diff --git a/Signal/src/ViewControllers/DebugUI/DebugUIMessages.m b/Signal/src/ViewControllers/DebugUI/DebugUIMessages.m
index ebab8c895..f82105167 100644
--- a/Signal/src/ViewControllers/DebugUI/DebugUIMessages.m
+++ b/Signal/src/ViewControllers/DebugUI/DebugUIMessages.m
@@ -127,6 +127,10 @@ NS_ASSUME_NONNULL_BEGIN
                         actionBlock:^{
                             [DebugUIMessages sendNTextMessagesInThread:thread];
                         }],
+        [OWSTableItem itemWithTitle:@"Send multi-image messages"
+                        actionBlock:^{
+                            [DebugUIMessages sendMultiImageMessageInThread:thread];
+                        }],
         [OWSTableItem itemWithTitle:@"Select Fake"
                         actionBlock:^{
                             [DebugUIMessages selectFakeAction:thread];
@@ -246,7 +250,6 @@ NS_ASSUME_NONNULL_BEGIN
                   [self.dbConnection readWriteWithBlock:^(YapDatabaseReadWriteTransaction *_Nonnull transaction) {
                       [self.messageSenderJobQueue addMessage:syncGroupsRequestMessage transaction:transaction];
                   }];
-                  
               }],
         [OWSTableItem itemWithTitle:@"Message with stalled timer"
                         actionBlock:^{
@@ -3357,7 +3360,7 @@ typedef OWSContact * (^OWSContactBlock)(YapDatabaseReadWriteTransaction *transac
         // style them indistinguishably from a separate text message.
         attachment.captionText = [self randomCaptionText];
     }
-    [ThreadUtil enqueueMessageWithAttachment:attachment inThread:thread quotedReplyModel:nil ignoreErrors:YES];
+    [ThreadUtil enqueueMessageWithAttachment:attachment inThread:thread quotedReplyModel:nil];
 }
 
 + (SSKProtoEnvelope *)createEnvelopeForThread:(TSThread *)thread
@@ -4631,6 +4634,41 @@ typedef OWSContact * (^OWSContactBlock)(YapDatabaseReadWriteTransaction *transac
     }
 }
 
++ (void)sendMultiImageMessageInThread:(TSThread *)thread
+{
+    OWSLogInfo(@"");
+
+    const uint32_t kMinImageCount = 2;
+    const uint32_t kMaxImageCount = 10;
+    uint32_t imageCount = kMinImageCount + arc4random_uniform(kMaxImageCount - kMinImageCount);
+
+    NSMutableArray<SignalAttachment *> *attachments = [NSMutableArray new];
+    for (uint32_t i = 0; i < imageCount; i++) {
+        UIColor *imageColor = [UIColor colorWithRed:arc4random_uniform(256) / 255.f
+                                              green:arc4random_uniform(256) / 255.f
+                                               blue:arc4random_uniform(256) / 255.f
+                                              alpha:1.f];
+        UIImage *image = [UIImage imageWithColor:imageColor size:CGSizeMake(10.f, 10.f)];
+        OWSAssertDebug(image);
+        NSData *pngData = UIImagePNGRepresentation(image);
+        OWSAssertDebug(pngData);
+        NSString *filePath = [OWSFileSystem temporaryFilePathWithFileExtension:@"png"];
+        [pngData writeToFile:filePath atomically:YES];
+        OWSAssertDebug([NSFileManager.defaultManager fileExistsAtPath:filePath]);
+        DataSource *dataSource = [DataSourcePath dataSourceWithFilePath:filePath shouldDeleteOnDeallocation:YES];
+        SignalAttachment *attachment = [SignalAttachment attachmentWithDataSource:dataSource
+                                                                          dataUTI:(NSString *)kUTTypePNG
+                                                                     imageQuality:TSImageQualityOriginal];
+        [attachments addObject:attachment];
+    }
+
+    [self.dbConnection readWriteWithBlock:^(YapDatabaseReadWriteTransaction *transaction) {
+        TSOutgoingMessage *message =
+            [ThreadUtil enqueueMessageWithAttachments:attachments inThread:thread quotedReplyModel:nil];
+        OWSLogError(@"timestamp: %llu.", message.timestamp);
+    }];
+}
+
 #endif
 
 @end
diff --git a/SignalMessaging/utils/ThreadUtil.h b/SignalMessaging/utils/ThreadUtil.h
index e882e98a1..1afec1ba7 100644
--- a/SignalMessaging/utils/ThreadUtil.h
+++ b/SignalMessaging/utils/ThreadUtil.h
@@ -53,10 +53,9 @@ NS_ASSUME_NONNULL_BEGIN
                                            inThread:(TSThread *)thread
                                    quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel;
 
-+ (TSOutgoingMessage *)enqueueMessageWithAttachment:(SignalAttachment *)attachment
-                                           inThread:(TSThread *)thread
-                                   quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel
-                                       ignoreErrors:(BOOL)ignoreErrors;
++ (TSOutgoingMessage *)enqueueMessageWithAttachments:(NSArray<SignalAttachment *> *)attachments
+                                            inThread:(TSThread *)thread
+                                    quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel;
 
 + (TSOutgoingMessage *)enqueueMessageWithContactShare:(OWSContact *)contactShare inThread:(TSThread *)thread;
 + (void)enqueueLeaveGroupMessageInThread:(TSGroupThread *)thread;
diff --git a/SignalMessaging/utils/ThreadUtil.m b/SignalMessaging/utils/ThreadUtil.m
index 87174ff80..51d78d3e5 100644
--- a/SignalMessaging/utils/ThreadUtil.m
+++ b/SignalMessaging/utils/ThreadUtil.m
@@ -93,35 +93,36 @@ NS_ASSUME_NONNULL_BEGIN
                                            inThread:(TSThread *)thread
                                    quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel
 {
-    return [self enqueueMessageWithAttachment:attachment
-                                     inThread:thread
-                             quotedReplyModel:quotedReplyModel
-                                 ignoreErrors:NO];
+    return [self enqueueMessageWithAttachment:attachment inThread:thread quotedReplyModel:quotedReplyModel];
 }
 
-+ (TSOutgoingMessage *)enqueueMessageWithAttachment:(SignalAttachment *)attachment
-                                           inThread:(TSThread *)thread
-                                   quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel
-                                       ignoreErrors:(BOOL)ignoreErrors
++ (TSOutgoingMessage *)enqueueMessageWithAttachments:(NSArray<SignalAttachment *> *)attachments
+                                            inThread:(TSThread *)thread
+                                    quotedReplyModel:(nullable OWSQuotedReplyModel *)quotedReplyModel
 {
     OWSAssertIsOnMainThread();
-    OWSAssertDebug(attachment);
-    OWSAssertDebug(!attachment.hasError);
-    OWSAssertDebug(attachment.mimeType.length > 0);
+    OWSAssertDebug(attachments.count > 0);
     OWSAssertDebug(thread);
+    for (SignalAttachment *attachment in attachments) {
+        OWSAssertDebug(!attachment.hasError);
+        OWSAssertDebug(attachment.mimeType.length > 0);
+    }
 
     OWSDisappearingMessagesConfiguration *configuration =
         [OWSDisappearingMessagesConfiguration fetchObjectWithUniqueID:thread.uniqueId];
 
     uint32_t expiresInSeconds = (configuration.isEnabled ? configuration.durationSeconds : 0);
+    BOOL isVoiceMessage = (attachments.count == 1 && attachments.lastObject.isVoiceMessage);
+    // TODO: Support multi-image captions.
+    NSString *_Nullable messageBody = attachments.lastObject.captionText;
     TSOutgoingMessage *message =
         [[TSOutgoingMessage alloc] initOutgoingMessageWithTimestamp:[NSDate ows_millisecondTimeStamp]
                                                            inThread:thread
-                                                        messageBody:attachment.captionText
+                                                        messageBody:messageBody
                                                       attachmentIds:[NSMutableArray new]
                                                    expiresInSeconds:expiresInSeconds
                                                     expireStartedAt:0
-                                                     isVoiceMessage:[attachment isVoiceMessage]
+                                                     isVoiceMessage:isVoiceMessage
                                                    groupMetaMessage:TSGroupMetaMessageUnspecified
                                                       quotedMessage:[quotedReplyModel buildQuotedMessageForSending]
                                                        contactShare:nil];