diff --git a/Signal/src/Models/MessageActions.swift b/Signal/src/Models/MessageActions.swift
index 07c65f42a..70dedc60b 100644
--- a/Signal/src/Models/MessageActions.swift
+++ b/Signal/src/Models/MessageActions.swift
@@ -71,11 +71,13 @@ struct MessageActionBuilder {
 class ConversationViewItemActions: NSObject {
 
     @objc
-    class func textActions(conversationViewItem: ConversationViewItem, delegate: MessageActionsDelegate) -> [MenuAction] {
+    class func textActions(conversationViewItem: ConversationViewItem, shouldAllowReply: Bool, delegate: MessageActionsDelegate) -> [MenuAction] {
         var actions: [MenuAction] = []
 
-        let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
-        actions.append(replyAction)
+        if shouldAllowReply {
+            let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
+            actions.append(replyAction)
+        }
 
         if conversationViewItem.hasBodyTextActionContent {
             let copyTextAction = MessageActionBuilder.copyText(conversationViewItem: conversationViewItem, delegate: delegate)
@@ -92,11 +94,13 @@ class ConversationViewItemActions: NSObject {
     }
 
     @objc
-    class func mediaActions(conversationViewItem: ConversationViewItem, delegate: MessageActionsDelegate) -> [MenuAction] {
+    class func mediaActions(conversationViewItem: ConversationViewItem, shouldAllowReply: Bool, delegate: MessageActionsDelegate) -> [MenuAction] {
         var actions: [MenuAction] = []
 
-        let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
-        actions.append(replyAction)
+        if shouldAllowReply {
+            let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
+            actions.append(replyAction)
+        }
 
         if conversationViewItem.hasMediaActionContent {
             if conversationViewItem.canCopyMedia() {
@@ -119,18 +123,26 @@ class ConversationViewItemActions: NSObject {
     }
 
     @objc
-    class func quotedMessageActions(conversationViewItem: ConversationViewItem, delegate: MessageActionsDelegate) -> [MenuAction] {
-        let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
+    class func quotedMessageActions(conversationViewItem: ConversationViewItem, shouldAllowReply: Bool, delegate: MessageActionsDelegate) -> [MenuAction] {
+        var actions: [MenuAction] = []
+
+        if shouldAllowReply {
+            let replyAction = MessageActionBuilder.reply(conversationViewItem: conversationViewItem, delegate: delegate)
+            actions.append(replyAction)
+        }
+
         let deleteAction = MessageActionBuilder.deleteMessage(conversationViewItem: conversationViewItem, delegate: delegate)
+        actions.append(deleteAction)
+
         let showDetailsAction = MessageActionBuilder.showDetails(conversationViewItem: conversationViewItem, delegate: delegate)
+        actions.append(showDetailsAction)
 
-        return [replyAction, deleteAction, showDetailsAction]
+        return actions
     }
 
     @objc
     class func infoMessageActions(conversationViewItem: ConversationViewItem, delegate: MessageActionsDelegate) -> [MenuAction] {
         let deleteAction = MessageActionBuilder.deleteMessage(conversationViewItem: conversationViewItem, delegate: delegate)
-
-        return [deleteAction]
+        return [deleteAction ]
     }
 }
diff --git a/Signal/src/ViewControllers/ConversationView/Cells/ConversationViewCell.h b/Signal/src/ViewControllers/ConversationView/Cells/ConversationViewCell.h
index 1b4f94496..d8617b62f 100644
--- a/Signal/src/ViewControllers/ConversationView/Cells/ConversationViewCell.h
+++ b/Signal/src/ViewControllers/ConversationView/Cells/ConversationViewCell.h
@@ -21,9 +21,15 @@ NS_ASSUME_NONNULL_BEGIN
 
 @protocol ConversationViewCellDelegate <NSObject>
 
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressTextViewItem:(id<ConversationViewItem>)viewItem;
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressMediaViewItem:(id<ConversationViewItem>)viewItem;
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressQuoteViewItem:(id<ConversationViewItem>)viewItem;
+- (void)conversationCell:(ConversationViewCell *)cell
+            shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressTextViewItem:(id<ConversationViewItem>)viewItem;
+- (void)conversationCell:(ConversationViewCell *)cell
+             shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressMediaViewItem:(id<ConversationViewItem>)viewItem;
+- (void)conversationCell:(ConversationViewCell *)cell
+             shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressQuoteViewItem:(id<ConversationViewItem>)viewItem;
 - (void)conversationCell:(ConversationViewCell *)cell
     didLongpressSystemMessageViewItem:(id<ConversationViewItem>)viewItem;
 
diff --git a/Signal/src/ViewControllers/ConversationView/Cells/OWSMessageCell.m b/Signal/src/ViewControllers/ConversationView/Cells/OWSMessageCell.m
index 185349db6..a8429c7aa 100644
--- a/Signal/src/ViewControllers/ConversationView/Cells/OWSMessageCell.m
+++ b/Signal/src/ViewControllers/ConversationView/Cells/OWSMessageCell.m
@@ -423,14 +423,15 @@ NS_ASSUME_NONNULL_BEGIN
         return;
     }
 
+    BOOL shouldAllowReply = YES;
     if (self.viewItem.interaction.interactionType == OWSInteractionType_OutgoingMessage) {
         TSOutgoingMessage *outgoingMessage = (TSOutgoingMessage *)self.viewItem.interaction;
         if (outgoingMessage.messageState == TSOutgoingMessageStateFailed) {
-            // Ignore long press on unsent messages.
-            return;
+            // Don't allow "delete" or "reply" on "failed" outgoing messages.
+            shouldAllowReply = NO;
         } else if (outgoingMessage.messageState == TSOutgoingMessageStateSending) {
-            // Ignore long press on outgoing messages being sent.
-            return;
+            // Don't allow "delete" or "reply" on "sending" outgoing messages.
+            shouldAllowReply = NO;
         }
     }
 
@@ -438,15 +439,21 @@ NS_ASSUME_NONNULL_BEGIN
     switch ([self.messageBubbleView gestureLocationForLocation:locationInMessageBubble]) {
         case OWSMessageGestureLocation_Default:
         case OWSMessageGestureLocation_OversizeText: {
-            [self.delegate conversationCell:self didLongpressTextViewItem:self.viewItem];
+            [self.delegate conversationCell:self
+                           shouldAllowReply:shouldAllowReply
+                   didLongpressTextViewItem:self.viewItem];
             break;
         }
         case OWSMessageGestureLocation_Media: {
-            [self.delegate conversationCell:self didLongpressMediaViewItem:self.viewItem];
+            [self.delegate conversationCell:self
+                           shouldAllowReply:shouldAllowReply
+                  didLongpressMediaViewItem:self.viewItem];
             break;
         }
         case OWSMessageGestureLocation_QuotedReply: {
-            [self.delegate conversationCell:self didLongpressQuoteViewItem:self.viewItem];
+            [self.delegate conversationCell:self
+                           shouldAllowReply:shouldAllowReply
+                  didLongpressQuoteViewItem:self.viewItem];
             break;
         }
     }
diff --git a/Signal/src/ViewControllers/ConversationView/ConversationViewController.m b/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
index 1b6346221..3284f28a3 100644
--- a/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
+++ b/Signal/src/ViewControllers/ConversationView/ConversationViewController.m
@@ -1923,24 +1923,36 @@ typedef enum : NSUInteger {
 
 #pragma mark - ConversationViewCellDelegate
 
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressMediaViewItem:(id<ConversationViewItem>)viewItem
+- (void)conversationCell:(ConversationViewCell *)cell
+             shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressMediaViewItem:(id<ConversationViewItem>)viewItem
 {
     NSArray<MenuAction *> *messageActions =
-        [ConversationViewItemActions mediaActionsWithConversationViewItem:viewItem delegate:self];
+        [ConversationViewItemActions mediaActionsWithConversationViewItem:viewItem
+                                                         shouldAllowReply:shouldAllowReply
+                                                                 delegate:self];
     [self presentMessageActions:messageActions withFocusedCell:cell];
 }
 
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressTextViewItem:(id<ConversationViewItem>)viewItem
+- (void)conversationCell:(ConversationViewCell *)cell
+            shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressTextViewItem:(id<ConversationViewItem>)viewItem
 {
     NSArray<MenuAction *> *messageActions =
-        [ConversationViewItemActions textActionsWithConversationViewItem:viewItem delegate:self];
+        [ConversationViewItemActions textActionsWithConversationViewItem:viewItem
+                                                        shouldAllowReply:shouldAllowReply
+                                                                delegate:self];
     [self presentMessageActions:messageActions withFocusedCell:cell];
 }
 
-- (void)conversationCell:(ConversationViewCell *)cell didLongpressQuoteViewItem:(id<ConversationViewItem>)viewItem
+- (void)conversationCell:(ConversationViewCell *)cell
+             shouldAllowReply:(BOOL)shouldAllowReply
+    didLongpressQuoteViewItem:(id<ConversationViewItem>)viewItem
 {
     NSArray<MenuAction *> *messageActions =
-        [ConversationViewItemActions quotedMessageActionsWithConversationViewItem:viewItem delegate:self];
+        [ConversationViewItemActions quotedMessageActionsWithConversationViewItem:viewItem
+                                                                 shouldAllowReply:shouldAllowReply
+                                                                         delegate:self];
     [self presentMessageActions:messageActions withFocusedCell:cell];
 }