diff --git a/ts/components/conversation/message/MessageContextMenu.tsx b/ts/components/conversation/message/MessageContextMenu.tsx
index 9e97f1b35..59144e1ba 100644
--- a/ts/components/conversation/message/MessageContextMenu.tsx
+++ b/ts/components/conversation/message/MessageContextMenu.tsx
@@ -64,6 +64,7 @@ export const MessageContextMenu = (props: Props) => {
   } = selected;
   const { messageId, contextMenuId } = props;
   const showRetry = status === 'error' && direction === 'outgoing';
+  const isSent = status === 'sent';
   const multipleAttachments = attachments && attachments.length > 1;
 
   const onContextMenuShown = useCallback(() => {
@@ -168,7 +169,7 @@ export const MessageContextMenu = (props: Props) => {
       ) : null}
 
       <Item onClick={copyText}>{window.i18n('copyMessage')}</Item>
-      <Item onClick={onReply}>{window.i18n('replyToMessage')}</Item>
+      {isSent && <Item onClick={onReply}>{window.i18n('replyToMessage')}</Item>}
       <Item onClick={onShowDetail}>{window.i18n('moreInformation')}</Item>
       {showRetry ? <Item onClick={onRetry}>{window.i18n('resend')}</Item> : null}
       {isDeletable ? (
diff --git a/ts/session/sending/MessageSender.ts b/ts/session/sending/MessageSender.ts
index 85cba5f55..13fcedb0a 100644
--- a/ts/session/sending/MessageSender.ts
+++ b/ts/session/sending/MessageSender.ts
@@ -31,6 +31,13 @@ function overwriteOutgoingTimestampWithNetworkTimestamp(message: RawMessage) {
   const contentDecoded = SignalService.Content.decode(plainTextBuffer);
   const { dataMessage, dataExtractionNotification, typingMessage } = contentDecoded;
   if (dataMessage && dataMessage.timestamp && dataMessage.timestamp > 0) {
+    // this is a sync message, do not overwrite the message timestamp
+    if (dataMessage.syncTarget) {
+      return {
+        overRiddenTimestampBuffer: plainTextBuffer,
+        diffTimestamp: _.toNumber(dataMessage.timestamp),
+      };
+    }
     dataMessage.timestamp = diffTimestamp;
   }
   if (
@@ -86,7 +93,8 @@ export async function send(
       // and the isDuplicate messages relies on sent_at timestamp to be valid.
       const found = await Data.getMessageById(message.identifier);
 
-      if (found) {
+      // make sure to not update the send timestamp if this a currently syncing message
+      if (found && !found.get('sentSync')) {
         found.set({ sent_at: diffTimestamp });
         await found.commit();
       }