diff --git a/Session/Conversations/ConversationVC.swift b/Session/Conversations/ConversationVC.swift
index a48223371..35f5e1dde 100644
--- a/Session/Conversations/ConversationVC.swift
+++ b/Session/Conversations/ConversationVC.swift
@@ -353,6 +353,7 @@ final class ConversationVC : BaseVC, ConversationViewModelDelegate, OWSConversat
                 case .delete:
                     self.messagesTableView.deleteRows(at: [ IndexPath(row: Int(update.oldIndex), section: 0) ], with: .fade)
                 case .insert:
+                    print("[Test] INSERT")
                     // Perform inserts before updates
                     self.messagesTableView.insertRows(at: [ IndexPath(row: Int(update.newIndex), section: 0) ], with: .fade)
                     if update.viewItem?.interaction is TSOutgoingMessage {
diff --git a/SessionMessagingKit/Sending & Receiving/MessageSender.swift b/SessionMessagingKit/Sending & Receiving/MessageSender.swift
index 8b4cfdff0..4994a13a1 100644
--- a/SessionMessagingKit/Sending & Receiving/MessageSender.swift	
+++ b/SessionMessagingKit/Sending & Receiving/MessageSender.swift	
@@ -337,10 +337,12 @@ public final class MessageSender : NSObject {
                 let thread = TSGroupThread.fetch(uniqueId: threadID, transaction: transaction), thread.isClosedGroup {
                 recipients = thread.groupModel.groupMemberIds
             }
-            recipients.forEach { recipient in
-                tsMessage.update(withSentRecipient: recipient, wasSentByUD: true, transaction: transaction)
+            if !tsMessage.wasSentToAnyRecipient {
+                recipients.forEach { recipient in
+                    tsMessage.update(withSentRecipient: recipient, wasSentByUD: true, transaction: transaction)
+                }
+                MessageInvalidator.invalidate(tsMessage, with: transaction)
             }
-            MessageInvalidator.invalidate(tsMessage, with: transaction)
             // Start the disappearing messages timer if needed
             OWSDisappearingMessagesJob.shared().startAnyExpiration(for: tsMessage, expirationStartedAt: NSDate.millisecondTimestamp(), transaction: transaction)
         }
@@ -359,6 +361,8 @@ public final class MessageSender : NSObject {
 
     public static func handleFailedMessageSend(_ message: Message, with error: Swift.Error, using transaction: Any) {
         guard let tsMessage = TSOutgoingMessage.find(withTimestamp: message.sentTimestamp!) else { return }
-        tsMessage.update(sendingError: error, transaction: transaction as! YapDatabaseReadWriteTransaction)
+        let transaction = transaction as! YapDatabaseReadWriteTransaction
+        tsMessage.update(sendingError: error, transaction: transaction)
+        MessageInvalidator.invalidate(tsMessage, with: transaction)
     }
 }
diff --git a/SessionMessagingKit/Utilities/MessageInvalidator.swift b/SessionMessagingKit/Utilities/MessageInvalidator.swift
index 83619e091..2d87e5c38 100644
--- a/SessionMessagingKit/Utilities/MessageInvalidator.swift
+++ b/SessionMessagingKit/Utilities/MessageInvalidator.swift
@@ -11,7 +11,7 @@
     private override init() { }
     
     @objc public static func invalidate(_ message: TSMessage, with transaction: YapDatabaseReadWriteTransaction) {
-        guard let id = message.uniqueId else { return }
+        guard let id = message.uniqueId, !isInvalidated(message) else { return }
         invalidatedMessages.insert(id)
         message.touch(with: transaction)
     }