diff --git a/src/Simplex/Chat.hs b/src/Simplex/Chat.hs
index 99413bc3ee..a5762eea76 100644
--- a/src/Simplex/Chat.hs
+++ b/src/Simplex/Chat.hs
@@ -118,11 +118,6 @@ import qualified UnliftIO.Exception as E
 import UnliftIO.IO (hClose, hSeek, hTell, openFile)
 import UnliftIO.STM
 
--- this limit reserves space for metadata in forwarded messages
--- 15780 (limit used for fileChunkSize) - 161 (x.grp.msg.forward overhead) = 15619, round to 15610
-maxChatMsgSize :: Int
-maxChatMsgSize = 15610
-
 defaultChatConfig :: ChatConfig
 defaultChatConfig =
   ChatConfig
@@ -3714,6 +3709,7 @@ processAgentMessageConn user@User {userId} corrId agentConnId agentMessage = do
         checkIntegrityCreateItem (CDGroupRcv gInfo m) msgMeta `catchChatError` \_ -> pure ()
         cmdId <- createAckCmd conn
         let aChatMsgs = parseChatMessages msgBody
+        when (length aChatMsgs > 1) $ liftIO $ putStrLn (show msgBody)
         withAckMessage agentConnId cmdId msgMeta $ do
           forM_ aChatMsgs $ \case
             Right (ACMsg _ chatMsg) ->
@@ -5611,9 +5607,11 @@ createSndMessage :: (MsgEncodingI e, ChatMonad m) => ChatMsgEvent e -> ConnOrGro
 createSndMessage chatMsgEvent connOrGroupId = do
   gVar <- asks idsDrg
   ChatConfig {chatVRange} <- asks config
-  withStore $ \db -> createNewSndMessage db gVar connOrGroupId $ \sharedMsgId ->
-    let msgBody = encodeChatMessage ChatMessage {chatVRange, msgId = Just sharedMsgId, chatMsgEvent}
-     in NewMessage {chatMsgEvent, msgBody}
+  withStore $ \db -> createNewSndMessage db gVar connOrGroupId (newMsg chatVRange)
+  where
+    newMsg chatVRange sharedMsgId = do
+      let r = encodeChatMessage ChatMessage {chatVRange, msgId = Just sharedMsgId, chatMsgEvent}
+      fmap (NewMessage chatMsgEvent) r
 
 sendBatchedDirectMessages :: forall e m. (MsgEncodingI e, ChatMonad m) => Connection -> NonEmpty (ChatMsgEvent e) -> ConnOrGroupId -> m ()
 sendBatchedDirectMessages conn@Connection {connId} events connOrGroupId = do
@@ -5636,9 +5634,9 @@ sendBatchedDirectMessages conn@Connection {connId} events connOrGroupId = do
       ChatConfig {chatVRange} <- asks config
       withStore' $ \db -> forM (toList events) $ \event ->
         runExceptT $ createNewSndMessage db gVar connOrGroupId (newMsg chatVRange event)
-    newMsg chatVRange chatMsgEvent sharedMsgId =
-      let msgBody = encodeChatMessage ChatMessage {chatVRange, msgId = Just sharedMsgId, chatMsgEvent}
-       in NewMessage {chatMsgEvent, msgBody}
+    newMsg chatVRange chatMsgEvent sharedMsgId = do
+      let r = encodeChatMessage ChatMessage {chatVRange, msgId = Just sharedMsgId, chatMsgEvent}
+      fmap (NewMessage chatMsgEvent) r
     partitionBatches :: [ChatMessageBatch] -> ([SndMessage], [MessagesBatch])
     partitionBatches = foldr partition' ([], [])
       where
@@ -5679,7 +5677,10 @@ batchChatMessages = mkBatch []
 directMessage :: (MsgEncodingI e, ChatMonad m) => ChatMsgEvent e -> m ByteString
 directMessage chatMsgEvent = do
   ChatConfig {chatVRange} <- asks config
-  pure $ encodeChatMessage ChatMessage {chatVRange, msgId = Nothing, chatMsgEvent}
+  let r = encodeChatMessage ChatMessage {chatVRange, msgId = Nothing, chatMsgEvent}
+  case r of
+    Left e -> throwChatError $ CEException e
+    Right encodedBody -> pure encodedBody
 
 deliverMessage :: ChatMonad m => Connection -> CMEventTag e -> MsgBody -> MessageId -> m Int64
 deliverMessage conn cmEventTag msgBody msgId = do
diff --git a/src/Simplex/Chat/Protocol.hs b/src/Simplex/Chat/Protocol.hs
index af4f643416..449901b2b8 100644
--- a/src/Simplex/Chat/Protocol.hs
+++ b/src/Simplex/Chat/Protocol.hs
@@ -483,10 +483,19 @@ data ExtMsgContent = ExtMsgContent {content :: MsgContent, file :: Maybe FileInv
 
 $(JQ.deriveJSON defaultJSON ''QuotedMsg)
 
-encodeChatMessage :: MsgEncodingI e => ChatMessage e -> ByteString
-encodeChatMessage msg = case chatToAppMessage msg of
-  AMJson m -> LB.toStrict $ J.encode m
-  AMBinary m -> strEncode m
+-- this limit reserves space for metadata in forwarded messages
+-- 15780 (limit used for fileChunkSize) - 161 (x.grp.msg.forward overhead) = 15619, round to 15610
+maxChatMsgSize :: Int
+maxChatMsgSize = 15610
+
+encodeChatMessage :: MsgEncodingI e => ChatMessage e -> Either String ByteString
+encodeChatMessage msg = do
+  let body = case chatToAppMessage msg of
+        AMJson m -> LB.toStrict $ J.encode m
+        AMBinary m -> strEncode m
+  if B.length body > maxChatMsgSize
+    then Left "large message"
+    else Right body
 
 parseChatMessages :: ByteString -> [Either String AChatMessage]
 parseChatMessages "" = [Left "empty string"]
diff --git a/src/Simplex/Chat/Store/Messages.hs b/src/Simplex/Chat/Store/Messages.hs
index 82acd646c7..2bae6cd28e 100644
--- a/src/Simplex/Chat/Store/Messages.hs
+++ b/src/Simplex/Chat/Store/Messages.hs
@@ -160,22 +160,24 @@ deleteGroupCIs db User {userId} GroupInfo {groupId} = do
   DB.execute db "DELETE FROM chat_item_reactions WHERE group_id = ?" (Only groupId)
   DB.execute db "DELETE FROM chat_items WHERE user_id = ? AND group_id = ?" (userId, groupId)
 
-createNewSndMessage :: MsgEncodingI e => DB.Connection -> TVar ChaChaDRG -> ConnOrGroupId -> (SharedMsgId -> NewMessage e) -> ExceptT StoreError IO SndMessage
+createNewSndMessage :: MsgEncodingI e => DB.Connection -> TVar ChaChaDRG -> ConnOrGroupId -> (SharedMsgId -> Either String (NewMessage e)) -> ExceptT StoreError IO SndMessage
 createNewSndMessage db gVar connOrGroupId mkMessage =
-  createWithRandomId gVar $ \sharedMsgId -> do
-    let NewMessage {chatMsgEvent, msgBody} = mkMessage $ SharedMsgId sharedMsgId
-    createdAt <- getCurrentTime
-    DB.execute
-      db
-      [sql|
-        INSERT INTO messages (
-          msg_sent, chat_msg_event, msg_body, connection_id, group_id,
-          shared_msg_id, shared_msg_id_user, created_at, updated_at
-        ) VALUES (?,?,?,?,?,?,?,?,?)
-      |]
-      (MDSnd, toCMEventTag chatMsgEvent, msgBody, connId_, groupId_, sharedMsgId, Just True, createdAt, createdAt)
-    msgId <- insertedRowId db
-    pure SndMessage {msgId, sharedMsgId = SharedMsgId sharedMsgId, msgBody}
+  createWithRandomId' gVar $ \sharedMsgId ->
+    case mkMessage (SharedMsgId sharedMsgId) of
+      Left err -> pure $ Left (SEErrorSavingMessage err)
+      Right NewMessage {chatMsgEvent, msgBody} -> do
+        createdAt <- getCurrentTime
+        DB.execute
+          db
+          [sql|
+            INSERT INTO messages (
+              msg_sent, chat_msg_event, msg_body, connection_id, group_id,
+              shared_msg_id, shared_msg_id_user, created_at, updated_at
+            ) VALUES (?,?,?,?,?,?,?,?,?)
+          |]
+          (MDSnd, toCMEventTag chatMsgEvent, msgBody, connId_, groupId_, sharedMsgId, Just True, createdAt, createdAt)
+        msgId <- insertedRowId db
+        pure $ Right SndMessage {msgId, sharedMsgId = SharedMsgId sharedMsgId, msgBody}
   where
     (connId_, groupId_) = case connOrGroupId of
       ConnectionId connId -> (Just connId, Nothing)
diff --git a/src/Simplex/Chat/Store/Shared.hs b/src/Simplex/Chat/Store/Shared.hs
index 6fb77b5484..b86c14ca5e 100644
--- a/src/Simplex/Chat/Store/Shared.hs
+++ b/src/Simplex/Chat/Store/Shared.hs
@@ -85,6 +85,7 @@ data StoreError
   | SEPendingConnectionNotFound {connId :: Int64}
   | SEIntroNotFound
   | SEUniqueID
+  | SEErrorSavingMessage {message :: String}
   | SEInternalError {message :: String}
   | SEBadChatItem {itemId :: ChatItemId}
   | SEChatItemNotFound {itemId :: ChatItemId}
@@ -374,15 +375,22 @@ withLocalDisplayName db userId displayName action = getLdnSuffix >>= (`tryCreate
 createWithRandomId :: forall a. TVar ChaChaDRG -> (ByteString -> IO a) -> ExceptT StoreError IO a
 createWithRandomId = createWithRandomBytes 12
 
+createWithRandomId' :: forall a. TVar ChaChaDRG -> (ByteString -> IO (Either StoreError a)) -> ExceptT StoreError IO a
+createWithRandomId' = createWithRandomBytes' 12
+
 createWithRandomBytes :: forall a. Int -> TVar ChaChaDRG -> (ByteString -> IO a) -> ExceptT StoreError IO a
-createWithRandomBytes size gVar create = tryCreate 3
+createWithRandomBytes size gVar create = createWithRandomBytes' size gVar (fmap Right . create)
+
+createWithRandomBytes' :: forall a. Int -> TVar ChaChaDRG -> (ByteString -> IO (Either StoreError a)) -> ExceptT StoreError IO a
+createWithRandomBytes' size gVar create = tryCreate 3
   where
     tryCreate :: Int -> ExceptT StoreError IO a
     tryCreate 0 = throwError SEUniqueID
     tryCreate n = do
       id' <- liftIO $ encodedRandomBytes gVar size
       liftIO (E.try $ create id') >>= \case
-        Right x -> pure x
+        Right (Right x) -> pure x
+        Right (Left e) -> throwError e
         Left e
           | SQL.sqlError e == SQL.ErrorConstraint -> tryCreate (n - 1)
           | otherwise -> throwError . SEInternalError $ show e
diff --git a/tests/ProtocolTests.hs b/tests/ProtocolTests.hs
index db8028f667..5c6b51d3dc 100644
--- a/tests/ProtocolTests.hs
+++ b/tests/ProtocolTests.hs
@@ -69,9 +69,13 @@ s ==## msg = do
     _ -> expectationFailure "exactly one message expected"
 
 (##==) :: MsgEncodingI e => ByteString -> ChatMessage e -> Expectation
-s ##== msg =
-  J.eitherDecodeStrict' (encodeChatMessage msg)
-    `shouldBe` (J.eitherDecodeStrict' s :: Either String J.Value)
+s ##== msg = do
+  let r = encodeChatMessage msg
+  case r of
+    Left e -> expectationFailure $ "encode error: " <> show e
+    Right encodedBody ->
+      J.eitherDecodeStrict' encodedBody
+        `shouldBe` (J.eitherDecodeStrict' s :: Either String J.Value)
 
 (##==##) :: MsgEncodingI e => ByteString -> ChatMessage e -> Expectation
 s ##==## msg = do