diff --git a/src/background/apis/bing-web.mjs b/src/background/apis/bing-web.mjs
index 5dddb14e..c4f0c5f3 100644
--- a/src/background/apis/bing-web.mjs
+++ b/src/background/apis/bing-web.mjs
@@ -10,6 +10,7 @@ import { pushRecord, setAbortController } from './shared.mjs'
  */
 export async function generateAnswersWithBingWebApi(port, question, session, accessToken) {
   const { controller, messageListener } = setAbortController(port)
+  const config = await getUserConfig()
 
   const bingAIClient = new BingAIClient({ userToken: accessToken })
 
@@ -17,7 +18,8 @@ export async function generateAnswersWithBingWebApi(port, question, session, acc
   const response = await bingAIClient
     .sendMessage(question, {
       abortController: controller,
-      toneStyle: (await getUserConfig()).modelMode,
+      toneStyle: config.modelMode,
+      jailbreakConversationId: config.sydneyMode,
       onProgress: (token) => {
         answer += token
         // remove reference markers [^number^]
diff --git a/src/background/clients/BingAIClient.js b/src/background/clients/BingAIClient.js
index 46cfe5ba..859aa32c 100644
--- a/src/background/clients/BingAIClient.js
+++ b/src/background/clients/BingAIClient.js
@@ -317,8 +317,8 @@ export default class BingAIClient {
           isStartOfSession: invocationId === 0,
           message: {
             author: 'user',
-            text: jailbreakConversationId ? 'Continue the conversation' : message,
-            messageType: 'SearchQuery',
+            text: jailbreakConversationId ? '' : message,
+            messageType: jailbreakConversationId ? 'SearchQuery' : 'Chat',
           },
           conversationSignature,
           participant: {