diff --git a/SignalServiceKit/src/Messages/DeviceSyncing/OWSOutgoingSentMessageTranscript.m b/SignalServiceKit/src/Messages/DeviceSyncing/OWSOutgoingSentMessageTranscript.m
index c3dfee8f5..e19f5bea3 100644
--- a/SignalServiceKit/src/Messages/DeviceSyncing/OWSOutgoingSentMessageTranscript.m
+++ b/SignalServiceKit/src/Messages/DeviceSyncing/OWSOutgoingSentMessageTranscript.m
@@ -67,7 +67,7 @@ NS_ASSUME_NONNULL_BEGIN
     [sentBuilder setMessage:dataMessage];
     [sentBuilder setExpirationStartTimestamp:self.message.timestamp];
 
-    for (NSString *recipientId in self.message.recipientIds) {
+    for (NSString *recipientId in self.message.sentRecipientIds) {
         TSOutgoingMessageRecipientState *_Nullable recipientState =
             [self.message recipientStateForRecipientId:recipientId];
         if (!recipientState) {
@@ -75,6 +75,7 @@ NS_ASSUME_NONNULL_BEGIN
             continue;
         }
         if (recipientState.state != OWSOutgoingMessageRecipientStateSent) {
+            OWSFailDebug(@"unexpected recipient state for: %@", recipientId);
             continue;
         }
 
diff --git a/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.h b/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.h
index 7c73bf122..d3b00bbe2 100644
--- a/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.h
+++ b/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.h
@@ -113,6 +113,7 @@ typedef NS_ENUM(NSInteger, TSGroupMetaMessage) {
 
 @property (readonly) TSOutgoingMessageState messageState;
 @property (readonly) BOOL wasDeliveredToAnyRecipient;
+@property (readonly) BOOL wasSentToAnyRecipient;
 
 @property (atomic, readonly) BOOL hasSyncedTranscript;
 @property (atomic, readonly) NSString *customMessage;
@@ -155,7 +156,10 @@ typedef NS_ENUM(NSInteger, TSGroupMetaMessage) {
 // All recipients of this message who we are currently trying to send to (queued, uploading or during send).
 - (NSArray<NSString *> *)sendingRecipientIds;
 
-// All recipients of this message to whom it has been sent and delivered.
+// All recipients of this message to whom it has been sent (and possibly delivered or read).
+- (NSArray<NSString *> *)sentRecipientIds;
+
+// All recipients of this message to whom it has been sent and delivered (and possibly read).
 - (NSArray<NSString *> *)deliveredRecipientIds;
 
 // All recipients of this message to whom it has been sent, delivered and read.
diff --git a/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.m b/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.m
index 1597449e3..c78065105 100644
--- a/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.m
+++ b/SignalServiceKit/src/Messages/Interactions/TSOutgoingMessage.m
@@ -405,6 +405,14 @@ NSString *NSStringForOutgoingMessageRecipientState(OWSOutgoingMessageRecipientSt
     return (self.hasLegacyMessageState && self.legacyWasDelivered && self.messageState == TSOutgoingMessageStateSent);
 }
 
+- (BOOL)wasSentToAnyRecipient
+{
+    if ([self sentRecipientIds].count > 0) {
+        return YES;
+    }
+    return (self.hasLegacyMessageState && self.messageState == TSOutgoingMessageStateSent);
+}
+
 + (TSOutgoingMessageState)messageStateForRecipientStates:(NSArray<TSOutgoingMessageRecipientState *> *)recipientStates
 {
     OWSAssertDebug(recipientStates);
@@ -509,6 +517,18 @@ NSString *NSStringForOutgoingMessageRecipientState(OWSOutgoingMessageRecipientSt
     return result;
 }
 
+- (NSArray<NSString *> *)sentRecipientIds
+{
+    NSMutableArray<NSString *> *result = [NSMutableArray new];
+    for (NSString *recipientId in self.recipientStateMap) {
+        TSOutgoingMessageRecipientState *recipientState = self.recipientStateMap[recipientId];
+        if (recipientState.state == OWSOutgoingMessageRecipientStateSent) {
+            [result addObject:recipientId];
+        }
+    }
+    return result;
+}
+
 - (NSArray<NSString *> *)deliveredRecipientIds
 {
     NSMutableArray<NSString *> *result = [NSMutableArray new];
diff --git a/SignalServiceKit/src/Messages/OWSMessageSender.m b/SignalServiceKit/src/Messages/OWSMessageSender.m
index cc55cedff..ab1969ca0 100644
--- a/SignalServiceKit/src/Messages/OWSMessageSender.m
+++ b/SignalServiceKit/src/Messages/OWSMessageSender.m
@@ -619,11 +619,26 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
 
 - (void)sendMessageToService:(TSOutgoingMessage *)message
            senderCertificate:(nullable SMKSenderCertificate *)senderCertificate
-                     success:(void (^)(void))successHandler
-                     failure:(RetryableFailureHandler)failureHandler
+                     success:(void (^)(void))successHandlerParam
+                     failure:(RetryableFailureHandler)failureHandlerParam
 {
     AssertIsOnSendingQueue();
 
+    void (^successHandler)(void) = ^() {
+        dispatch_async([OWSDispatch sendingQueue], ^{
+            [self handleMessageSentLocally:message senderCertificate:senderCertificate];
+        });
+        successHandlerParam();
+    };
+    void (^failureHandler)(NSError *) = ^(NSError *error) {
+        if (message.wasSentToAnyRecipient) {
+            dispatch_async([OWSDispatch sendingQueue], ^{
+                [self handleMessageSentLocally:message senderCertificate:senderCertificate];
+            });
+        }
+        failureHandlerParam(error);
+    };
+
     TSThread *_Nullable thread = message.thread;
 
     // In the "self-send" special case, we ony need to send a sync message with a delivery receipt.
@@ -638,9 +653,6 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
                                        transaction:transaction];
             }
         }];
-
-        [self handleMessageSentLocally:message senderCertificate:senderCertificate];
-
         successHandler();
         return;
     }
@@ -1103,8 +1115,6 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
             [SignalRecipient markRecipientAsRegisteredAndGet:recipient.recipientId transaction:transaction];
         }];
 
-        [self handleMessageSentLocally:messageSend.message
-                     senderCertificate:messageSend.unidentifiedAccess.senderCertificate];
         messageSend.success();
     });
 }
@@ -1273,6 +1283,10 @@ NSString *const OWSMessageSenderRateLimitedException = @"RateLimitedException";
     if (message.shouldSyncTranscript) {
         // TODO: I suspect we shouldn't optimistically set hasSyncedTranscript.
         //       We could set this in a success handler for [sendSyncTranscriptForMessage:].
+        // TODO: We might send to a recipient, then to another recipient on retry.
+        //       To ensure desktop receives all "delivery status" info, we might
+        //       want to send a transcript after every send that reaches _any_
+        //       new recipients.
         [self.dbConnection readWriteWithBlock:^(YapDatabaseReadWriteTransaction *transaction) {
             [message updateWithHasSyncedTranscript:YES transaction:transaction];
         }];