTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 452EE6D41D4AC43300E934BA /* OWSOrphanedDataCleanerTest.m */; };
+		453E1FCF1DA8313100DDD7B7 /* OWSMessageSenderTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 453E1FCE1DA8313100DDD7B7 /* OWSMessageSenderTest.m */; };
+		453E1FD81DA83E1000DDD7B7 /* OWSFakeContactsManager.m in Sources */ = {isa = PBXBuildFile; fileRef = 453E1FD71DA83E1000DDD7B7 /* OWSFakeContactsManager.m */; };
+		453E1FDB1DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.m in Sources */ = {isa = PBXBuildFile; fileRef = 453E1FDA1DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.m */; };
 		454021ED1D960ABF00F2126D /* OWSDisappearingMessageFinderTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 454021EC1D960ABF00F2126D /* OWSDisappearingMessageFinderTest.m */; };
 		45458B751CC342B600A02153 /* SignedPreKeyDeletionTests.m in Sources */ = {isa = PBXBuildFile; fileRef = 45458B6A1CC342B600A02153 /* SignedPreKeyDeletionTests.m */; };
 		45458B761CC342B600A02153 /* TSAttachmentsTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 45458B6C1CC342B600A02153 /* TSAttachmentsTest.m */; };
@@ -21,6 +24,7 @@
 		45458B7A1CC342B600A02153 /* TSStorageSignedPreKeyStore.m in Sources */ = {isa = PBXBuildFile; fileRef = 45458B711CC342B600A02153 /* TSStorageSignedPreKeyStore.m */; };
 		45458B7B1CC342B600A02153 /* CryptographyTests.m in Sources */ = {isa = PBXBuildFile; fileRef = 45458B731CC342B600A02153 /* CryptographyTests.m */; };
 		45458B7C1CC342B600A02153 /* MessagePaddingTests.m in Sources */ = {isa = PBXBuildFile; fileRef = 45458B741CC342B600A02153 /* MessagePaddingTests.m */; };
+		45731A6C1DA87AA1007E22AA /* TSOutgoingMessageTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 45731A6B1DA87AA1007E22AA /* TSOutgoingMessageTest.m */; };
 		459850C11D22C6F2006FFEDB /* PhoneNumberTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 459850C01D22C6F2006FFEDB /* PhoneNumberTest.m */; };
 		45A856AC1D220BFF0056CD4D /* TSAttributesTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 45A856AB1D220BFF0056CD4D /* TSAttributesTest.m */; };
 		45B700971D9841E400269FFD /* OWSDisappearingMessagesConfigurationTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 45B700961D9841E400269FFD /* OWSDisappearingMessagesConfigurationTest.m */; };
@@ -56,6 +60,11 @@
 		450E3C991D96DD2600BF4EB6 /* OWSDisappearingMessagesJobTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = OWSDisappearingMessagesJobTest.m; path = ../../../tests/Messages/OWSDisappearingMessagesJobTest.m; sourceTree = "<group>"; };
 		452EE6CE1D4A754C00E934BA /* TSThreadTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = TSThreadTest.m; path = ../../../tests/Contacts/TSThreadTest.m; sourceTree = "<group>"; };
 		452EE6D41D4AC43300E934BA /* OWSOrphanedDataCleanerTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = OWSOrphanedDataCleanerTest.m; sourceTree = "<group>"; };
+		453E1FCE1DA8313100DDD7B7 /* OWSMessageSenderTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = OWSMessageSenderTest.m; path = ../../../tests/Messages/OWSMessageSenderTest.m; sourceTree = "<group>"; };
+		453E1FD61DA83E1000DDD7B7 /* OWSFakeContactsManager.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; name = OWSFakeContactsManager.h; path = ../../../tests/TestSupport/Fakes/OWSFakeContactsManager.h; sourceTree = "<group>"; };
+		453E1FD71DA83E1000DDD7B7 /* OWSFakeContactsManager.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = OWSFakeContactsManager.m; path = ../../../tests/TestSupport/Fakes/OWSFakeContactsManager.m; sourceTree = "<group>"; };
+		453E1FD91DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; name = OWSFakeContactsUpdater.h; path = ../../../tests/TestSupport/Fakes/OWSFakeContactsUpdater.h; sourceTree = "<group>"; };
+		453E1FDA1DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = OWSFakeContactsUpdater.m; path = ../../../tests/TestSupport/Fakes/OWSFakeContactsUpdater.m; sourceTree = "<group>"; };
 		454021EC1D960ABF00F2126D /* OWSDisappearingMessageFinderTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = OWSDisappearingMessageFinderTest.m; path = ../../../tests/Messages/OWSDisappearingMessageFinderTest.m; sourceTree = "<group>"; };
 		45458B6A1CC342B600A02153 /* SignedPreKeyDeletionTests.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = SignedPreKeyDeletionTests.m; sourceTree = "<group>"; };
 		45458B6C1CC342B600A02153 /* TSAttachmentsTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = TSAttachmentsTest.m; sourceTree = "<group>"; };
@@ -65,6 +74,7 @@
 		45458B711CC342B600A02153 /* TSStorageSignedPreKeyStore.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = TSStorageSignedPreKeyStore.m; sourceTree = "<group>"; };
 		45458B731CC342B600A02153 /* CryptographyTests.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = CryptographyTests.m; sourceTree = "<group>"; };
 		45458B741CC342B600A02153 /* MessagePaddingTests.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = MessagePaddingTests.m; sourceTree = "<group>"; };
+		45731A6B1DA87AA1007E22AA /* TSOutgoingMessageTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = TSOutgoingMessageTest.m; path = ../../../tests/Messages/Interactions/TSOutgoingMessageTest.m; sourceTree = "<group>"; };
 		459850C01D22C6F2006FFEDB /* PhoneNumberTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; name = PhoneNumberTest.m; path = ../../../tests/Contacts/PhoneNumberTest.m; sourceTree = "<group>"; };
 		459FE0DA1D4AD49E00E1071A /* TSKitiOSTestApp-Prefix.pch */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; path = "TSKitiOSTestApp-Prefix.pch"; sourceTree = "<group>"; };
 		45A856AB1D220BFF0056CD4D /* TSAttributesTest.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = TSAttributesTest.m; sourceTree = "<group>"; };
@@ -111,6 +121,25 @@
 /* End PBXFrameworksBuildPhase section */
 
 /* Begin PBXGroup section */
+		453E1FD41DA83DD500DDD7B7 /* TestSupport */ = {
+			isa = PBXGroup;
+			children = (
+				453E1FD51DA83DDC00DDD7B7 /* Fakes */,
+			);
+			name = TestSupport;
+			sourceTree = "<group>";
+		};
+		453E1FD51DA83DDC00DDD7B7 /* Fakes */ = {
+			isa = PBXGroup;
+			children = (
+				453E1FD61DA83E1000DDD7B7 /* OWSFakeContactsManager.h */,
+				453E1FD71DA83E1000DDD7B7 /* OWSFakeContactsManager.m */,
+				453E1FD91DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.h */,
+				453E1FDA1DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.m */,
+			);
+			name = Fakes;
+			sourceTree = "<group>";
+		};
 		45458B691CC342B600A02153 /* Account */ = {
 			isa = PBXGroup;
 			children = (
@@ -178,6 +207,7 @@
 				45C6A0981D2F0264007D8AC0 /* Interactions */,
 				45046FDF1D95A6130015EFF2 /* TSMessagesManagerTest.m */,
 				454021EC1D960ABF00F2126D /* OWSDisappearingMessageFinderTest.m */,
+				453E1FCE1DA8313100DDD7B7 /* OWSMessageSenderTest.m */,
 			);
 			name = Messages;
 			sourceTree = "<group>";
@@ -186,6 +216,7 @@
 			isa = PBXGroup;
 			children = (
 				45C6A0991D2F029B007D8AC0 /* TSMessageTest.m */,
+				45731A6B1DA87AA1007E22AA /* TSOutgoingMessageTest.m */,
 			);
 			name = Interactions;
 			sourceTree = "<group>";
@@ -268,6 +299,7 @@
 		B6273DED1C13A2E500738558 /* TSKitiOSTestAppTests */ = {
 			isa = PBXGroup;
 			children = (
+				453E1FD41DA83DD500DDD7B7 /* TestSupport */,
 				45458B691CC342B600A02153 /* Account */,
 				45458B6B1CC342B600A02153 /* Attachments */,
 				459850BF1D22C6C4006FFEDB /* Contacts */,
@@ -503,13 +535,17 @@
 				452EE6CF1D4A754C00E934BA /* TSThreadTest.m in Sources */,
 				45458B761CC342B600A02153 /* TSAttachmentsTest.m in Sources */,
 				45C6A09A1D2F029B007D8AC0 /* TSMessageTest.m in Sources */,
+				453E1FCF1DA8313100DDD7B7 /* OWSMessageSenderTest.m in Sources */,
 				459850C11D22C6F2006FFEDB /* PhoneNumberTest.m in Sources */,
 				45458B7A1CC342B600A02153 /* TSStorageSignedPreKeyStore.m in Sources */,
+				453E1FDB1DA83EFB00DDD7B7 /* OWSFakeContactsUpdater.m in Sources */,
+				453E1FD81DA83E1000DDD7B7 /* OWSFakeContactsManager.m in Sources */,
 				454021ED1D960ABF00F2126D /* OWSDisappearingMessageFinderTest.m in Sources */,
 				45458B771CC342B600A02153 /* TSMessageStorageTests.m in Sources */,
 				45046FE01D95A6130015EFF2 /* TSMessagesManagerTest.m in Sources */,
 				45458B7C1CC342B600A02153 /* MessagePaddingTests.m in Sources */,
 				45A856AC1D220BFF0056CD4D /* TSAttributesTest.m in Sources */,
+				45731A6C1DA87AA1007E22AA /* TSOutgoingMessageTest.m in Sources */,
 				6323E339D5B8F4CB77EB3ED4 /* SignalRecipientTest.m in Sources */,
 				6323E1F7730289398452E5C5 /* OWSFingerprintTest.m in Sources */,
 			);

src/Messages/Interactions/TSMessage.h

@@ -26,6 +26,7 @@ typedef NS_ENUM(NSInteger, TSGroupMetaMessage) {
 @property (nonatomic) uint64_t expireStartedAt;
 @property (nonatomic, readonly) uint64_t expiresAt;
 @property (nonatomic, readonly) BOOL isExpiringMessage;
+@property (nonatomic, readonly) BOOL shouldStartExpireTimer;
 
 - (instancetype)initWithTimestamp:(uint64_t)timestamp;
 

src/Messages/Interactions/TSMessage.m

@@ -146,6 +146,11 @@ static const NSUInteger OWSMessageSchemaVersion = 3;
     [self updateExpiresAt];
 }
 
+- (BOOL)shouldStartExpireTimer
+{
+    return self.isExpiringMessage;
+}
+
 // TODO a downloaded media doesn't start counting until download is complete.
 - (void)updateExpiresAt
 {

src/Messages/Interactions/TSOutgoingMessage.m

@@ -52,13 +52,12 @@ NS_ASSUME_NONNULL_BEGIN
                     attachmentIds:(NSMutableArray<NSString *> *)attachmentIds
                  expiresInSeconds:(uint32_t)expiresInSeconds
 {
-    uint64_t now = [NSDate ows_millisecondTimeStamp];
     return [self initWithTimestamp:timestamp
                           inThread:thread
                        messageBody:body
                      attachmentIds:attachmentIds
                   expiresInSeconds:expiresInSeconds
-                   expireStartedAt:now];
+                   expireStartedAt:0];
 }
 
 - (instancetype)initWithTimestamp:(uint64_t)timestamp
@@ -95,6 +94,18 @@ NS_ASSUME_NONNULL_BEGIN
     return self.thread.contactIdentifier;
 }
 
+- (BOOL)shouldStartExpireTimer
+{
+    switch (self.messageState) {
+        case TSOutgoingMessageStateSent:
+        case TSOutgoingMessageStateDelivered:
+            return self.isExpiringMessage;
+        case TSOutgoingMessageStateAttemptingOut:
+        case TSOutgoingMessageStateUnsent:
+            return NO;
+    }
+}
+
 - (OWSSignalServiceProtosDataMessageBuilder *)dataMessageBuilder
 {
     TSThread *thread = self.thread;

src/Messages/OWSDisappearingMessagesFinder.m

@@ -4,6 +4,7 @@
 #import "OWSDisappearingMessagesFinder.h"
 #import "NSDate+millisecondTimeStamp.h"
 #import "TSMessage.h"
+#import "TSOutgoingMessage.h"
 #import "TSStorageManager.h"
 #import "TSThread.h"
 #import <YapDatabase/YapDatabaseConnection.h>
@@ -14,7 +15,7 @@ NS_ASSUME_NONNULL_BEGIN
 
 static NSString *const OWSDisappearingMessageFinderThreadIdColumn = @"thread_id";
 static NSString *const OWSDisappearingMessageFinderExpiresAtColumn = @"expires_at";
-static NSString *const OWSDisappearingMessageFinderExpiresAtIndex = @"index_messages_on_expires_at_and_thread_id";
+static NSString *const OWSDisappearingMessageFinderExpiresAtIndex = @"index_messages_on_expires_at_and_thread_id_v2";
 
 @interface OWSDisappearingMessagesFinder ()
 
@@ -184,13 +185,17 @@ static NSString *const OWSDisappearingMessageFinderExpiresAtIndex = @"index_mess
             NSString *collection,
             NSString *key,
             id object) {
-            if ([object isKindOfClass:[TSMessage class]]) {
+            if (![object isKindOfClass:[TSMessage class]]) {
-                TSMessage *message = (TSMessage *)object;
+                return;
-                if (message.expiresInSeconds > 0) {
-                    dict[OWSDisappearingMessageFinderExpiresAtColumn] = @(message.expiresAt);
-                    dict[OWSDisappearingMessageFinderThreadIdColumn] = message.uniqueThreadId;
-                } // else don't index non-expiring messages.
             }
+            TSMessage *message = (TSMessage *)object;
+
+            if (!message.shouldStartExpireTimer) {
+                return;
+            }
+
+            dict[OWSDisappearingMessageFinderExpiresAtColumn] = @(message.expiresAt);
+            dict[OWSDisappearingMessageFinderThreadIdColumn] = message.uniqueThreadId;
         }];
 
     return [[YapDatabaseSecondaryIndex alloc] initWithSetup:setup handler:handler];

src/Messages/OWSMessageSender.h

@@ -0,0 +1,24 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+NS_ASSUME_NONNULL_BEGIN
+
+@class TSOutgoingMessage;
+@class TSNetworkManager;
+@class TSStorageManager;
+@class ContactsUpdater;
+@protocol ContactsManagerProtocol;
+
+@interface OWSMessageSender : NSObject
+
+- (instancetype)initWithMessage:(TSOutgoingMessage *)message
+                 networkManager:(TSNetworkManager *)networkManager
+                 storageManager:(TSStorageManager *)storageManager
+                contactsManager:(id<ContactsManagerProtocol>)contactsManager
+                contactsUpdater:(ContactsUpdater *)contactsUpdater;
+
+- (void)sendWithSuccess:(void (^)())successBlock failure:(void (^)(NSError *error))failureBlock;
+
+@end
+
+NS_ASSUME_NONNULL_END

src/Messages/OWSMessageSender.m

@@ -0,0 +1,60 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "OWSMessageSender.h"
+#import "OWSError.h"
+#import "TSMessagesManager+sendMessages.h"
+#import "TSNetworkManager.h"
+#import "TSOutgoingMessage.h"
+#import "TSThread.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface OWSMessageSender ()
+
+@property (nonatomic, readonly) TSOutgoingMessage *message;
+@property (nonatomic, readonly) TSNetworkManager *networkManager;
+@property (nonatomic, readonly) TSMessagesManager *messagesManager;
+
+@end
+
+@implementation OWSMessageSender
+
+- (instancetype)initWithMessage:(TSOutgoingMessage *)message
+                 networkManager:(TSNetworkManager *)networkManager
+                 storageManager:(TSStorageManager *)storageManager
+                contactsManager:(id<ContactsManagerProtocol>)contactsManager
+                contactsUpdater:(ContactsUpdater *)contactsUpdater
+{
+    self = [super init];
+    if (!self) {
+        return self;
+    }
+
+    _message = message;
+    _networkManager = networkManager;
+    _messagesManager = [[TSMessagesManager alloc] initWithNetworkManager:networkManager
+                                                          storageManager:storageManager
+                                                         contactsManager:contactsManager
+                                                         contactsUpdater:contactsUpdater];
+    return self;
+}
+
+- (void)sendWithSuccess:(void (^)())successBlock failure:(void (^)(NSError *error))failureBlock
+{
+    [self.messagesManager sendMessage:self.message
+        inThread:self.message.thread
+        success:^{
+            successBlock();
+        }
+        failure:^{
+            NSString *localizedError
+                = NSLocalizedString(@"NOTIFICATION_SEND_FAILED", @"Generic notice when message failed to send.");
+            NSError *error = OWSErrorWithCodeDescription(OWSErrorCodeFailedToSendOutgoingMessage, localizedError);
+            failureBlock(error);
+        }];
+}
+
+@end
+
+NS_ASSUME_NONNULL_END

src/Messages/TSMessagesManager+sendMessages.m

@@ -137,12 +137,8 @@ dispatch_queue_t sendingQueue() {
                   ? [TSAccountManager localNumber]
                   : contactThread.contactIdentifier;
 
-              __block SignalRecipient *recipient;
+              __block SignalRecipient *recipient =
-              [self.dbConnection readWithBlock:^(YapDatabaseReadTransaction *transaction) {
+                  [SignalRecipient recipientWithTextSecureIdentifier:recipientContactId];
-                  recipient = [SignalRecipient recipientWithTextSecureIdentifier:recipientContactId
-                                                                 withTransaction:transaction];
-              }];
-
               if (!recipient) {
                   [self.contactsUpdater synchronousLookup:contactThread.contactIdentifier
                       success:^(SignalRecipient *recip) {
@@ -258,7 +254,7 @@ dispatch_queue_t sendingQueue() {
                     self.logTag,
                     exception);
                 [self processException:exception outgoingMessage:message inThread:thread];
-                return;
+                BLOCK_SAFE_RUN(failureBlock);
             }
         }
 
@@ -317,6 +313,7 @@ dispatch_queue_t sendingQueue() {
 
                         if (!responseData) {
                             DDLogWarn(@"Stale devices but server didn't specify devices in response.");
+                            BLOCK_SAFE_RUN(failureBlock);
                             return;
                         }
 

src/Protocols/ContactsManagerProtocol.h

@@ -3,6 +3,7 @@
 
 @class PhoneNumber;
 @class Contact;
+@class UIImage;
 
 @protocol ContactsManagerProtocol <NSObject>
 

src/Util/OWSError.h

@@ -10,8 +10,8 @@ typedef NS_ENUM(NSInteger, OWSErrorCode) {
     OWSErrorCodeFailedToDecodeJson = 13,
     OWSErrorCodeFailedToEncodeJson = 14,
     OWSErrorCodeFailedToDecodeQR = 15,
-    OWSErrorCodePrivacyVerificationFailure = 20
+    OWSErrorCodePrivacyVerificationFailure = 20,
-
+    OWSErrorCodeFailedToSendOutgoingMessage = 30
 };
 
 extern NSError *OWSErrorWithCodeDescription(OWSErrorCode code, NSString *description);

tests/Messages/Interactions/TSOutgoingMessageTest.m

@@ -0,0 +1,77 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "TSContactThread.h"
+#import "TSOutgoingMessage.h"
+#import <XCTest/XCTest.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface TSOutgoingMessageTest : XCTestCase
+
+@property (nonatomic) TSContactThread *thread;
+
+@end
+
+@implementation TSOutgoingMessageTest
+
+- (void)setUp
+{
+    [super setUp];
+    self.thread = [[TSContactThread alloc] initWithUniqueId:@"fake-thread-id"];
+}
+
+- (void)testShouldNotStartExpireTimerWithMessageThatDoesNotExpire
+{
+    TSOutgoingMessage *message = [[TSOutgoingMessage alloc] initWithTimestamp:100 inThread:self.thread messageBody:nil];
+    XCTAssertFalse(message.shouldStartExpireTimer);
+}
+
+- (void)testShouldStartExpireTimerWithSentMessage
+{
+    TSOutgoingMessage *message = [[TSOutgoingMessage alloc] initWithTimestamp:100
+                                                                     inThread:self.thread
+                                                                  messageBody:nil
+                                                                attachmentIds:[NSMutableArray new]
+                                                             expiresInSeconds:10];
+    message.messageState = TSOutgoingMessageStateSent;
+    XCTAssert(message.shouldStartExpireTimer);
+}
+
+- (void)testShouldStartExpireTimerWithDeliveredMessage
+{
+    TSOutgoingMessage *message = [[TSOutgoingMessage alloc] initWithTimestamp:100
+                                                                     inThread:self.thread
+                                                                  messageBody:nil
+                                                                attachmentIds:[NSMutableArray new]
+                                                             expiresInSeconds:10];
+    message.messageState = TSOutgoingMessageStateDelivered;
+    XCTAssert(message.shouldStartExpireTimer);
+}
+
+- (void)testShouldNotStartExpireTimerWithUnsentMessage
+{
+    TSOutgoingMessage *message = [[TSOutgoingMessage alloc] initWithTimestamp:100
+                                                                     inThread:self.thread
+                                                                  messageBody:nil
+                                                                attachmentIds:[NSMutableArray new]
+                                                             expiresInSeconds:10];
+    message.messageState = TSOutgoingMessageStateUnsent;
+    XCTAssertFalse(message.shouldStartExpireTimer);
+}
+
+- (void)testShouldNotStartExpireTimerWithAttemptingOutMessage
+{
+    TSOutgoingMessage *message = [[TSOutgoingMessage alloc] initWithTimestamp:100
+                                                                     inThread:self.thread
+                                                                  messageBody:nil
+                                                                attachmentIds:[NSMutableArray new]
+                                                             expiresInSeconds:10];
+    message.messageState = TSOutgoingMessageStateAttemptingOut;
+    XCTAssertFalse(message.shouldStartExpireTimer);
+}
+
+
+@end
+
+NS_ASSUME_NONNULL_END

tests/Messages/OWSMessageSenderTest.m

@@ -0,0 +1,170 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "OWSError.h"
+#import "OWSFakeContactsManager.h"
+#import "OWSFakeContactsUpdater.h"
+#import "OWSMessageSender.h"
+#import "TSContactThread.h"
+#import "TSNetworkManager.h"
+#import "TSOutgoingMessage.h"
+#import "TSStorageManager.h"
+#import <XCTest/XCTest.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface OWSFakeURLSessionDataTask : NSURLSessionDataTask
+
+@property (copy) NSHTTPURLResponse *response;
+
+- (instancetype)initWithStatusCode:(long)statusCode;
+
+@end
+
+@implementation OWSFakeURLSessionDataTask
+
+@synthesize response = _response;
+
+- (instancetype)initWithStatusCode:(long)statusCode
+{
+    self = [super init];
+
+    if (!self) {
+        return self;
+    }
+
+    NSURL *fakeURL = [NSURL URLWithString:@"http://127.0.0.1"];
+    _response = [[NSHTTPURLResponse alloc] initWithURL:fakeURL statusCode:statusCode HTTPVersion:nil headerFields:nil];
+
+    return self;
+}
+
+@end
+
+@interface OWSMessageSenderFakeNetworkManager : TSNetworkManager
+
+- (instancetype)init NS_UNAVAILABLE;
+- (instancetype)initWithSuccess:(BOOL)shouldSucceed NS_DESIGNATED_INITIALIZER;
+
+@property (nonatomic, readonly) BOOL shouldSucceed;
+
+@end
+
+@implementation OWSMessageSenderFakeNetworkManager
+
+- (instancetype)initWithSuccess:(BOOL)shouldSucceed
+{
+    // intentionally skipping super init which explodes without setup.
+    _shouldSucceed = shouldSucceed;
+
+    return self;
+}
+
+- (void)makeRequest:(TSRequest *)request
+            success:(void (^)(NSURLSessionDataTask *task, id responseObject))success
+            failure:(void (^)(NSURLSessionDataTask *task, NSError *error))failure
+{
+    if ([request isKindOfClass:[TSSubmitMessageRequest class]]) {
+        if (self.shouldSucceed) {
+            success([NSURLSessionDataTask new], @{});
+        } else {
+            NSError *error
+                = OWSErrorWithCodeDescription(OWSErrorCodeFailedToSendOutgoingMessage, @"fake error description");
+            OWSFakeURLSessionDataTask *task = [[OWSFakeURLSessionDataTask alloc] initWithStatusCode:500];
+            failure(task, error);
+        }
+    } else {
+        NSLog(@"Ignoring unhandled request: %@", request);
+    }
+}
+
+@end
+
+@interface OWSMessageSenderTest : XCTestCase
+
+@property (nonatomic) TSThread *thread;
+@property (nonatomic) TSOutgoingMessage *expiringMessage;
+@property (nonatomic) OWSMessageSenderFakeNetworkManager *networkManager;
+
+@end
+
+@implementation OWSMessageSenderTest
+
+- (void)setUp
+{
+    [super setUp];
+
+    self.thread = [[TSContactThread alloc] initWithUniqueId:@"fake-thread-id"];
+    [self.thread save];
+
+    self.expiringMessage = [[TSOutgoingMessage alloc] initWithTimestamp:1
+                                                               inThread:self.thread
+                                                            messageBody:@"outgoing message"
+                                                          attachmentIds:[NSMutableArray new]
+                                                       expiresInSeconds:30];
+    [self.expiringMessage save];
+}
+
+- (void)testExpiringMessageTimerStartsOnSuccess
+{
+    TSNetworkManager *networkManager = [[OWSMessageSenderFakeNetworkManager alloc] initWithSuccess:YES];
+    OWSMessageSender *messageSender = [[OWSMessageSender alloc] initWithMessage:self.expiringMessage
+                                                                 networkManager:networkManager
+                                                                 storageManager:[TSStorageManager sharedManager]
+                                                                contactsManager:[OWSFakeContactsManager new]
+                                                                contactsUpdater:[OWSFakeContactsUpdater new]];
+
+    // Sanity Check
+    XCTAssertEqual(0, self.expiringMessage.expiresAt);
+
+    XCTestExpectation *messageStartedExpiration = [self expectationWithDescription:@"messageStartedExpiration"];
+    [messageSender sendWithSuccess:^() {
+        if (self.expiringMessage.expiresAt > 0) {
+            [messageStartedExpiration fulfill];
+        } else {
+            XCTFail(@"Message expiration was supposed to start.");
+        }
+    }
+        failure:^(NSError *error) {
+            XCTFail(@"Message failed to send");
+        }];
+
+    [self waitForExpectationsWithTimeout:5
+                                 handler:^(NSError *error) {
+                                     NSLog(@"Expiration timer not set in time.");
+                                 }];
+}
+
+- (void)testExpiringMessageTimerDoesNotStartsOnFailure
+{
+    TSNetworkManager *networkManager = [[OWSMessageSenderFakeNetworkManager alloc] initWithSuccess:NO];
+    OWSMessageSender *messageSender = [[OWSMessageSender alloc] initWithMessage:self.expiringMessage
+                                                                 networkManager:networkManager
+                                                                 storageManager:[TSStorageManager sharedManager]
+                                                                contactsManager:[OWSFakeContactsManager new]
+                                                                contactsUpdater:[OWSFakeContactsUpdater new]];
+
+    // Sanity Check
+    XCTAssertEqual(0, self.expiringMessage.expiresAt);
+
+    XCTestExpectation *messageDidNotStartExpiration = [self expectationWithDescription:@"messageStartedExpiration"];
+    [messageSender sendWithSuccess:^() {
+        XCTFail(@"Message sending was supposed to fail.");
+    }
+        failure:^(NSError *error) {
+            if (self.expiringMessage.expiresAt == 0) {
+                [messageDidNotStartExpiration fulfill];
+            } else {
+                XCTFail(@"Message expiration was not supposed to start.");
+            }
+        }];
+
+    [self waitForExpectationsWithTimeout:5
+                                 handler:^(NSError *error) {
+                                     NSLog(@"Wasn't able to verify.");
+                                 }];
+}
+
+@end
+
+NS_ASSUME_NONNULL_END

tests/Messages/TSMessagesManagerTest.m

@@ -3,12 +3,14 @@
 
 #import <XCTest/XCTest.h>
 
+#import "ContactsManagerProtocol.h"
 #import "ContactsUpdater.h"
+#import "OWSFakeContactsManager.h"
+#import "OWSFakeContactsUpdater.h"
 #import "OWSSignalServiceProtos.pb.h"
 #import "TSMessagesManager.h"
 #import "TSNetworkManager.h"
 #import "TSStorageManager.h"
-#import "ContactsManagerProtocol.h"
 #import "objc/runtime.h"
 
 @interface TSMessagesManagerTest : XCTestCase
@@ -93,15 +95,15 @@
 
 - (instancetype)initWithExpectation:(XCTestExpectation *)messageWasSubmitted;
 
-@property XCTestExpectation *messageWasSubmitted;
+@property XCTestExpectation *expectation;
 
 @end
 
 @implementation OWSTSMessagesManagerTestNetworkManager
 
-- (instancetype)initWithExpectation:(XCTestExpectation *)messageWasSubmitted
+- (instancetype)initWithExpectation:(XCTestExpectation *)expectation
 {
-    _messageWasSubmitted = messageWasSubmitted;
+    _expectation = expectation;
 
     return self;
 }
@@ -114,7 +116,7 @@
         NSDictionary *fakeResponse = @{ @"id" : @(1234), @"location" : @"fake-location" };
         success(nil, fakeResponse);
     } else if ([request isKindOfClass:[TSSubmitMessageRequest class]]) {
-        [self.messageWasSubmitted fulfill];
+        [self.expectation fulfill];
     } else {
         NSLog(@"Ignoring unhandled request: %@", request);
     }
@@ -122,56 +124,6 @@
 
 @end
 
-@interface OWSFakeContactsUpdater : ContactsUpdater
-
-@end
-
-@implementation OWSFakeContactsUpdater
-
-- (void)synchronousLookup:(NSString *)identifier
-                  success:(void (^)(SignalRecipient *))success
-                  failure:(void (^)(NSError *error))failure
-{
-    NSLog(@"Fake contact lookup.");
-    SignalRecipient *fakeRecipient =
-        [[SignalRecipient alloc] initWithTextSecureIdentifier:@"fake-recipient-id" relay:nil supportsVoice:YES];
-    success(fakeRecipient);
-}
-
-@end
-
-@interface OWSFakeContactsManager : NSObject <ContactsManagerProtocol>
-
-@end
-
-/**
- * I don't know that this test relys on any of the specific behavior in this implementation.
- * We're just trying to avoid setting up/accessing the TSEnv global. ~mjk
- */
-@implementation OWSFakeContactsManager
-
-- (NSString *)nameStringForPhoneIdentifier:(NSString *)phoneNumber
-{
-    return @"Fake name";
-}
-
-- (NSArray<Contact *> *)signalContacts
-{
-    return @[];
-}
-
-+ (BOOL)name:(NSString *)nameString matchesQuery:(NSString *)queryString
-{
-    return YES;
-}
-
-- (UIImage *)imageForPhoneIdentifier:(NSString *)phoneNumber
-{
-    return nil;
-}
-
-@end
-
 @implementation TSMessagesManagerTest
 
 - (void)testIncomingSyncContactMessage
@@ -202,5 +154,4 @@
                                  }];
 }
 
-
 @end

tests/TestSupport/Fakes/OWSFakeContactsManager.h

@@ -0,0 +1,12 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "ContactsManagerProtocol.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface OWSFakeContactsManager : NSObject <ContactsManagerProtocol>
+
+@end
+
+NS_ASSUME_NONNULL_END

tests/TestSupport/Fakes/OWSFakeContactsManager.m

@@ -0,0 +1,34 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "OWSFakeContactsManager.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@class UIImage;
+
+@implementation OWSFakeContactsManager
+
+- (NSString *)nameStringForPhoneIdentifier:(NSString *)phoneNumber
+{
+    return @"Fake name";
+}
+
+- (NSArray<Contact *> *)signalContacts
+{
+    return @[];
+}
+
++ (BOOL)name:(NSString *)nameString matchesQuery:(NSString *)queryString
+{
+    return YES;
+}
+
+- (nullable UIImage *)imageForPhoneIdentifier:(NSString *)phoneNumber
+{
+    return nil;
+}
+
+@end
+
+NS_ASSUME_NONNULL_END

tests/TestSupport/Fakes/OWSFakeContactsUpdater.h

@@ -0,0 +1,12 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "ContactsUpdater.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface OWSFakeContactsUpdater : ContactsUpdater
+
+@end
+
+NS_ASSUME_NONNULL_END

tests/TestSupport/Fakes/OWSFakeContactsUpdater.m

@@ -0,0 +1,23 @@
+//  Created by Michael Kirk on 10/7/16.
+//  Copyright © 2016 Open Whisper Systems. All rights reserved.
+
+#import "OWSFakeContactsUpdater.h"
+#import "SignalRecipient.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@implementation OWSFakeContactsUpdater
+
+- (void)synchronousLookup:(NSString *)identifier
+                  success:(void (^)(SignalRecipient *))success
+                  failure:(void (^)(NSError *error))failure
+{
+    NSLog(@"[OWSFakeContactsUpdater] Faking contact lookup.");
+    SignalRecipient *fakeRecipient =
+        [[SignalRecipient alloc] initWithTextSecureIdentifier:@"fake-recipient-id" relay:nil supportsVoice:YES];
+    success(fakeRecipient);
+}
+
+@end
+
+NS_ASSUME_NONNULL_END