diff --git a/api/models/Conversation.js b/api/models/Conversation.js
index 97cb8eaad1..1ff778e957 100644
--- a/api/models/Conversation.js
+++ b/api/models/Conversation.js
@@ -47,6 +47,15 @@ const convoSchema = mongoose.Schema({
 const Conversation =
   mongoose.models.Conversation || mongoose.model('Conversation', convoSchema);
 
+const getConvo = async (conversationId) => {
+  try {
+    return await Conversation.findOne({ conversationId }).exec();
+  } catch (error) {
+    console.log(error);
+    return { message: 'Error getting single conversation' };
+  }
+};
+
 module.exports = {
   saveConvo: async ({ conversationId, title, ...convo }) => {
     try {
@@ -95,12 +104,14 @@ module.exports = {
       return { message: 'Error getting conversations' };
     }
   },
-  getConvo: async (conversationId) => {
+  getConvo,
+  getConvoTitle: async (conversationId) => {
     try {
-      return await Conversation.findOne({ conversationId }).exec();
+      const convo = await getConvo(conversationId);
+      return convo.title;
     } catch (error) {
       console.log(error);
-      return { message: 'Error getting single conversation' };
+      return { message: 'Error getting conversation title' };
     }
   },
   deleteConvos: async (filter) => {
diff --git a/api/models/index.js b/api/models/index.js
index 0b195d7248..8af5a1aa9c 100644
--- a/api/models/index.js
+++ b/api/models/index.js
@@ -1,10 +1,11 @@
 const { saveMessage, deleteMessages } = require('./Message');
 const { getCustomGpts, updateCustomGpt, updateByLabel, deleteCustomGpts } = require('./CustomGpt');
-const { getConvo, saveConvo } = require('./Conversation');
+const { getConvoTitle, getConvo, saveConvo } = require('./Conversation');
 
 module.exports = {
   saveMessage,
   deleteMessages,
+  getConvoTitle,
   getConvo,
   saveConvo,
   getCustomGpts,
diff --git a/api/server/routes/askSydney.js b/api/server/routes/askSydney.js
index 0b77526b8b..a928bc75fc 100644
--- a/api/server/routes/askSydney.js
+++ b/api/server/routes/askSydney.js
@@ -2,7 +2,7 @@ const express = require('express');
 const crypto = require('crypto');
 const router = express.Router();
 const { titleConvo, askSydney } = require('../../app/');
-const { saveMessage, deleteMessages, saveConvo } = require('../../models');
+const { saveMessage, deleteMessages, saveConvo, getConvoTitle } = require('../../models');
 const { handleError, sendMessage } = require('./handlers');
 
 router.post('/', async (req, res) => {
@@ -39,31 +39,48 @@ router.post('/', async (req, res) => {
     });
 
     console.log('SYDNEY RESPONSE');
-    // console.dir(response, { depth: null });
+    // the usual values expected by the client are generated since only
+    // jailbreakConversationId and initial messageId is needed by sydney
+    // to continue the conversation
+    // if (!convo.jailbreakConversationId) {
+    //   response.title = await titleConvo({
+    //     model,
+    //     message: text,
+    //     response: JSON.stringify(response.response)
+    //   });
+    // }
 
-    userMessage.conversationSignature =
-      convo.conversationSignature || response.conversationSignature;
-    userMessage.conversationId = convo.conversationId || response.conversationId;
-    userMessage.invocationId = response.invocationId;
-    userMessage.jailbreakConversationId = convo.jailbreakConversationId || response.jailbreakConversationId;
-    await saveMessage(userMessage);
-    
-    if (!convo.conversationSignature) {
-      response.title = await titleConvo({
-        model,
-        message: text,
-        response: JSON.stringify(response.response)
-      });
-    }
-    
+    // Save sydney response
+    response.id = response.messageId;
+    // response.parentMessageId = convo.parentMessageId ? convo.parentMessageId : response.messageId;
+    response.parentMessageId = response.messageId;
+    response.invocationId = convo.invocationId ? convo.invocationId + 1 : 1;
+    response.title = convo.jailbreakConversationId
+      ? await getConvoTitle(convo.conversationId)
+      : await titleConvo({
+          model,
+          message: text,
+          response: JSON.stringify(response.response)
+        });
+    response.conversationId = convo.conversationId
+      ? convo.conversationId
+      : crypto.randomUUID();
+    response.conversationSignature = convo.conversationSignature
+      ? convo.conversationSignature
+      : crypto.randomUUID();
     response.text = response.response;
-    response.parentMessageId = convo.parentMessageId || response.messageId;
-    response.id = response.details.messageId;
     response.suggestions =
       response.details.suggestedResponses &&
       response.details.suggestedResponses.map((s) => s.text);
     response.sender = model;
     response.final = true;
+
+    // Save user message
+    userMessage.conversationId = response.conversationId;
+    userMessage.parentMessageId = response.parentMessageId;
+    await saveMessage(userMessage);
+
+    // Save sydney response & convo, then send
     await saveMessage(response);
     await saveConvo(response);
     sendMessage(res, response);
diff --git a/client/src/components/Conversations/Conversation.jsx b/client/src/components/Conversations/Conversation.jsx
index 455d331d07..745671e1cc 100644
--- a/client/src/components/Conversations/Conversation.jsx
+++ b/client/src/components/Conversations/Conversation.jsx
@@ -44,7 +44,7 @@ export default function Conversation({
       dispatch(
         setConversation({
           ...convo,
-          parentMessageId: parentMessageId || null,
+          parentMessageId,
           jailbreakConversationId,
           conversationSignature,
           clientId,
diff --git a/client/src/components/Conversations/index.jsx b/client/src/components/Conversations/index.jsx
index ab49d68b75..13b1e64b00 100644
--- a/client/src/components/Conversations/index.jsx
+++ b/client/src/components/Conversations/index.jsx
@@ -16,6 +16,7 @@ export default function Conversations({ conversations, conversationId, showMore
             ? {
                 jailbreakConversationId: convo.jailbreakConversationId,
                 conversationSignature: convo.conversationSignature,
+                parentMessageId: convo.parentMessageId || null,
                 clientId: convo.clientId,
                 invocationId: convo.invocationId
               }
diff --git a/client/src/components/Main/TextChat.jsx b/client/src/components/Main/TextChat.jsx
index a162a452d2..2350c68e5d 100644
--- a/client/src/components/Main/TextChat.jsx
+++ b/client/src/components/Main/TextChat.jsx
@@ -68,11 +68,30 @@ export default function TextChat({ messages }) {
           })
         );
       } else if (
-        isBing &&
+        model === 'bingai' &&
         convo.conversationId === null &&
         convo.invocationId === null
       ) {
         console.log('Bing data:', data)
+        const {
+          title,
+          conversationSignature,
+          clientId,
+          conversationId,
+          invocationId
+        } = data;
+        dispatch(
+          setConversation({
+            title,
+            parentMessageId: null,
+            conversationSignature,
+            clientId,
+            conversationId,
+            invocationId,
+          })
+        );
+      } else if (model === 'sydney') {
+        console.log('Sydney data:', data)
         const {
           title,
           jailbreakConversationId,
@@ -86,7 +105,7 @@ export default function TextChat({ messages }) {
           setConversation({
             title,
             jailbreakConversationId,
-            parentMessageId: parentMessageId || null,
+            parentMessageId,
             conversationSignature,
             clientId,
             conversationId,