Reusable UploadOperation based on extracted OWSOperation

// FREEBIE

Signal/src/ViewControllers/ConversationView/Cells/AttachmentUploadView.m

@@ -5,9 +5,9 @@
 #import "AttachmentUploadView.h"
 #import "OWSBezierPathView.h"
 #import "OWSProgressView.h"
-#import "OWSUploadingService.h"
-#import "TSAttachmentStream.h"
-#import "UIView+OWS.h"
+#import <SignalMessaging/UIView+OWS.h>
+#import <SignalServiceKit/OWSUploadOperation.h>
+#import <SignalServiceKit/TSAttachmentStream.h>
 
 NS_ASSUME_NONNULL_BEGIN
 

Signal/src/views/QuotedReplyPreview.swift

@@ -52,15 +52,16 @@ class QuotedReplyPreview: UIView {
         }()
 
         let thumbnailView: UIView? = {
-            if let image = quotedMessage.thumbnailImage() {
-                let imageView = UIImageView(image: image)
-                imageView.contentMode = .scaleAspectFill
-                imageView.autoPinToSquareAspectRatio()
-                imageView.layer.cornerRadius = 3.0
-                imageView.clipsToBounds = true
-
-                return imageView
-            }
+            // FIXME TODO
+//            if let image = quotedMessage.thumbnailImage() {
+//                let imageView = UIImageView(image: image)
+//                imageView.contentMode = .scaleAspectFill
+//                imageView.autoPinToSquareAspectRatio()
+//                imageView.layer.cornerRadius = 3.0
+//                imageView.clipsToBounds = true
+//
+//                return imageView
+//            }
             return nil
         }()
 

SignalMessaging/environment/migrations/OWS106EnsureProfileComplete.swift

@@ -92,8 +92,7 @@ public class OWS106EnsureProfileComplete: OWSDatabaseMigration {
             let (promise, fulfill, reject) = Promise<Void>.pending()
 
             guard let networkManager = Environment.current().networkManager else {
-                owsFail("\(TAG) network manager was unexpectedly not set")
-                return Promise(error: OWSErrorMakeAssertionError())
+                return Promise(error: OWSErrorMakeAssertionError("\(TAG) network manager was unexpectedly not set"))
             }
 
             ProfileFetcherJob(networkManager: networkManager).getProfile(recipientId: localRecipientId).then { _ -> Void in

SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.m

@@ -394,9 +394,14 @@ NSString *const kTSOutgoingMessageSentRecipientAll = @"kTSOutgoingMessageSentRec
 - (OWSSignalServiceProtosDataMessageBuilder *)dataMessageBuilder
 {
     TSThread *thread = self.thread;
+    OWSAssert(thread);
+    
     OWSSignalServiceProtosDataMessageBuilder *builder = [OWSSignalServiceProtosDataMessageBuilder new];
     [builder setTimestamp:self.timestamp];
     [builder setBody:self.body];
+    [builder setExpireTimer:self.expiresInSeconds];
+    
+    // Group Messages
     BOOL attachmentWasGroupAvatar = NO;
     if ([thread isKindOfClass:[TSGroupThread class]]) {
         TSGroupThread *gThread = (TSGroupThread *)thread;
@@ -426,66 +431,59 @@ NSString *const kTSOutgoingMessageSentRecipientAll = @"kTSOutgoingMessageSentRec
         [groupBuilder setId:gThread.groupModel.groupId];
         [builder setGroup:groupBuilder.build];
     }
+    
+    // Message Attachments
     if (!attachmentWasGroupAvatar) {
         NSMutableArray *attachments = [NSMutableArray new];
         for (NSString *attachmentId in self.attachmentIds) {
-            NSString *sourceFilename = self.attachmentFilenameMap[attachmentId];
+            NSString *_Nullable sourceFilename = self.attachmentFilenameMap[attachmentId];
             [attachments addObject:[self buildAttachmentProtoForAttachmentId:attachmentId filename:sourceFilename]];
         }
         [builder setAttachmentsArray:attachments];
     }
-    [builder setExpireTimer:self.expiresInSeconds];
-    return builder;
-}
-
-// recipientId is nil when building "sent" sync messages for messages
-// sent to groups.
-- (OWSSignalServiceProtosDataMessage *)buildDataMessage:(NSString *_Nullable)recipientId
-{
-    OWSAssert(self.thread);
-
-    OWSSignalServiceProtosDataMessageBuilder *builder = [self dataMessageBuilder];
-    [builder setTimestamp:self.timestamp];
-    [builder addLocalProfileKeyIfNecessary:self.thread recipientId:recipientId];
-
-    if (self.quotedMessage) {
-        OWSSignalServiceProtosDataMessageQuoteBuilder *quoteBuilder =
-            [OWSSignalServiceProtosDataMessageQuoteBuilder new];
-        [quoteBuilder setId:self.quotedMessage.timestamp];
-        [quoteBuilder setAuthor:self.quotedMessage.authorId];
-
+    
+    // Quoted Attachment
+    TSQuotedMessage *quotedMessage = self.quotedMessage;
+    if (quotedMessage) {
+        OWSSignalServiceProtosDataMessageQuoteBuilder *quoteBuilder = [OWSSignalServiceProtosDataMessageQuoteBuilder new];
+        [quoteBuilder setId:quotedMessage.timestamp];
+        [quoteBuilder setAuthor:quotedMessage.authorId];
+        
         BOOL hasQuotedText = NO;
         BOOL hasQuotedAttachment = NO;
         if (self.quotedMessage.body.length > 0) {
-            [quoteBuilder setText:self.quotedMessage.body];
-
             hasQuotedText = YES;
+            [quoteBuilder setText:quotedMessage.body];
         }
 
-        if (self.quotedMessage.contentType.length > 0) {
-
-            OWSSignalServiceProtosAttachmentPointerBuilder *attachmentBuilder =
-                [OWSSignalServiceProtosAttachmentPointerBuilder new];
-            if (self.quotedMessage.thumbnailData.length > 0) {
-                [attachmentBuilder setThumbnail:self.quotedMessage.thumbnailData];
+        if (quotedMessage.thumbnailAttachmentIds.count > 0) {
+            NSMutableArray *thumbnailAttachments = [NSMutableArray new];
+            for (NSString *attachmentId in quotedMessage.thumbnailAttachmentIds) {
+                hasQuotedAttachment = YES;
+                NSString *_Nullable sourceFilename = quotedMessage.thumbnailAttachmentFilenameMap[attachmentId];
+                [thumbnailAttachments addObject:[self buildAttachmentProtoForAttachmentId:attachmentId filename:sourceFilename]];
             }
-            if (self.quotedMessage.sourceFilename.length > 0) {
-                [attachmentBuilder setFileName:self.quotedMessage.sourceFilename];
-            }
-            [attachmentBuilder setContentType:self.quotedMessage.contentType];
-            [quoteBuilder.attachments addObject:[attachmentBuilder build]];
-
-            hasQuotedAttachment = YES;
+            [quoteBuilder setAttachmentsArray:thumbnailAttachments];
         }
-
+        
         if (hasQuotedText || hasQuotedAttachment) {
             [builder setQuoteBuilder:quoteBuilder];
         } else {
             OWSFail(@"%@ Invalid quoted message data.", self.logTag);
         }
     }
+    
+    return builder;
+}
 
-    return [builder build];
+// recipientId is nil when building "sent" sync messages for messages sent to groups.
+- (OWSSignalServiceProtosDataMessage *)buildDataMessage:(NSString *_Nullable)recipientId
+{
+    OWSAssert(self.thread);
+    OWSSignalServiceProtosDataMessageBuilder *builder = [self dataMessageBuilder];
+    [builder addLocalProfileKeyIfNecessary:self.thread recipientId:recipientId];
+    
+    return [[self dataMessageBuilder] build];
 }
 
 - (NSData *)buildPlainTextData:(SignalRecipient *)recipient

SignalServiceKit/src/Messages/Interactions/TSQuotedMessage.h

@@ -6,6 +6,8 @@
 
 NS_ASSUME_NONNULL_BEGIN
 
+@class TSAttachment;
+
 @interface TSQuotedMessage : TSYapDatabaseObject
 
 @property (nonatomic, readonly) uint64_t timestamp;
@@ -15,10 +17,9 @@ NS_ASSUME_NONNULL_BEGIN
 // or attachment with caption.
 @property (nullable, nonatomic, readonly) NSString *body;
 
-// This property should be set IFF we are quoting an attachment message.
-@property (nullable, nonatomic, readonly) NSString *sourceFilename;
-// This property can be set IFF we are quoting an attachment message, but it is optional.
-@property (nullable, nonatomic, readonly) NSData *thumbnailData;
+//// This property can be set IFF we are quoting an attachment message, but it is optional.
+//@property (nullable, nonatomic, readonly) NSData *thumbnailData;
+
 // This is a MIME type.
 //
 // This property should be set IFF we are quoting an attachment message.
@@ -33,7 +34,14 @@ NS_ASSUME_NONNULL_BEGIN
                     thumbnailData:(NSData *_Nullable)thumbnailData
                       contentType:(NSString *_Nullable)contentType;
 
-- (nullable UIImage *)thumbnailImage;
+#pragma mark - Attachments
+
+@property (nonatomic, readonly) NSArray<NSString *> *thumbnailAttachmentIds;
+// A map of attachment id-to-"source" filename.
+@property (nonatomic, readonly) NSMutableDictionary<NSString *, NSString *> *thumbnailAttachmentFilenameMap;
+
+- (BOOL)hasThumbnailAttachments;
+- (nullable TSAttachment *)firstThumbnailAttachmentWithTransaction:(YapDatabaseReadTransaction *)transaction;
 
 @end
 

SignalServiceKit/src/Messages/Interactions/TSQuotedMessage.m

@@ -3,6 +3,7 @@
 //
 
 #import "TSQuotedMessage.h"
+#import "TSAttachment.h"
 
 NS_ASSUME_NONNULL_BEGIN
 
@@ -26,23 +27,50 @@ NS_ASSUME_NONNULL_BEGIN
     _timestamp = timestamp;
     _authorId = authorId;
     _body = body;
-    _sourceFilename = sourceFilename;
-    _thumbnailData = thumbnailData;
+    // TODO get source filename from attachment
+//    _sourceFilename = sourceFilename;
+//    _thumbnailData = thumbnailData;
     _contentType = contentType;
 
     return self;
 }
 
+// TODO maybe this should live closer to the view
 - (nullable UIImage *)thumbnailImage
 {
-    if (self.thumbnailData.length == 0) {
-        return nil;
-    }
+//    if (self.thumbnailData.length == 0) {
+//        return nil;
+//    }
+//
+//    // PERF TODO cache
+//    return [UIImage imageWithData:self.thumbnailData];
+    return nil;
+}
+
+//- (void)setThumbnailAttachmentId:(NSString *)thumbnailAttachmentId
+//{
+//     _thumbnailAttachmentId = thumbnailAttachmentId;
+//}
+//
+//- (BOOL)hasThumbnailAttachment
+//{
+//    return self.thumbnailAttachmentId.length > 0;
+//}
+//
 
-    // PERF TODO cache
-    return [UIImage imageWithData:self.thumbnailData];
+- (BOOL)hasThumbnailAttachments
+{
+    return self.thumbnailAttachmentIds.count > 0;
 }
 
+- (nullable TSAttachment *)firstThumbnailAttachmentWithTransaction:(YapDatabaseReadTransaction *)transaction;
+{
+    if (!self.hasThumbnailAttachments) {
+        return nil;
+    }
+    
+    return [TSAttachment fetchObjectWithUniqueID:self.thumbnailAttachmentIds.firstObject transaction:transaction];
+}
 
 @end
 

SignalServiceKit/src/Messages/OWSMessageSender.h

@@ -32,15 +32,6 @@ typedef void (^RetryableFailureHandler)(NSError *_Nonnull error);
 //
 // For example, If one member of a group deletes their account, the group should
 // ignore errors when trying to send messages to this ex-member.
-@interface NSError (OWSMessageSender)
-
-- (BOOL)isRetryable;
-- (void)setIsRetryable:(BOOL)value;
-
-- (BOOL)shouldBeIgnoredForGroups;
-- (void)setShouldBeIgnoredForGroups:(BOOL)value;
-
-@end
 
 #pragma mark -
 

SignalServiceKit/src/Messages/OWSMessageSender.m

@@ -5,8 +5,12 @@
 #import "OWSMessageSender.h"
 #import "AppContext.h"
 #import "ContactsUpdater.h"
+#import "Cryptography.h"
+#import "MIMETypeUtil.h"
 #import "NSData+keyVersionByte.h"
 #import "NSData+messagePadding.h"
+#import "NSError+MessageSending.h"
+#import "NSNotificationCenter+OWS.h"
 #import "OWSBackgroundTask.h"
 #import "OWSBlockingManager.h"
 #import "OWSDevice.h"
@@ -14,6 +18,7 @@
 #import "OWSError.h"
 #import "OWSIdentityManager.h"
 #import "OWSMessageServiceParams.h"
+#import "OWSOperation.h"
 #import "OWSOutgoingSentMessageTranscript.h"
 #import "OWSOutgoingSyncMessage.h"
 #import "OWSPrimaryStorage+PreKeyStore.h"
@@ -21,7 +26,7 @@
 #import "OWSPrimaryStorage+sessionStore.h"
 #import "OWSPrimaryStorage.h"
 #import "OWSRequestFactory.h"
-#import "OWSUploadingService.h"
+#import "OWSUploadOperation.h"
 #import "PreKeyBundle+jsonDict.h"
 #import "SignalRecipient.h"
 #import "TSAccountManager.h"
@@ -34,7 +39,9 @@
 #import "TSNetworkManager.h"
 #import "TSOutgoingMessage.h"
 #import "TSPreKeyManager.h"
+#import "TSQuotedMessage.h"
 #import "TSThread.h"
+#import "TextSecureKitEnv.h"
 #import "Threading.h"
 #import <AxolotlKit/AxolotlExceptions.h>
 #import <AxolotlKit/CipherMessage.h>
@@ -42,7 +49,6 @@
 #import <AxolotlKit/SessionBuilder.h>
 #import <AxolotlKit/SessionCipher.h>
 #import <TwistedOakCollapsingFutures/CollapsingFutures.h>
-#import <objc/runtime.h>
 
 NS_ASSUME_NONNULL_BEGIN
 
@@ -57,58 +63,6 @@ void AssertIsOnSendingQueue()
 #endif
 }
 
-static void *kNSError_MessageSender_IsRetryable = &kNSError_MessageSender_IsRetryable;
-static void *kNSError_MessageSender_ShouldBeIgnoredForGroups = &kNSError_MessageSender_ShouldBeIgnoredForGroups;
-static void *kNSError_MessageSender_IsFatal = &kNSError_MessageSender_IsFatal;
-
-// isRetryable and isFatal are opposites but not redundant.
-//
-// If a group message send fails, the send will be retried if any of the errors were retryable UNLESS
-// any of the errors were fatal.  Fatal errors trump retryable errors.
-@implementation NSError (OWSMessageSender)
-
-- (BOOL)isRetryable
-{
-    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_IsRetryable);
-    // This value should always be set for all errors by the time OWSSendMessageOperation
-    // queries it's value.  If not, default to retrying in production.
-    OWSAssert(value);
-    return value ? [value boolValue] : YES;
-}
-
-- (void)setIsRetryable:(BOOL)value
-{
-    objc_setAssociatedObject(self, kNSError_MessageSender_IsRetryable, @(value), OBJC_ASSOCIATION_COPY);
-}
-
-- (BOOL)shouldBeIgnoredForGroups
-{
-    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_ShouldBeIgnoredForGroups);
-    // This value will NOT always be set for all errors by the time we query it's value.
-    // Default to NOT ignoring.
-    return value ? [value boolValue] : NO;
-}
-
-- (void)setShouldBeIgnoredForGroups:(BOOL)value
-{
-    objc_setAssociatedObject(self, kNSError_MessageSender_ShouldBeIgnoredForGroups, @(value), OBJC_ASSOCIATION_COPY);
-}
-
-- (BOOL)isFatal
-{
-    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_IsFatal);
-    // This value will NOT always be set for all errors by the time we query it's value.
-    // Default to NOT fatal.
-    return value ? [value boolValue] : NO;
-}
-
-- (void)setIsFatal:(BOOL)value
-{
-    objc_setAssociatedObject(self, kNSError_MessageSender_IsFatal, @(value), OBJC_ASSOCIATION_COPY);
-}
-
-@end
-
 #pragma mark -
 
 /**
@@ -118,27 +72,22 @@ static void *kNSError_MessageSender_IsFatal = &kNSError_MessageSender_IsFatal;
  * Used by `OWSMessageSender` to serialize message sending, ensuring that messages are emitted in the order they
  * were sent.
  */
-@interface OWSSendMessageOperation : NSOperation
+@interface OWSSendMessageOperation : OWSOperation
 
 - (instancetype)init NS_UNAVAILABLE;
 - (instancetype)initWithMessage:(TSOutgoingMessage *)message
                   messageSender:(OWSMessageSender *)messageSender
-                        success:(void (^)(void))successHandler
-                        failure:(void (^)(NSError *_Nonnull error))failureHandler NS_DESIGNATED_INITIALIZER;
+                   dbConnection:(YapDatabaseConnection *)dbConnection
+                        success:(void (^)(void))aSuccessHandler
+                        failure:(void (^)(NSError *_Nonnull error))aFailureHandler NS_DESIGNATED_INITIALIZER;
 
 @end
 
 #pragma mark -
 
-typedef NS_ENUM(NSInteger, OWSSendMessageOperationState) {
-    OWSSendMessageOperationStateNew,
-    OWSSendMessageOperationStateExecuting,
-    OWSSendMessageOperationStateFinished
-};
-
 @interface OWSMessageSender (OWSSendMessageOperation)
 
-- (void)attemptToSendMessage:(TSOutgoingMessage *)message
+- (void)sendMessageToService:(TSOutgoingMessage *)message
                      success:(void (^)(void))successHandler
                      failure:(RetryableFailureHandler)failureHandler;
 
@@ -146,19 +95,13 @@ typedef NS_ENUM(NSInteger, OWSSendMessageOperationState) {
 
 #pragma mark -
 
-NSString *const OWSSendMessageOperationKeyIsExecuting = @"isExecuting";
-NSString *const OWSSendMessageOperationKeyIsFinished = @"isFinished";
-
-NSUInteger const OWSSendMessageOperationMaxRetries = 4;
-
 @interface OWSSendMessageOperation ()
 
 @property (nonatomic, readonly) TSOutgoingMessage *message;
 @property (nonatomic, readonly) OWSMessageSender *messageSender;
+@property (nonatomic, readonly) YapDatabaseConnection *dbConnection;
 @property (nonatomic, readonly) void (^successHandler)(void);
 @property (nonatomic, readonly) void (^failureHandler)(NSError *_Nonnull error);
-@property (nonatomic) OWSSendMessageOperationState operationState;
-@property (nonatomic) OWSBackgroundTask *backgroundTask;
 
 @end
 
@@ -168,144 +111,98 @@ NSUInteger const OWSSendMessageOperationMaxRetries = 4;
 
 - (instancetype)initWithMessage:(TSOutgoingMessage *)message
                   messageSender:(OWSMessageSender *)messageSender
-                        success:(void (^)(void))aSuccessHandler
-                        failure:(void (^)(NSError *_Nonnull error))aFailureHandler
+                   dbConnection:(YapDatabaseConnection *)dbConnection
+                        success:(void (^)(void))successHandler
+                        failure:(void (^)(NSError *_Nonnull error))failureHandler
 {
     self = [super init];
     if (!self) {
         return self;
     }
 
-    _operationState = OWSSendMessageOperationStateNew;
-    self.backgroundTask = [OWSBackgroundTask backgroundTaskWithLabelStr:__PRETTY_FUNCTION__];
-
+    self.remainingRetries = 6;
     _message = message;
     _messageSender = messageSender;
-
-    __weak typeof(self) weakSelf = self;
-    _successHandler = ^{
-        typeof(self) strongSelf = weakSelf;
-        if (!strongSelf) {
-            OWSProdCFail([OWSAnalyticsEvents messageSenderErrorSendOperationDidNotComplete]);
-            return;
-        }
-
-        [message updateWithMessageState:TSOutgoingMessageStateSentToService];
-
-        aSuccessHandler();
-
-        [strongSelf markAsComplete];
-    };
-
-    _failureHandler = ^(NSError *_Nonnull error) {
-        typeof(self) strongSelf = weakSelf;
-        if (!strongSelf) {
-            OWSProdCFail([OWSAnalyticsEvents messageSenderErrorSendOperationDidNotComplete]);
-            return;
-        }
-
-        [strongSelf.message updateWithSendingError:error];
-
-        DDLogDebug(@"%@ failed with error.", strongSelf.logTag);
-        aFailureHandler(error);
-
-        [strongSelf markAsComplete];
-    };
+    _dbConnection = dbConnection;
+    _successHandler = successHandler;
+    _failureHandler = failureHandler;
 
     return self;
 }
 
-#pragma mark - NSOperation overrides
+#pragma mark - OWSOperation overrides
 
-- (BOOL)isExecuting
+- (nullable NSError *)checkForPreconditionError
 {
-    return self.operationState == OWSSendMessageOperationStateExecuting;
-}
+    for (NSOperation *dependency in self.dependencies) {
+        if (![dependency isKindOfClass:[OWSOperation class]]) {
+            NSString *errorDescription =
+                [NSString stringWithFormat:@"%@ unknown dependency: %@", self.logTag, dependency.class];
+            NSError *assertionError = OWSErrorMakeAssertionError(errorDescription);
+            return assertionError;
+        }
 
-- (BOOL)isFinished
-{
-    return self.operationState == OWSSendMessageOperationStateFinished;
-}
+        OWSOperation *upload = (OWSOperation *)dependency;
 
-- (void)start
-{
-    [self willChangeValueForKey:OWSSendMessageOperationKeyIsExecuting];
-    self.operationState = OWSSendMessageOperationStateExecuting;
-    [self didChangeValueForKey:OWSSendMessageOperationKeyIsExecuting];
-    [self main];
-}
+        // Cannot proceed if dependency failed - surface the dependency's error.
+        NSError *_Nullable dependencyError = upload.failingError;
+        if (dependencyError) {
+            return dependencyError;
+        }
+    }
 
-- (void)main
-{
-    [self tryWithRemainingRetries:OWSSendMessageOperationMaxRetries];
-}
+    // Sanity check preconditions
+    if (self.message.hasAttachments) {
+        [self.dbConnection readWithBlock:^(YapDatabaseReadTransaction *_Nonnull transaction) {
+            TSAttachmentStream *attachmentStream
+                = (TSAttachmentStream *)[self.message attachmentWithTransaction:transaction];
+            OWSAssert(attachmentStream);
+            OWSAssert([attachmentStream isKindOfClass:[TSAttachmentStream class]]);
+            OWSAssert(attachmentStream.serverId);
+            OWSAssert(attachmentStream.isUploaded);
+        }];
+    }
 
-#pragma mark - methods
+    return nil;
+}
 
-- (void)tryWithRemainingRetries:(NSUInteger)remainingRetries
+- (void)run
 {
     // If the message has been deleted, abort send.
     if (self.message.shouldBeSaved && ![TSOutgoingMessage fetchObjectWithUniqueID:self.message.uniqueId]) {
         DDLogInfo(@"%@ aborting message send; message deleted.", self.logTag);
         NSError *error = OWSErrorWithCodeDescription(
             OWSErrorCodeMessageDeletedBeforeSent, @"Message was deleted before it could be sent.");
-        self.failureHandler(error);
+        error.isFatal = YES;
+        [self reportError:error];
         return;
     }
 
-    // Use this flag to ensure a given operation only succeeds or fails once.
-    __block BOOL onceFlag = NO;
-    RetryableFailureHandler retryableFailureHandler = ^(NSError *_Nonnull error) {
-        DDLogInfo(@"%@ Sending failed. Remaining retries: %lu", self.logTag, (unsigned long)remainingRetries);
-
-        OWSAssert(!onceFlag);
-        onceFlag = YES;
-
-        if (![error isRetryable] || [error isFatal]) {
-            DDLogInfo(@"%@ Skipping retry due to terminal error.", self.logTag);
-            self.failureHandler(error);
-            return;
-        }
-
-        if (remainingRetries > 0) {
-            [self tryWithRemainingRetries:remainingRetries - 1];
-        } else {
-            DDLogWarn(@"%@ Too many failures. Giving up sending.", self.logTag);
-
-            self.failureHandler(error);
+    [self.messageSender sendMessageToService:self.message
+        success:^{
+            [self reportSuccess];
         }
-    };
-
-    [self.messageSender attemptToSendMessage:self.message
-                                     success:^{
-                                         OWSAssert(!onceFlag);
-                                         onceFlag = YES;
-
-                                         self.successHandler();
-                                     }
-                                     failure:retryableFailureHandler];
+        failure:^(NSError *error) {
+            [self reportError:error];
+        }];
 }
 
-- (void)markAsComplete
+- (void)didSucceed
 {
-    [self willChangeValueForKey:OWSSendMessageOperationKeyIsExecuting];
-    [self willChangeValueForKey:OWSSendMessageOperationKeyIsFinished];
-
-    // Ensure we call the success or failure handler exactly once.
-    @synchronized(self)
-    {
-        OWSAssert(self.operationState != OWSSendMessageOperationStateFinished);
-
-        self.operationState = OWSSendMessageOperationStateFinished;
-    }
+    [self.message updateWithMessageState:TSOutgoingMessageStateSentToService];
+    self.successHandler();
+}
 
-    [self didChangeValueForKey:OWSSendMessageOperationKeyIsExecuting];
-    [self didChangeValueForKey:OWSSendMessageOperationKeyIsFinished];
+- (void)didFailWithError:(NSError *)error
+{
+    [self.message updateWithSendingError:error];
+    
+    DDLogDebug(@"%@ failed with error: %@", self.logTag, error);
+    self.failureHandler(error);
 }
 
 @end
 
-
 int const OWSMessageSenderRetryAttempts = 3;
 NSString *const OWSMessageSenderInvalidDeviceException = @"InvalidDeviceException";
 NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
@@ -315,7 +212,6 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
 @property (nonatomic, readonly) TSNetworkManager *networkManager;
 @property (nonatomic, readonly) OWSPrimaryStorage *primaryStorage;
 @property (nonatomic, readonly) OWSBlockingManager *blockingManager;
-@property (nonatomic, readonly) OWSUploadingService *uploadingService;
 @property (nonatomic, readonly) YapDatabaseConnection *dbConnection;
 @property (nonatomic, readonly) id<ContactsManagerProtocol> contactsManager;
 @property (nonatomic, readonly) ContactsUpdater *contactsUpdater;
@@ -340,8 +236,6 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
     _contactsManager = contactsManager;
     _contactsUpdater = contactsUpdater;
     _sendingQueueMap = [NSMutableDictionary new];
-
-    _uploadingService = [[OWSUploadingService alloc] initWithNetworkManager:networkManager];
     _dbConnection = primaryStorage.newDatabaseConnection;
 
     OWSSingletonAssert();
@@ -361,10 +255,16 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
 {
     OWSAssert(message);
 
+
     NSString *kDefaultQueueKey = @"kDefaultQueueKey";
     NSString *queueKey = message.uniqueThreadId ?: kDefaultQueueKey;
     OWSAssert(queueKey.length > 0);
 
+    if ([kDefaultQueueKey isEqualToString:queueKey]) {
+        // when do we get here?
+        DDLogDebug(@"%@ using default message queue", self.logTag);
+    }
+
     @synchronized(self)
     {
         NSOperationQueue *sendingQueue = self.sendingQueueMap[queueKey];
@@ -409,64 +309,134 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
             [message updateWithMessageState:TSOutgoingMessageStateAttemptingOut transaction:transaction];
         }];
 
+        NSOperationQueue *sendingQueue = [self sendingQueueForMessage:message];
         OWSSendMessageOperation *sendMessageOperation =
             [[OWSSendMessageOperation alloc] initWithMessage:message
                                                messageSender:self
+                                                dbConnection:self.dbConnection
                                                      success:successHandler
                                                      failure:failureHandler];
-
-        dispatch_async(dispatch_get_global_queue(DISPATCH_QUEUE_PRIORITY_DEFAULT, 0), ^{
-            NSOperationQueue *sendingQueue = [self sendingQueueForMessage:message];
-            [sendingQueue addOperation:sendMessageOperation];
-        });
-    });
-}
-
-- (void)attemptToSendMessage:(TSOutgoingMessage *)message
-                     success:(void (^)(void))successHandler
-                     failure:(RetryableFailureHandler)failureHandler
-{
-    [self ensureAnyAttachmentsUploaded:message
-        success:^() {
-            [self sendMessageToService:message
-                               success:successHandler
-                               failure:^(NSError *error) {
-                                   DDLogDebug(
-                                       @"%@ Message send attempt failed: %@", self.logTag, message.debugDescription);
-                                   failureHandler(error);
-                               }];
+        if (message.hasAttachments) {
+            OWSUploadOperation *uploadAttachmentOperation =
+                [[OWSUploadOperation alloc] initWithAttachmentId:message.attachmentIds.firstObject
+                                                         message:message
+                                                    dbConnection:self.dbConnection];
+            [sendMessageOperation addDependency:uploadAttachmentOperation];
+            [sendingQueue addOperation:uploadAttachmentOperation];
         }
-        failure:^(NSError *error) {
-            DDLogDebug(@"%@ Attachment upload attempt failed: %@", self.logTag, message.debugDescription);
-            failureHandler(error);
-        }];
-}
 
-- (void)ensureAnyAttachmentsUploaded:(TSOutgoingMessage *)message
-                             success:(void (^)(void))successHandler
-                             failure:(RetryableFailureHandler)failureHandler
-{
-    if (!message.hasAttachments) {
-        return successHandler();
-    }
-
-    TSAttachmentStream *attachmentStream =
-        [TSAttachmentStream fetchObjectWithUniqueID:message.attachmentIds.firstObject];
-
-    if (!attachmentStream) {
-        OWSProdError([OWSAnalyticsEvents messageSenderErrorCouldNotLoadAttachment]);
-        NSError *error = OWSErrorMakeFailedToSendOutgoingMessageError();
-        // Not finding local attachment is a terminal failure.
-        [error setIsRetryable:NO];
-        return failureHandler(error);
-    }
+        //        if (message.quotedMessage.hasThumbnailAttachments) {
+        //            OWSUploadOperation *uploadQuoteThumbnailOperation = [[OWSUploadOperation alloc]
+        //            initWithAttachmentId:message.attachmentIds.firstObject
+        //                                                                                                         message:message
+        //                                                                                                    dbConnection:self.dbConnection];
+        //            [sendMessageOperation addDependency:uploadAttachmentOperation];
+        //            [sendingQueue addOperation:uploadQuoteThumbnailOperation];
+        //        }
 
-    [self.uploadingService uploadAttachmentStream:attachmentStream
-                                          message:message
-                                          success:successHandler
-                                          failure:failureHandler];
+        [sendingQueue addOperation:sendMessageOperation];
+    });
 }
 
+//- (void)attemptToSendMessage:(TSOutgoingMessage *)message
+//                     success:(void (^)(void))successHandler
+//                     failure:(RetryableFailureHandler)failureHandler
+//{
+//    [self ensureAnyAttachmentsUploaded:message
+//        success:^() {
+//            [self sendMessageToService:message
+//                               success:successHandler
+//                               failure:^(NSError *error) {
+//                                   DDLogDebug(
+//                                       @"%@ Message send attempt failed: %@", self.logTag, message.debugDescription);
+//                                   failureHandler(error);
+//                               }];
+//        }
+//        failure:^(NSError *error) {
+//            DDLogDebug(@"%@ Attachment upload attempt failed: %@", self.logTag, message.debugDescription);
+//            failureHandler(error);
+//        }];
+//}
+//- (void)ensureAnyAttachmentsUploaded:(TSOutgoingMessage *)message
+//                             success:(void (^)(void))successHandler
+//                             failure:(RetryableFailureHandler)failureHandler
+//{
+//    if (!message.hasAttachments) {
+//        return successHandler();
+//    }
+//
+//    TSAttachmentStream *attachmentStream =
+//        [TSAttachmentStream fetchObjectWithUniqueID:message.attachmentIds.firstObject];
+//
+//    if (!attachmentStream) {
+//        OWSProdError([OWSAnalyticsEvents messageSenderErrorCouldNotLoadAttachment]);
+//        NSError *error = OWSErrorMakeFailedToSendOutgoingMessageError();
+//        // Not finding local attachment is a terminal failure.
+//        [error setIsRetryable:NO];
+//        return failureHandler(error);
+//    }
+//
+//    [OWSUploadingService uploadAttachmentStream:attachmentStream
+//                                        message:message
+//                                 networkManager:self.networkManager
+//                                        success:successHandler
+//                                        failure:failureHandler];
+//}
+
+//- (void)ensureAnyQuotedThumbnailUploaded:(TSOutgoingMessage *)message
+//                                 success:(void (^)(void))successHandler
+//                                 failure:(RetryableFailureHandler)failureHandler
+//{
+//    if (!message.hasAttachments) {
+//        return successHandler();
+//    }
+//
+//    TSAttachmentStream *attachmentStream =
+//    [TSAttachmentStream fetchObjectWithUniqueID:message.attachmentIds.firstObject];
+//
+//    if (!attachmentStream) {
+//        OWSProdError([OWSAnalyticsEvents messageSenderErrorCouldNotLoadAttachment]);
+//        NSError *error = OWSErrorMakeFailedToSendOutgoingMessageError();
+//        // Not finding local attachment is a terminal failure.
+//        [error setIsRetryable:NO];
+//        return failureHandler(error);
+//    }
+//
+//    if (message.quotedMessage.hasThumbnailAttachment) {
+//        DDLogDebug(@"%@ uploading thumbnail for message: %llu", self.logTag, message.timestamp);
+//
+//        __block TSAttachmentStream *thumbnailAttachmentStream;
+//        [self.dbConnection readWithBlock:^(YapDatabaseReadTransaction * _Nonnull transaction) {
+//            thumbnailAttachmentStream = [message.quotedMessage thumbnailAttachmentWithTransaction:transaction];
+//        }];
+//
+//        if (!thumbnailAttachmentStream) {
+//            OWSProdError([OWSAnalyticsEvents messageSenderErrorCouldNotLoadAttachment]);
+//            NSError *error = OWSErrorMakeFailedToSendOutgoingMessageError();
+//            // Not finding local attachment is a terminal failure.
+//            [error setIsRetryable:NO];
+//            return failureHandler(error);
+//        }
+//
+//        [self.uploadingService uploadAttachmentStream:attachmentStream
+//                                              message:message
+//                                              success:^() {
+//                                                  [self.uploadingService uploadAttachmentStream:attachmentStream
+//                                                                                        message:message
+//                                                                                        success:successHandler
+//                                                                                        failure:failureHandler];
+//                                              }
+//                                              failure:failureHandler];
+//
+//    }
+//    [self.uploadingService uploadAttachmentStream:attachmentStream
+//                                          message:message
+//                                          success:successHandler
+//                                          failure:failureHandler];
+//
+//
+//}
+
 - (void)enqueueTemporaryAttachment:(DataSource *)dataSource
                        contentType:(NSString *)contentType
                          inMessage:(TSOutgoingMessage *)message

SignalServiceKit/src/Network/API/OWSUploadOperation.h

@@ -0,0 +1,27 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+#import "OWSOperation.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+@class TSOutgoingMessage;
+@class YapDatabaseConnection;
+
+extern NSString *const kAttachmentUploadProgressNotification;
+extern NSString *const kAttachmentUploadProgressKey;
+extern NSString *const kAttachmentUploadAttachmentIDKey;
+
+@interface OWSUploadOperation : OWSOperation
+
+@property (nullable, readonly) NSError *lastError;
+
+- (instancetype)init NS_UNAVAILABLE;
+- (instancetype)initWithAttachmentId:(NSString *)attachmentId
+                             message:(TSOutgoingMessage *)outgoingMessage
+                        dbConnection:(YapDatabaseConnection *)dbConnection NS_DESIGNATED_INITIALIZER;
+
+@end
+
+NS_ASSUME_NONNULL_END

SignalServiceKit/src/Network/API/OWSUploadOperation.m

@@ -0,0 +1,190 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+#import "OWSUploadOperation.h"
+#import "Cryptography.h"
+#import "MIMETypeUtil.h"
+#import "NSError+MessageSending.h"
+#import "NSNotificationCenter+OWS.h"
+#import "OWSError.h"
+#import "OWSOperation.h"
+#import "OWSRequestFactory.h"
+#import "TSAttachmentStream.h"
+#import "TSNetworkManager.h"
+#import <YapDatabase/YapDatabaseConnection.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+NSString *const kAttachmentUploadProgressNotification = @"kAttachmentUploadProgressNotification";
+NSString *const kAttachmentUploadProgressKey = @"kAttachmentUploadProgressKey";
+NSString *const kAttachmentUploadAttachmentIDKey = @"kAttachmentUploadAttachmentIDKey";
+
+// Use a slightly non-zero value to ensure that the progress
+// indicator shows up as quickly as possible.
+static const CGFloat kAttachmentUploadProgressTheta = 0.001f;
+
+@interface OWSUploadOperation ()
+
+@property (readonly, nonatomic) NSString *attachmentId;
+@property (readonly, nonatomic) TSOutgoingMessage *outgoingMessage;
+@property (readonly, nonatomic) YapDatabaseConnection *dbConnection;
+
+@end
+
+@implementation OWSUploadOperation
+
+- (instancetype)initWithAttachmentId:(NSString *)attachmentId
+                             message:(TSOutgoingMessage *)outgoingMessage
+                        dbConnection:(YapDatabaseConnection *)dbConnection
+{
+    self = [super init];
+    if (!self) {
+        return self;
+    }
+
+    self.remainingRetries = 4;
+    _attachmentId = attachmentId;
+    _outgoingMessage = outgoingMessage;
+    _dbConnection = dbConnection;
+
+    return self;
+}
+
+- (TSNetworkManager *)networkManager
+{
+    return [TSNetworkManager sharedManager];
+}
+
+- (void)run
+{
+    __block TSAttachmentStream *attachmentStream;
+    [self.dbConnection readWithBlock:^(YapDatabaseReadTransaction *_Nonnull transaction) {
+        attachmentStream = [TSAttachmentStream fetchObjectWithUniqueID:self.attachmentId transaction:transaction];
+    }];
+
+    if (!attachmentStream) {
+        OWSProdError([OWSAnalyticsEvents messageSenderErrorCouldNotLoadAttachment]);
+        NSError *error = OWSErrorMakeFailedToSendOutgoingMessageError();
+        // Not finding local attachment is a terminal failure.
+        error.isRetryable = NO;
+        [self reportError:error];
+        return;
+    }
+
+    if (attachmentStream.isUploaded) {
+        DDLogDebug(@"%@ Attachment previously uploaded.", self.logTag);
+        [self reportSuccess];
+        return;
+    }
+    
+    [self fireNotificationWithProgress:0];
+
+    DDLogDebug(@"%@ alloc attachment: %@", self.logTag, self.attachmentId);
+    TSRequest *request = [OWSRequestFactory allocAttachmentRequest];
+    [self.networkManager makeRequest:request
+        success:^(NSURLSessionDataTask *task, id responseObject) {
+            if (![responseObject isKindOfClass:[NSDictionary class]]) {
+                DDLogError(@"%@ unexpected response from server: %@", self.logTag, responseObject);
+                NSError *error = OWSErrorMakeUnableToProcessServerResponseError();
+                error.isRetryable = YES;
+                [self reportError:error];
+                return;
+            }
+
+            NSDictionary *responseDict = (NSDictionary *)responseObject;
+            UInt64 serverId = ((NSDecimalNumber *)[responseDict objectForKey:@"id"]).unsignedLongLongValue;
+            NSString *location = [responseDict objectForKey:@"location"];
+
+            dispatch_async([OWSDispatch attachmentsQueue], ^{
+                [self uploadWithServerId:serverId location:location attachmentStream:attachmentStream];
+            });
+        }
+        failure:^(NSURLSessionDataTask *task, NSError *error) {
+            DDLogError(@"%@ Failed to allocate attachment with error: %@", self.logTag, error);
+            error.isRetryable = YES;
+            [self reportError:error];
+        }];
+}
+
+- (void)uploadWithServerId:(UInt64)serverId
+                  location:(NSString *)location
+          attachmentStream:(TSAttachmentStream *)attachmentStream
+{
+    DDLogDebug(@"%@ started uploading data for attachment: %@", self.logTag, self.attachmentId);
+    NSError *error;
+    NSData *attachmentData = [attachmentStream readDataFromFileWithError:&error];
+    if (error) {
+        DDLogError(@"%@ Failed to read attachment data with error: %@", self.logTag, error);
+        error.isRetryable = YES;
+        [self reportError:error];
+        return;
+    }
+
+    NSData *encryptionKey;
+    NSData *digest;
+    NSData *encryptedAttachmentData =
+        [Cryptography encryptAttachmentData:attachmentData outKey:&encryptionKey outDigest:&digest];
+
+    attachmentStream.encryptionKey = encryptionKey;
+    attachmentStream.digest = digest;
+
+    NSMutableURLRequest *request = [[NSMutableURLRequest alloc] initWithURL:[NSURL URLWithString:location]];
+    request.HTTPMethod = @"PUT";
+    [request setValue:OWSMimeTypeApplicationOctetStream forHTTPHeaderField:@"Content-Type"];
+
+    AFURLSessionManager *manager = [[AFURLSessionManager alloc]
+        initWithSessionConfiguration:[NSURLSessionConfiguration defaultSessionConfiguration]];
+
+    NSURLSessionUploadTask *uploadTask;
+    uploadTask = [manager uploadTaskWithRequest:request
+        fromData:encryptedAttachmentData
+        progress:^(NSProgress *_Nonnull uploadProgress) {
+            [self fireNotificationWithProgress:uploadProgress.fractionCompleted];
+        }
+        completionHandler:^(NSURLResponse *_Nonnull response, id _Nullable responseObject, NSError *_Nullable error) {
+            OWSAssertIsOnMainThread();
+            if (error) {
+                error.isRetryable = YES;
+                [self reportError:error];
+                return;
+            }
+
+            NSInteger statusCode = ((NSHTTPURLResponse *)response).statusCode;
+            BOOL isValidResponse = (statusCode >= 200) && (statusCode < 400);
+            if (!isValidResponse) {
+                DDLogError(@"%@ Unexpected server response: %d", self.logTag, (int)statusCode);
+                NSError *invalidResponseError = OWSErrorMakeUnableToProcessServerResponseError();
+                invalidResponseError.isRetryable = YES;
+                [self reportError:invalidResponseError];
+                return;
+            }
+
+            DDLogInfo(@"%@ Uploaded attachment: %p.", self.logTag, attachmentStream.uniqueId);
+            attachmentStream.serverId = serverId;
+            attachmentStream.isUploaded = YES;
+            [attachmentStream saveAsyncWithCompletionBlock:^{
+                [self reportSuccess];
+            }];
+        }];
+
+    [uploadTask resume];
+}
+
+- (void)fireNotificationWithProgress:(CGFloat)aProgress
+{
+    NSNotificationCenter *notificationCenter = [NSNotificationCenter defaultCenter];
+
+    CGFloat progress = MAX(kAttachmentUploadProgressTheta, aProgress);
+    [notificationCenter postNotificationNameAsync:kAttachmentUploadProgressNotification
+                                           object:nil
+                                         userInfo:@{
+                                             kAttachmentUploadProgressKey : @(progress),
+                                             kAttachmentUploadAttachmentIDKey : self.attachmentId
+                                         }];
+}
+
+
+@end
+
+NS_ASSUME_NONNULL_END

SignalServiceKit/src/Network/API/OWSUploadingService.h

@@ -1,29 +0,0 @@
-//
-//  Copyright (c) 2017 Open Whisper Systems. All rights reserved.
-//
-
-#import "OWSMessageSender.h"
-
-NS_ASSUME_NONNULL_BEGIN
-
-@class TSAttachmentStream;
-@class TSNetworkManager;
-@class TSOutgoingMessage;
-
-extern NSString *const kAttachmentUploadProgressNotification;
-extern NSString *const kAttachmentUploadProgressKey;
-extern NSString *const kAttachmentUploadAttachmentIDKey;
-
-@interface OWSUploadingService : NSObject
-
-- (instancetype)init NS_UNAVAILABLE;
-- (instancetype)initWithNetworkManager:(TSNetworkManager *)networkManager NS_DESIGNATED_INITIALIZER;
-
-- (void)uploadAttachmentStream:(TSAttachmentStream *)attachmentStream
-                       message:(TSOutgoingMessage *)outgoingMessage
-                       success:(void (^)(void))successHandler
-                       failure:(RetryableFailureHandler)failureHandler;
-
-@end
-
-NS_ASSUME_NONNULL_END

SignalServiceKit/src/Network/API/OWSUploadingService.m

@@ -1,181 +0,0 @@
-//
-//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
-//
-
-#import "OWSUploadingService.h"
-#import "Cryptography.h"
-#import "MIMETypeUtil.h"
-#import "NSNotificationCenter+OWS.h"
-#import "OWSError.h"
-#import "OWSMessageSender.h"
-#import "OWSRequestFactory.h"
-#import "TSAttachmentStream.h"
-#import "TSNetworkManager.h"
-#import "TSOutgoingMessage.h"
-
-NS_ASSUME_NONNULL_BEGIN
-
-NSString *const kAttachmentUploadProgressNotification = @"kAttachmentUploadProgressNotification";
-NSString *const kAttachmentUploadProgressKey = @"kAttachmentUploadProgressKey";
-NSString *const kAttachmentUploadAttachmentIDKey = @"kAttachmentUploadAttachmentIDKey";
-
-// Use a slightly non-zero value to ensure that the progress
-// indicator shows up as quickly as possible.
-static const CGFloat kAttachmentUploadProgressTheta = 0.001f;
-
-@interface OWSUploadingService ()
-
-@property (nonatomic, readonly) TSNetworkManager *networkManager;
-
-@end
-
-@implementation OWSUploadingService
-
-- (instancetype)initWithNetworkManager:(TSNetworkManager *)networkManager
-{
-    self = [super init];
-    if (!self) {
-        return self;
-    }
-
-    _networkManager = networkManager;
-
-    return self;
-}
-
-- (void)uploadAttachmentStream:(TSAttachmentStream *)attachmentStream
-                       message:(TSOutgoingMessage *)outgoingMessage
-                       success:(void (^)(void))successHandler
-                       failure:(RetryableFailureHandler)failureHandler
-{
-    void (^successHandlerWrapper)(void) = ^{
-        [self fireProgressNotification:1 attachmentId:attachmentStream.uniqueId];
-
-        successHandler();
-    };
-
-    RetryableFailureHandler failureHandlerWrapper = ^(NSError *_Nonnull error) {
-        [self fireProgressNotification:0 attachmentId:attachmentStream.uniqueId];
-
-        failureHandler(error);
-    };
-
-    if (attachmentStream.serverId) {
-        DDLogDebug(@"%@ Attachment previously uploaded.", self.logTag);
-        successHandlerWrapper();
-        return;
-    }
-
-    [self fireProgressNotification:kAttachmentUploadProgressTheta attachmentId:attachmentStream.uniqueId];
-
-    TSRequest *request = [OWSRequestFactory allocAttachmentRequest];
-    [self.networkManager makeRequest:request
-        success:^(NSURLSessionDataTask *task, id responseObject) {
-            dispatch_async([OWSDispatch attachmentsQueue], ^{ // TODO can we move this queue specification up a level?
-                if (![responseObject isKindOfClass:[NSDictionary class]]) {
-                    DDLogError(@"%@ unexpected response from server: %@", self.logTag, responseObject);
-                    NSError *error = OWSErrorMakeUnableToProcessServerResponseError();
-                    [error setIsRetryable:YES];
-                    return failureHandlerWrapper(error);
-                }
-
-                NSDictionary *responseDict = (NSDictionary *)responseObject;
-                UInt64 serverId = ((NSDecimalNumber *)[responseDict objectForKey:@"id"]).unsignedLongLongValue;
-                NSString *location = [responseDict objectForKey:@"location"];
-
-                NSError *error;
-                NSData *attachmentData = [attachmentStream readDataFromFileWithError:&error];
-                if (error) {
-                    DDLogError(@"%@ Failed to read attachment data with error:%@", self.logTag, error);
-                    [error setIsRetryable:YES];
-                    return failureHandlerWrapper(error);
-                }
-
-                NSData *encryptionKey;
-                NSData *digest;
-                NSData *encryptedAttachmentData =
-                    [Cryptography encryptAttachmentData:attachmentData outKey:&encryptionKey outDigest:&digest];
-
-                attachmentStream.encryptionKey = encryptionKey;
-                attachmentStream.digest = digest;
-
-                [self uploadDataWithProgress:encryptedAttachmentData
-                                    location:location
-                                attachmentId:attachmentStream.uniqueId
-                                     success:^{
-                                         OWSAssertIsOnMainThread();
-
-                                         DDLogInfo(@"%@ Uploaded attachment: %p.", self.logTag, attachmentStream);
-                                         attachmentStream.serverId = serverId;
-                                         attachmentStream.isUploaded = YES;
-                                         [attachmentStream saveAsyncWithCompletionBlock:successHandlerWrapper];
-                                     }
-                                     failure:failureHandlerWrapper];
-
-            });
-        }
-        failure:^(NSURLSessionDataTask *task, NSError *error) {
-            DDLogError(@"%@ Failed to allocate attachment with error: %@", self.logTag, error);
-            [error setIsRetryable:YES];
-            failureHandlerWrapper(error);
-        }];
-}
-
-
-- (void)uploadDataWithProgress:(NSData *)cipherText
-                      location:(NSString *)location
-                  attachmentId:(NSString *)attachmentId
-                       success:(void (^)(void))successHandler
-                       failure:(RetryableFailureHandler)failureHandler
-{
-    NSMutableURLRequest *request = [[NSMutableURLRequest alloc] initWithURL:[NSURL URLWithString:location]];
-    request.HTTPMethod = @"PUT";
-    request.HTTPBody = cipherText;
-    [request setValue:OWSMimeTypeApplicationOctetStream forHTTPHeaderField:@"Content-Type"];
-
-    AFURLSessionManager *manager = [[AFURLSessionManager alloc]
-        initWithSessionConfiguration:[NSURLSessionConfiguration defaultSessionConfiguration]];
-
-    NSURLSessionUploadTask *uploadTask;
-    uploadTask = [manager uploadTaskWithRequest:request
-        fromData:cipherText
-        progress:^(NSProgress *_Nonnull uploadProgress) {
-            [self fireProgressNotification:MAX(kAttachmentUploadProgressTheta, uploadProgress.fractionCompleted)
-                              attachmentId:attachmentId];
-        }
-        completionHandler:^(NSURLResponse *_Nonnull response, id _Nullable responseObject, NSError *_Nullable error) {
-            OWSAssertIsOnMainThread();
-            if (error) {
-                [error setIsRetryable:YES];
-                return failureHandler(error);
-            }
-
-            NSInteger statusCode = ((NSHTTPURLResponse *)response).statusCode;
-            BOOL isValidResponse = (statusCode >= 200) && (statusCode < 400);
-            if (!isValidResponse) {
-                DDLogError(@"%@ Unexpected server response: %d", self.logTag, (int)statusCode);
-                NSError *invalidResponseError = OWSErrorMakeUnableToProcessServerResponseError();
-                [invalidResponseError setIsRetryable:YES];
-                return failureHandler(invalidResponseError);
-            }
-
-            successHandler();
-        }];
-
-    [uploadTask resume];
-}
-
-- (void)fireProgressNotification:(CGFloat)progress attachmentId:(NSString *)attachmentId
-{
-    NSNotificationCenter *notificationCenter = [NSNotificationCenter defaultCenter];
-    [notificationCenter postNotificationNameAsync:kAttachmentUploadProgressNotification
-                                           object:nil
-                                         userInfo:@{
-                                             kAttachmentUploadProgressKey : @(progress),
-                                             kAttachmentUploadAttachmentIDKey : attachmentId
-                                         }];
-}
-
-@end
-
-NS_ASSUME_NONNULL_END

SignalServiceKit/src/Network/OWSCensorshipConfiguration.m

@@ -169,16 +169,17 @@ NSString *const OWSCensorshipConfiguration_DefaultFrontingHost = OWSCensorshipCo
 + (nullable NSData *)certificateDataWithName:(NSString *)name error:(NSError **)error
 {
     if (!name.length) {
-        OWSFail(@"%@ expected name with length > 0", self.logTag);
-        *error = OWSErrorMakeAssertionError();
+        NSString *failureDescription = [NSString stringWithFormat:@"%@ expected name with length > 0", self.logTag];
+        *error = OWSErrorMakeAssertionError(failureDescription);
         return nil;
     }
 
     NSBundle *bundle = [NSBundle bundleForClass:self.class];
     NSString *path = [bundle pathForResource:name ofType:@"crt"];
     if (![[NSFileManager defaultManager] fileExistsAtPath:path]) {
-        OWSFail(@"%@ Missing certificate for name: %@", self.logTag, name);
-        *error = OWSErrorMakeAssertionError();
+        NSString *failureDescription =
+            [NSString stringWithFormat:@"%@ Missing certificate for name: %@", self.logTag, name];
+        *error = OWSErrorMakeAssertionError(failureDescription);
         return nil;
     }
 

SignalServiceKit/src/Util/NSError+MessageSending.h

@@ -0,0 +1,15 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+NS_ASSUME_NONNULL_BEGIN
+
+@interface NSError (MessageSending)
+
+@property (nonatomic) BOOL isRetryable;
+@property (nonatomic) BOOL isFatal;
+@property (nonatomic) BOOL shouldBeIgnoredForGroups;
+
+@end
+
+NS_ASSUME_NONNULL_END

SignalServiceKit/src/Util/NSError+MessageSending.m

@@ -0,0 +1,62 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+#import "NSError+MessageSending.h"
+#import <objc/runtime.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+static void *kNSError_MessageSender_IsRetryable = &kNSError_MessageSender_IsRetryable;
+static void *kNSError_MessageSender_ShouldBeIgnoredForGroups = &kNSError_MessageSender_ShouldBeIgnoredForGroups;
+static void *kNSError_MessageSender_IsFatal = &kNSError_MessageSender_IsFatal;
+
+// isRetryable and isFatal are opposites but not redundant.
+//
+// If a group message send fails, the send will be retried if any of the errors were retryable UNLESS
+// any of the errors were fatal.  Fatal errors trump retryable errors.
+@implementation NSError (MessageSending)
+
+- (BOOL)isRetryable
+{
+    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_IsRetryable);
+    // This value should always be set for all errors by the time OWSSendMessageOperation
+    // queries it's value.  If not, default to retrying in production.
+    OWSAssert(value);
+    return value ? [value boolValue] : YES;
+}
+
+- (void)setIsRetryable:(BOOL)value
+{
+    objc_setAssociatedObject(self, kNSError_MessageSender_IsRetryable, @(value), OBJC_ASSOCIATION_COPY);
+}
+
+- (BOOL)shouldBeIgnoredForGroups
+{
+    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_ShouldBeIgnoredForGroups);
+    // This value will NOT always be set for all errors by the time we query it's value.
+    // Default to NOT ignoring.
+    return value ? [value boolValue] : NO;
+}
+
+- (void)setShouldBeIgnoredForGroups:(BOOL)value
+{
+    objc_setAssociatedObject(self, kNSError_MessageSender_ShouldBeIgnoredForGroups, @(value), OBJC_ASSOCIATION_COPY);
+}
+
+- (BOOL)isFatal
+{
+    NSNumber *value = objc_getAssociatedObject(self, kNSError_MessageSender_IsFatal);
+    // This value will NOT always be set for all errors by the time we query it's value.
+    // Default to NOT fatal.
+    return value ? [value boolValue] : NO;
+}
+
+- (void)setIsFatal:(BOOL)value
+{
+    objc_setAssociatedObject(self, kNSError_MessageSender_IsFatal, @(value), OBJC_ASSOCIATION_COPY);
+}
+
+@end
+
+NS_ASSUME_NONNULL_END

SignalServiceKit/src/Util/OWSError.h

@@ -15,6 +15,7 @@ typedef NS_ENUM(NSInteger, OWSErrorCode) {
     OWSErrorCodePrivacyVerificationFailure = 20,
     OWSErrorCodeUntrustedIdentity = 25,
     OWSErrorCodeFailedToSendOutgoingMessage = 30,
+    OWSErrorCodeAssertionFailure = 31,
     OWSErrorCodeFailedToDecryptMessage = 100,
     OWSErrorCodeFailedToEncryptMessage = 110,
     OWSErrorCodeSignalServiceFailure = 1001,
@@ -51,7 +52,7 @@ extern NSError *OWSErrorMakeUntrustedIdentityError(NSString *description, NSStri
 extern NSError *OWSErrorMakeUnableToProcessServerResponseError(void);
 extern NSError *OWSErrorMakeFailedToSendOutgoingMessageError(void);
 extern NSError *OWSErrorMakeNoSuchSignalRecipientError(void);
-extern NSError *OWSErrorMakeAssertionError(void);
+extern NSError *OWSErrorMakeAssertionError(NSString *description);
 extern NSError *OWSErrorMakeMessageSendDisabledDueToPreKeyUpdateFailuresError(void);
 extern NSError *OWSErrorMakeMessageSendFailedToBlockListError(void);
 extern NSError *OWSErrorMakeWriteAttachmentDataError(void);

SignalServiceKit/src/Util/OWSError.m

@@ -35,10 +35,11 @@ NSError *OWSErrorMakeNoSuchSignalRecipientError()
             @"ERROR_DESCRIPTION_UNREGISTERED_RECIPIENT", @"Error message when attempting to send message"));
 }
 
-NSError *OWSErrorMakeAssertionError()
+NSError *OWSErrorMakeAssertionError(NSString *description)
 {
-    return OWSErrorWithCodeDescription(OWSErrorCodeFailedToSendOutgoingMessage,
-                                       NSLocalizedString(@"ERROR_DESCRIPTION_UNKNOWN_ERROR", @"Worst case generic error message"));
+    OWSCFail(@"Assertion failed: %@", description);
+    return OWSErrorWithCodeDescription(OWSErrorCodeAssertionFailure,
+        NSLocalizedString(@"ERROR_DESCRIPTION_UNKNOWN_ERROR", @"Worst case generic error message"));
 }
 
 NSError *OWSErrorMakeUntrustedIdentityError(NSString *description, NSString *recipientId)

SignalServiceKit/src/Util/OWSOperation.h

@@ -0,0 +1,63 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+#import <Foundation/Foundation.h>
+
+NS_ASSUME_NONNULL_BEGIN
+
+typedef NS_ENUM(NSInteger, OWSOperationState) {
+    OWSOperationStateNew,
+    OWSOperationStateExecuting,
+    OWSOperationStateFinished
+};
+
+// A base class for implementing retryable operations.
+// To utilize the retryable behavior:
+// Set remainingRetries to something greater than 0, and when you're reporting an error,
+// set `error.isRetryable = YES`.
+// If the failure is one that will not succeed upon retry, set `error.isFatal = YES`.
+//
+// isRetryable and isFatal are opposites but not redundant.
+//
+// If a group message send fails, the send will be retried if any of the errors were retryable UNLESS
+// any of the errors were fatal. Fatal errors trump retryable errors.
+@interface OWSOperation : NSOperation
+
+@property (nullable) NSError *failingError;
+@property NSUInteger remainingRetries;
+
+#pragma mark - Subclass Overrides
+
+// Called one time only
+- (nullable NSError *)checkForPreconditionError;
+
+// Called every retry, this is where the bulk of the operation's work should go.
+- (void)run;
+
+// Called at most one time.
+- (void)didSucceed;
+
+// Called at most one time, once retry is no longer possible.
+- (void)didFailWithError:(NSError *)error;
+
+#pragma mark - Success/Error - Do Not Override
+
+// Complete the operation successfully.
+// Should be called at most once per operation instance.
+- (void)reportSuccess;
+
+// To avoid retry, report an error with `error.isFatal = YES`
+// otherwise the operation will retry if possible.
+// Should be called at most once per `run`, and you should
+// ensure that `run` cannot succeed after calling `reportError`
+// e.g. generally:
+//
+//     [self reportError:someError];
+//     return;
+//
+- (void)reportError:(NSError *)error;
+
+@end
+
+NS_ASSUME_NONNULL_END

SignalServiceKit/src/Util/OWSOperation.m

@@ -0,0 +1,181 @@
+//
+//  Copyright (c) 2018 Open Whisper Systems. All rights reserved.
+//
+
+#import "OWSOperation.h"
+#import "NSError+MessageSending.h"
+#import "OWSBackgroundTask.h"
+
+NS_ASSUME_NONNULL_BEGIN
+
+NSString *const OWSOperationKeyIsExecuting = @"isExecuting";
+NSString *const OWSOperationKeyIsFinished = @"isFinished";
+
+@interface OWSOperation ()
+
+@property (nonatomic) OWSOperationState operationState;
+@property (nonatomic) OWSBackgroundTask *backgroundTask;
+
+@end
+
+@implementation OWSOperation
+
+- (instancetype)init
+{
+    self = [super init];
+    if (!self) {
+        return self;
+    }
+
+    _operationState = OWSOperationStateNew;
+    _backgroundTask = [OWSBackgroundTask backgroundTaskWithLabel:self.logTag];
+    
+    // Operations are not retryable by default.
+    _remainingRetries = 0;
+
+    return self;
+}
+
+- (void)dealloc
+{
+    DDLogDebug(@"%@ in dealloc", self.logTag);
+}
+
+#pragma mark - Subclass Overrides
+
+// Called one time only
+- (nullable NSError *)checkForPreconditionError
+{
+    // no-op
+    // Override in subclass if necessary
+    return nil;
+}
+
+// Called every retry, this is where the bulk of the operation's work should go.
+- (void)run
+{
+    OWSFail(@"%@ Abstract method", self.logTag);
+}
+
+// Called at most one time.
+- (void)didSucceed
+{
+    // no-op
+    // Override in subclass if necessary
+}
+
+// Called at most one time, once retry is no longer possible.
+- (void)didFailWithError:(NSError *)error
+{
+    // no-op
+    // Override in subclass if necessary
+}
+
+#pragma mark - NSOperation overrides
+
+// Do not override this method in a subclass instead, override `run`
+- (void)main
+{
+    DDLogDebug(@"%@ started.", self.logTag);
+    NSError *_Nullable preconditionError = [self checkForPreconditionError];
+    if (preconditionError) {
+        [self failOperationWithError:preconditionError];
+        return;
+    }
+
+    [self run];
+}
+
+#pragma mark - Public Methods
+
+// These methods are not intended to be subclassed
+- (void)reportSuccess
+{
+    DDLogDebug(@"%@ succeeded.", self.logTag);
+    [self didSucceed];
+    [self markAsComplete];
+}
+
+- (void)reportError:(NSError *)error
+{
+    DDLogDebug(@"%@ reportError: %@, fatal?: %d, retryable?: %d, remainingRetries: %d",
+        self.logTag,
+        error,
+        error.isFatal,
+        error.isRetryable,
+        self.remainingRetries);
+
+    if (error.isFatal) {
+        [self failOperationWithError:error];
+        return;
+    }
+
+    if (!error.isRetryable) {
+        [self failOperationWithError:error];
+        return;
+    }
+
+    if (self.remainingRetries == 0) {
+        [self failOperationWithError:error];
+        return;
+    }
+
+    self.remainingRetries--;
+
+    // TODO Do we want some kind of exponential backoff?
+    // I'm not sure that there is a one-size-fits all backoff approach
+    dispatch_after(dispatch_time(DISPATCH_TIME_NOW, (int64_t)(0.1 * NSEC_PER_SEC)), dispatch_get_main_queue(), ^{
+        [self run];
+    });
+}
+
+#pragma mark - Life Cycle
+
+- (void)failOperationWithError:(NSError *)error
+{
+    DDLogDebug(@"%@ failed terminally.", self.logTag);
+    self.failingError = error;
+
+    [self didFailWithError:error];
+    [self markAsComplete];
+}
+
+- (BOOL)isExecuting
+{
+    return self.operationState == OWSOperationStateExecuting;
+}
+
+- (BOOL)isFinished
+{
+    return self.operationState == OWSOperationStateFinished;
+}
+
+- (void)start
+{
+    [self willChangeValueForKey:OWSOperationKeyIsExecuting];
+    self.operationState = OWSOperationStateExecuting;
+    [self didChangeValueForKey:OWSOperationKeyIsExecuting];
+
+    [self main];
+}
+
+- (void)markAsComplete
+{
+    [self willChangeValueForKey:OWSOperationKeyIsExecuting];
+    [self willChangeValueForKey:OWSOperationKeyIsFinished];
+
+    // Ensure we call the success or failure handler exactly once.
+    @synchronized(self)
+    {
+        OWSAssert(self.operationState != OWSOperationStateFinished);
+
+        self.operationState = OWSOperationStateFinished;
+    }
+
+    [self didChangeValueForKey:OWSOperationKeyIsExecuting];
+    [self didChangeValueForKey:OWSOperationKeyIsFinished];
+}
+
+@end
+
+NS_ASSUME_NONNULL_END