diff --git a/src/Simplex/Chat.hs b/src/Simplex/Chat.hs
index d5f06a326f..7ca2f4b948 100644
--- a/src/Simplex/Chat.hs
+++ b/src/Simplex/Chat.hs
@@ -2945,8 +2945,8 @@ processChatCommand' vr = \case
           msgs_ <- sendDirectContactMessages user ct $ L.map XMsgNew msgContainers
           let itemsData = prepareSndItemsData msgs_ cmrs ciFiles_ quotedItems_
           when (length itemsData /= length cmrs) $ logError "sendContactContentMessages: cmrs and itemsData length mismatch"
-          (errs, cis) <- partitionEithers <$> saveSndChatItems user (CDDirectSnd ct) itemsData timed_ live
-          unless (null errs) $ toView $ CRChatErrors (Just user) errs
+          r@(_, cis) <- partitionEithers <$> saveSndChatItems user (CDDirectSnd ct) itemsData timed_ live
+          processSendErrs user r
           forM_ (timed_ >>= timedDeleteAt') $ \deleteAt ->
             forM_ cis $ \ci ->
               startProximateTimedItemThread user (ChatRef CTDirect contactId, chatItemId' ci) deleteAt
@@ -3010,8 +3010,8 @@ processChatCommand' vr = \case
           cis_ <- saveSndChatItems user (CDGroupSnd gInfo) itemsData timed_ live
           when (length itemsData /= length cmrs) $ logError "sendGroupContentMessages: cmrs and cis_ length mismatch"
           createMemberSndStatuses cis_ msgs_ gsr
-          let (errs, cis) = partitionEithers cis_
-          unless (null errs) $ toView $ CRChatErrors (Just user) errs
+          let r@(_, cis) = partitionEithers cis_
+          processSendErrs user r
           forM_ (timed_ >>= timedDeleteAt') $ \deleteAt ->
             forM_ cis $ \ci ->
               startProximateTimedItemThread user (ChatRef CTGroup groupId, chatItemId' ci) deleteAt
@@ -3103,6 +3103,18 @@ processChatCommand' vr = \case
         | (msg_, (ComposedMessage {msgContent}, itemForwarded), f, q) <-
             zipWith4 (,,,) msgs_ (L.toList cmrs') (L.toList ciFiles_) (L.toList quotedItems_)
       ]
+    processSendErrs :: User -> ([ChatError], [ChatItem c d]) -> CM ()
+    processSendErrs user = \case
+      -- no errors
+      ([], _) -> pure ()
+      -- at least one item is successfully created
+      (errs, _ci : _) -> toView $ CRChatErrors (Just user) errs
+      -- single error
+      ([err], []) -> throwError err
+      -- multiple errors
+      (errs@(err : _), []) -> do
+        toView $ CRChatErrors (Just user) errs
+        throwError err
     getCommandDirectChatItems :: User -> Int64 -> NonEmpty ChatItemId -> CM (Contact, [CChatItem 'CTDirect])
     getCommandDirectChatItems user ctId itemIds = do
       ct <- withFastStore $ \db -> getContact db vr user ctId
diff --git a/tests/ChatTests/Direct.hs b/tests/ChatTests/Direct.hs
index 97a9d89200..c47cf975a1 100644
--- a/tests/ChatTests/Direct.hs
+++ b/tests/ChatTests/Direct.hs
@@ -2547,7 +2547,7 @@ setupDesynchronizedRatchet tmp alice = do
     (bob </)
     bob ##> "/tail @alice 1"
     bob <# "alice> decryption error, possibly due to the device change (header, 3 messages)"
-    bob `send` "@alice 1"
+    bob ##> "@alice 1"
     bob <## "error: command is prohibited, sendMessagesB: send prohibited"
     (alice </)
   where