diff --git a/core/src/types/message/messageEntity.ts b/core/src/types/message/messageEntity.ts
index ba3399b24..a74f059a0 100644
--- a/core/src/types/message/messageEntity.ts
+++ b/core/src/types/message/messageEntity.ts
@@ -59,6 +59,8 @@ export enum MessageStatus {
   Ready = 'ready',
   /** Message is not fully loaded. **/
   Pending = 'pending',
+  /** Message loaded with error. **/
+  Error = 'error',
 }
 
 /**
diff --git a/extensions/inference-nitro-extension/src/index.ts b/extensions/inference-nitro-extension/src/index.ts
index 4aa15a7a9..946d526dd 100644
--- a/extensions/inference-nitro-extension/src/index.ts
+++ b/extensions/inference-nitro-extension/src/index.ts
@@ -223,12 +223,14 @@ export default class JanInferenceNitroExtension implements InferenceExtension {
         events.emit(EventName.OnMessageUpdate, message);
       },
       complete: async () => {
-        message.status = MessageStatus.Ready;
+        message.status = message.content.length
+          ? MessageStatus.Ready
+          : MessageStatus.Error;
         events.emit(EventName.OnMessageUpdate, message);
       },
       error: async (err) => {
-        if (instance.isCancelled || message.content.length > 0) {
-          message.status = MessageStatus.Ready;
+        if (instance.isCancelled || message.content.length) {
+          message.status = MessageStatus.Error;
           events.emit(EventName.OnMessageUpdate, message);
           return;
         }
diff --git a/extensions/inference-openai-extension/src/index.ts b/extensions/inference-openai-extension/src/index.ts
index 64c429664..0f3a5064d 100644
--- a/extensions/inference-openai-extension/src/index.ts
+++ b/extensions/inference-openai-extension/src/index.ts
@@ -213,12 +213,14 @@ export default class JanInferenceOpenAIExtension implements InferenceExtension {
         events.emit(EventName.OnMessageUpdate, message);
       },
       complete: async () => {
-        message.status = MessageStatus.Ready;
+        message.status = message.content.length
+          ? MessageStatus.Ready
+          : MessageStatus.Error;
         events.emit(EventName.OnMessageUpdate, message);
       },
       error: async (err) => {
         if (instance.isCancelled || message.content.length > 0) {
-          message.status = MessageStatus.Ready;
+          message.status = MessageStatus.Error;
           events.emit(EventName.OnMessageUpdate, message);
           return;
         }
diff --git a/extensions/inference-triton-trtllm-extension/src/index.ts b/extensions/inference-triton-trtllm-extension/src/index.ts
index 103d61f68..0720ed3ac 100644
--- a/extensions/inference-triton-trtllm-extension/src/index.ts
+++ b/extensions/inference-triton-trtllm-extension/src/index.ts
@@ -237,10 +237,17 @@ export default class JanInferenceTritonTrtLLMExtension
         events.emit(EventName.OnMessageUpdate, message);
       },
       complete: async () => {
-        message.status = MessageStatus.Ready;
+        message.status = message.content.length
+          ? MessageStatus.Ready
+          : MessageStatus.Error;
         events.emit(EventName.OnMessageUpdate, message);
       },
       error: async (err) => {
+        if (instance.isCancelled || message.content.length) {
+          message.status = MessageStatus.Error;
+          events.emit(EventName.OnMessageUpdate, message);
+          return;
+        }
         const messageContent: ThreadContent = {
           type: ContentType.Text,
           text: {
diff --git a/web/containers/Providers/EventHandler.tsx b/web/containers/Providers/EventHandler.tsx
index 2502340ba..a828a02a1 100644
--- a/web/containers/Providers/EventHandler.tsx
+++ b/web/containers/Providers/EventHandler.tsx
@@ -92,7 +92,10 @@ export default function EventHandler({ children }: { children: ReactNode }) {
       message.content,
       message.status
     )
-    if (message.status === MessageStatus.Ready) {
+    if (
+      message.status === MessageStatus.Ready ||
+      message.status === MessageStatus.Error
+    ) {
       // Mark the thread as not waiting for response
       updateThreadWaiting(message.thread_id, false)
 
diff --git a/web/hooks/useSetActiveThread.ts b/web/hooks/useSetActiveThread.ts
index 0705901c3..65618c7fa 100644
--- a/web/hooks/useSetActiveThread.ts
+++ b/web/hooks/useSetActiveThread.ts
@@ -1,4 +1,4 @@
-import { ExtensionType, Thread } from '@janhq/core'
+import { EventName, ExtensionType, Thread, events } from '@janhq/core'
 
 import { ConversationalExtension } from '@janhq/core'
 
@@ -22,6 +22,8 @@ export default function useSetActiveThread() {
       return
     }
 
+    events.emit(EventName.OnInferenceStopped, thread.id)
+
     // load the corresponding messages
     const messages = await extensionManager
       .get<ConversationalExtension>(ExtensionType.Conversational)
diff --git a/web/screens/Chat/ChatBody/index.tsx b/web/screens/Chat/ChatBody/index.tsx
index 27f3eb8e6..2129c2554 100644
--- a/web/screens/Chat/ChatBody/index.tsx
+++ b/web/screens/Chat/ChatBody/index.tsx
@@ -2,9 +2,17 @@ import { Fragment } from 'react'
 
 import ScrollToBottom from 'react-scroll-to-bottom'
 
-import { InferenceEngine } from '@janhq/core'
+import {
+  ChatCompletionRole,
+  ConversationalExtension,
+  ExtensionType,
+  InferenceEngine,
+  MessageStatus,
+} from '@janhq/core'
 import { Button } from '@janhq/uikit'
-import { useAtomValue } from 'jotai'
+import { useAtomValue, useSetAtom } from 'jotai'
+
+import { RefreshCcw } from 'lucide-react'
 
 import LogoMark from '@/containers/Brand/Logo/Mark'
 
@@ -14,14 +22,45 @@ import { useGetDownloadedModels } from '@/hooks/useGetDownloadedModels'
 
 import { useMainViewState } from '@/hooks/useMainViewState'
 
+import useSendChatMessage from '@/hooks/useSendChatMessage'
+
 import ChatItem from '../ChatItem'
 
-import { getCurrentChatMessagesAtom } from '@/helpers/atoms/ChatMessage.atom'
+import { extensionManager } from '@/extension'
+import {
+  deleteMessageAtom,
+  getCurrentChatMessagesAtom,
+} from '@/helpers/atoms/ChatMessage.atom'
+import { activeThreadAtom } from '@/helpers/atoms/Thread.atom'
 
 const ChatBody: React.FC = () => {
   const messages = useAtomValue(getCurrentChatMessagesAtom)
   const { downloadedModels } = useGetDownloadedModels()
   const { setMainViewState } = useMainViewState()
+  const thread = useAtomValue(activeThreadAtom)
+  const deleteMessage = useSetAtom(deleteMessageAtom)
+  const { resendChatMessage } = useSendChatMessage()
+
+  const regenerateMessage = async () => {
+    const lastMessageIndex = messages.length - 1
+    const message = messages[lastMessageIndex]
+    if (message.role !== ChatCompletionRole.User) {
+      // Delete last response before regenerating
+      deleteMessage(message.id ?? '')
+      if (thread) {
+        await extensionManager
+          .get<ConversationalExtension>(ExtensionType.Conversational)
+          ?.writeMessages(
+            thread.id,
+            messages.filter((msg) => msg.id !== message.id)
+          )
+      }
+      const targetMessage = messages[lastMessageIndex - 1]
+      if (targetMessage) resendChatMessage(targetMessage)
+    } else {
+      resendChatMessage(message)
+    }
+  }
 
   if (downloadedModels.length === 0)
     return (
@@ -76,8 +115,35 @@ const ChatBody: React.FC = () => {
         </div>
       ) : (
         <ScrollToBottom className="flex h-full w-full flex-col">
-          {messages.map((message) => (
-            <ChatItem {...message} key={message.id} />
+          {messages.map((message, index) => (
+            <>
+              {message.content.length ? (
+                <ChatItem {...message} key={message.id} />
+              ) : (
+                <></>
+              )}
+              {message.status === MessageStatus.Error &&
+                index === messages.length - 1 && (
+                  <div
+                    key={message.id}
+                    className="mt-10 flex flex-col items-center"
+                  >
+                    <span className="mb-3 text-center text-sm font-medium text-gray-500">
+                      Whoops! Jan&apos;s generation was interrupted. Let&apos;s
+                      give it another go!
+                    </span>
+                    <Button
+                      className="w-min"
+                      themes="outline"
+                      onClick={regenerateMessage}
+                    >
+                      <RefreshCcw size={14} className="" />
+                      <span className="w-2" />
+                      Regenerate
+                    </Button>
+                  </div>
+                )}
+            </>
           ))}
         </ScrollToBottom>
       )}
diff --git a/web/screens/Chat/MessageToolbar/index.tsx b/web/screens/Chat/MessageToolbar/index.tsx
index 87004cc3b..721b0476b 100644
--- a/web/screens/Chat/MessageToolbar/index.tsx
+++ b/web/screens/Chat/MessageToolbar/index.tsx
@@ -47,19 +47,20 @@ const MessageToolbar = ({ message }: { message: ThreadMessage }) => {
     resendChatMessage(message)
   }
 
-  if (message.status !== MessageStatus.Ready) return null
+  if (message.status === MessageStatus.Pending) return null
 
   return (
     <div className={twMerge('flex flex-row items-center')}>
       <div className="flex overflow-hidden rounded-md border border-border bg-background/20">
-        {message.id === messages[messages.length - 1]?.id && (
-          <div
-            className="cursor-pointer border-r border-border px-2 py-2 hover:bg-background/80"
-            onClick={onRegenerateClick}
-          >
-            <RefreshCcw size={14} />
-          </div>
-        )}
+        {message.id === messages[messages.length - 1]?.id &&
+          messages[messages.length - 1].status !== MessageStatus.Error && (
+            <div
+              className="cursor-pointer border-r border-border px-2 py-2 hover:bg-background/80"
+              onClick={onRegenerateClick}
+            >
+              <RefreshCcw size={14} />
+            </div>
+          )}
         <div
           className="cursor-pointer border-r border-border px-2 py-2 hover:bg-background/80"
           onClick={() => {
diff --git a/web/screens/Chat/SimpleTextMessage/index.tsx b/web/screens/Chat/SimpleTextMessage/index.tsx
index e9107d6af..75ce5b24a 100644
--- a/web/screens/Chat/SimpleTextMessage/index.tsx
+++ b/web/screens/Chat/SimpleTextMessage/index.tsx
@@ -99,7 +99,10 @@ const SimpleTextMessage: React.FC<ThreadMessage> = (props) => {
   }, [])
 
   useEffect(() => {
-    if (props.status === MessageStatus.Ready) {
+    if (
+      props.status === MessageStatus.Ready ||
+      props.status === MessageStatus.Error
+    ) {
       return
     }
     const currentTimestamp = new Date().getTime() // Get current time in milliseconds