diff --git a/api/server/routes/ask.js b/api/server/routes/ask.js
index ea246fb46d..794f6367b1 100644
--- a/api/server/routes/ask.js
+++ b/api/server/routes/ask.js
@@ -19,7 +19,7 @@ router.use('/sydney', askSydney);
 router.post('/', async (req, res) => {
   let { model, text, parentMessageId, conversationId: oldConversationId , chatGptLabel, promptPrefix } = req.body;
   if (text.length === 0) {
-    return handleError(res, 'Prompt empty or too short');
+    return handleError(res, { text: 'Prompt empty or too short' });
   }
 
   const conversationId = oldConversationId || crypto.randomUUID();
@@ -135,7 +135,7 @@ router.post('/', async (req, res) => {
         messageId: crypto.randomUUID(), sender: model, 
         conversationId, parentMessageId: userMessageId,
         error: true, text: 'Prompt empty or too short'});
-      return handleError(res, 'Prompt empty or too short');
+      return handleError(res, { text: 'Prompt empty or too short' });
     }
 
     gptResponse.sender = model === 'chatgptCustom' ? chatGptLabel : model;
@@ -175,11 +175,12 @@ router.post('/', async (req, res) => {
   } catch (error) {
     console.log(error);
     // await deleteMessages({ messageId: userMessageId });
-    await saveMessage({ 
+    const errorMessage = { 
       messageId: crypto.randomUUID(), sender: model, 
-      conversationId, parentMessageId: userMessageId,
-      error: true, text: error.message});
-    handleError(res, error.message);
+      conversationId, parentMessageId: overrideParentMessageId || userMessageId,
+      error: true, text: error.message}
+    await saveMessage(errorMessage);
+    handleError(res, errorMessage);
   }
 });
 
diff --git a/api/server/routes/askBing.js b/api/server/routes/askBing.js
index 975046986c..885741d08c 100644
--- a/api/server/routes/askBing.js
+++ b/api/server/routes/askBing.js
@@ -9,7 +9,7 @@ const citationRegex = /\[\^\d+?\^]/g;
 router.post('/', async (req, res) => {
   const { model, text, parentMessageId, conversationId: oldConversationId, ...convo } = req.body;
   if (text.length === 0) {
-    return handleError(res, 'Prompt empty or too short');
+    return handleError(res, { text: 'Prompt empty or too short' });
   }
 
   const conversationId = oldConversationId || crypto.randomUUID();
@@ -112,11 +112,12 @@ router.post('/', async (req, res) => {
   } catch (error) {
     console.log(error);
     // await deleteMessages({ messageId: userMessageId });
-    await saveMessage({ 
+    const errorMessage = { 
       messageId: crypto.randomUUID(), sender: model, 
-      conversationId, parentMessageId: userMessageId,
-      error: true, text: error.message});
-    handleError(res, error.message);
+      conversationId, parentMessageId: overrideParentMessageId || userMessageId,
+      error: true, text: error.message}
+    await saveMessage(errorMessage);
+    handleError(res, errorMessage);
   }
 });
 
diff --git a/api/server/routes/askSydney.js b/api/server/routes/askSydney.js
index a31c42e3f0..5a63f97004 100644
--- a/api/server/routes/askSydney.js
+++ b/api/server/routes/askSydney.js
@@ -9,7 +9,7 @@ const citationRegex = /\[\^\d+?\^]/g;
 router.post('/', async (req, res) => {
   const { model, text, parentMessageId, conversationId: oldConversationId, ...convo } = req.body;
   if (text.length === 0) {
-    return handleError(res, 'Prompt empty or too short');
+    return handleError(res, { text: 'Prompt empty or too short' });
   }
 
   const conversationId = oldConversationId || crypto.randomUUID();
@@ -123,11 +123,12 @@ router.post('/', async (req, res) => {
   } catch (error) {
     console.log(error);
     // await deleteMessages({ messageId: userMessageId });
-    await saveMessage({ 
+    const errorMessage = { 
       messageId: crypto.randomUUID(), sender: model, 
-      conversationId, parentMessageId: userMessageId,
-      error: true, text: error.message});
-    handleError(res, error.message);
+      conversationId, parentMessageId: overrideParentMessageId || userMessageId,
+      error: true, text: error.message}
+    await saveMessage(errorMessage);
+    handleError(res, errorMessage);
   }
 });
 
diff --git a/api/server/routes/handlers.js b/api/server/routes/handlers.js
index edd64e6184..e727cacfa3 100644
--- a/api/server/routes/handlers.js
+++ b/api/server/routes/handlers.js
@@ -1,5 +1,5 @@
-const handleError = (res, errorMessage) => {
-  res.status(500).write(`event: error\ndata: ${errorMessage}`);
+const handleError = (res, message) => {
+  res.write(`event: error\ndata: ${JSON.stringify(message)}\n\n`);
   res.end();
 };
 
diff --git a/client/src/components/Main/TextChat.jsx b/client/src/components/Main/TextChat.jsx
index 710b10f7c2..0045718617 100644
--- a/client/src/components/Main/TextChat.jsx
+++ b/client/src/components/Main/TextChat.jsx
@@ -128,18 +128,17 @@ export default function TextChat({ messages }) {
     dispatch(setSubmitState(false));
   };
 
-  const errorHandler = (event, currentState, currentMsg) => {
+  const errorHandler = (data, currentState, currentMsg) => {
     const { initialResponse, messages, _currentMsg, message } = currentState;
-    console.log('Error:', event);
+    console.log('Error:', data);
     const errorResponse = {
-      ...initialResponse,
-      text: `${event.data}`,
+      ...data,
       error: true,
       parentMessageId: currentMsg?.messageId,
     };
-    setErrorMessage(event.data);
+    setErrorMessage(data?.text);
     dispatch(setSubmitState(false));
-    dispatch(setMessages([...messages.slice(0, -2), currentMsg, errorResponse]));
+    dispatch(setMessages([...messages, currentMsg, errorResponse]));
     dispatch(setText(message?.text));
     dispatch(setError(true));
     return;
@@ -265,7 +264,10 @@ export default function TextChat({ messages }) {
     events.onerror = function (e) {
       console.log('error in opening conn.');
       events.close();
-      errorHandler(e, currentState, currentMsg);
+
+      const data = JSON.parse(e.data);
+
+      errorHandler(data, currentState, currentMsg);
     };
 
     events.stream();