diff --git a/README.md b/README.md
index 5ef41deac..994a494f9 100644
--- a/README.md
+++ b/README.md
@@ -61,6 +61,7 @@ bolt.diy was originally started by [Cole Medin](https://www.youtube.com/@ColeMed
 - ✅ PromptLibrary to have different variations of prompts for different use cases (@thecodacus)
 - ✅ Detect package.json and commands to auto install & run preview for folder and git import (@wonderwhy-er)
 - ✅ Selection tool to target changes visually (@emcconnell)
+- ✅ Detect terminal Errors and ask bolt to fix it (@thecodacus)
 - ⬜ **HIGH PRIORITY** - Prevent bolt from rewriting files as often (file locking and diffs)
 - ⬜ **HIGH PRIORITY** - Better prompting for smaller LLMs (code window sometimes doesn't start)
 - ⬜ **HIGH PRIORITY** - Run agents in the backend as opposed to a single model call
diff --git a/app/components/chat/BaseChat.tsx b/app/components/chat/BaseChat.tsx
index 7c2a9da12..422c6e469 100644
--- a/app/components/chat/BaseChat.tsx
+++ b/app/components/chat/BaseChat.tsx
@@ -28,6 +28,8 @@ import { SpeechRecognitionButton } from '~/components/chat/SpeechRecognition';
 import type { IProviderSetting, ProviderInfo } from '~/types/model';
 import { ScreenshotStateManager } from './ScreenshotStateManager';
 import { toast } from 'react-toastify';
+import type { ActionAlert } from '~/types/actions';
+import ChatAlert from './ChatAlert';
 
 const TEXTAREA_MIN_HEIGHT = 76;
 
@@ -58,6 +60,8 @@ interface BaseChatProps {
   setUploadedFiles?: (files: File[]) => void;
   imageDataList?: string[];
   setImageDataList?: (dataList: string[]) => void;
+  actionAlert?: ActionAlert;
+  clearAlert?: () => void;
 }
 
 export const BaseChat = React.forwardRef<HTMLDivElement, BaseChatProps>(
@@ -89,6 +93,8 @@ export const BaseChat = React.forwardRef<HTMLDivElement, BaseChatProps>(
       imageDataList = [],
       setImageDataList,
       messages,
+      actionAlert,
+      clearAlert,
     },
     ref,
   ) => {
@@ -318,226 +324,247 @@ export const BaseChat = React.forwardRef<HTMLDivElement, BaseChatProps>(
                 }}
               </ClientOnly>
               <div
-                className={classNames(
-                  'bg-bolt-elements-background-depth-2 p-3 rounded-lg border border-bolt-elements-borderColor relative w-full max-w-chat mx-auto z-prompt mb-6',
-                  {
-                    'sticky bottom-2': chatStarted,
-                  },
-                )}
+                className={classNames('flex flex-col gap-4 w-full max-w-chat mx-auto z-prompt mb-6', {
+                  'sticky bottom-2': chatStarted,
+                })}
               >
-                <svg className={classNames(styles.PromptEffectContainer)}>
-                  <defs>
-                    <linearGradient
-                      id="line-gradient"
-                      x1="20%"
-                      y1="0%"
-                      x2="-14%"
-                      y2="10%"
-                      gradientUnits="userSpaceOnUse"
-                      gradientTransform="rotate(-45)"
-                    >
-                      <stop offset="0%" stopColor="#b44aff" stopOpacity="0%"></stop>
-                      <stop offset="40%" stopColor="#b44aff" stopOpacity="80%"></stop>
-                      <stop offset="50%" stopColor="#b44aff" stopOpacity="80%"></stop>
-                      <stop offset="100%" stopColor="#b44aff" stopOpacity="0%"></stop>
-                    </linearGradient>
-                    <linearGradient id="shine-gradient">
-                      <stop offset="0%" stopColor="white" stopOpacity="0%"></stop>
-                      <stop offset="40%" stopColor="#ffffff" stopOpacity="80%"></stop>
-                      <stop offset="50%" stopColor="#ffffff" stopOpacity="80%"></stop>
-                      <stop offset="100%" stopColor="white" stopOpacity="0%"></stop>
-                    </linearGradient>
-                  </defs>
-                  <rect className={classNames(styles.PromptEffectLine)} pathLength="100" strokeLinecap="round"></rect>
-                  <rect className={classNames(styles.PromptShine)} x="48" y="24" width="70" height="1"></rect>
-                </svg>
-                <div>
-                  <div className={isModelSettingsCollapsed ? 'hidden' : ''}>
-                    <ModelSelector
-                      key={provider?.name + ':' + modelList.length}
-                      model={model}
-                      setModel={setModel}
-                      modelList={modelList}
-                      provider={provider}
-                      setProvider={setProvider}
-                      providerList={providerList || (PROVIDER_LIST as ProviderInfo[])}
-                      apiKeys={apiKeys}
-                    />
-                    {(providerList || []).length > 0 && provider && (
-                      <APIKeyManager
-                        provider={provider}
-                        apiKey={apiKeys[provider.name] || ''}
-                        setApiKey={(key) => {
-                          const newApiKeys = { ...apiKeys, [provider.name]: key };
-                          setApiKeys(newApiKeys);
-                          Cookies.set('apiKeys', JSON.stringify(newApiKeys));
-                        }}
-                      />
-                    )}
-                  </div>
-                </div>
-                <FilePreview
-                  files={uploadedFiles}
-                  imageDataList={imageDataList}
-                  onRemove={(index) => {
-                    setUploadedFiles?.(uploadedFiles.filter((_, i) => i !== index));
-                    setImageDataList?.(imageDataList.filter((_, i) => i !== index));
-                  }}
-                />
-                <ClientOnly>
-                  {() => (
-                    <ScreenshotStateManager
-                      setUploadedFiles={setUploadedFiles}
-                      setImageDataList={setImageDataList}
-                      uploadedFiles={uploadedFiles}
-                      imageDataList={imageDataList}
+                <div className="bg-bolt-elements-background-depth-2">
+                  {actionAlert && (
+                    <ChatAlert
+                      alert={actionAlert}
+                      clearAlert={() => clearAlert?.()}
+                      postMessage={(message) => {
+                        sendMessage?.({} as any, message);
+                        clearAlert?.();
+                      }}
                     />
                   )}
-                </ClientOnly>
+                </div>
                 <div
                   className={classNames(
-                    'relative shadow-xs border border-bolt-elements-borderColor backdrop-blur rounded-lg',
+                    'bg-bolt-elements-background-depth-2 p-3 rounded-lg border border-bolt-elements-borderColor relative w-full max-w-chat mx-auto z-prompt',
+
+                    /*
+                     * {
+                     *   'sticky bottom-2': chatStarted,
+                     * },
+                     */
                   )}
                 >
-                  <textarea
-                    ref={textareaRef}
-                    className={classNames(
-                      'w-full pl-4 pt-4 pr-16 outline-none resize-none text-bolt-elements-textPrimary placeholder-bolt-elements-textTertiary bg-transparent text-sm',
-                      'transition-all duration-200',
-                      'hover:border-bolt-elements-focus',
-                    )}
-                    onDragEnter={(e) => {
-                      e.preventDefault();
-                      e.currentTarget.style.border = '2px solid #1488fc';
-                    }}
-                    onDragOver={(e) => {
-                      e.preventDefault();
-                      e.currentTarget.style.border = '2px solid #1488fc';
-                    }}
-                    onDragLeave={(e) => {
-                      e.preventDefault();
-                      e.currentTarget.style.border = '1px solid var(--bolt-elements-borderColor)';
-                    }}
-                    onDrop={(e) => {
-                      e.preventDefault();
-                      e.currentTarget.style.border = '1px solid var(--bolt-elements-borderColor)';
-
-                      const files = Array.from(e.dataTransfer.files);
-                      files.forEach((file) => {
-                        if (file.type.startsWith('image/')) {
-                          const reader = new FileReader();
-
-                          reader.onload = (e) => {
-                            const base64Image = e.target?.result as string;
-                            setUploadedFiles?.([...uploadedFiles, file]);
-                            setImageDataList?.([...imageDataList, base64Image]);
-                          };
-                          reader.readAsDataURL(file);
-                        }
-                      });
-                    }}
-                    onKeyDown={(event) => {
-                      if (event.key === 'Enter') {
-                        if (event.shiftKey) {
-                          return;
-                        }
-
-                        event.preventDefault();
-
-                        if (isStreaming) {
-                          handleStop?.();
-                          return;
-                        }
-
-                        // ignore if using input method engine
-                        if (event.nativeEvent.isComposing) {
-                          return;
-                        }
-
-                        handleSendMessage?.(event);
-                      }
-                    }}
-                    value={input}
-                    onChange={(event) => {
-                      handleInputChange?.(event);
-                    }}
-                    onPaste={handlePaste}
-                    style={{
-                      minHeight: TEXTAREA_MIN_HEIGHT,
-                      maxHeight: TEXTAREA_MAX_HEIGHT,
+                  <svg className={classNames(styles.PromptEffectContainer)}>
+                    <defs>
+                      <linearGradient
+                        id="line-gradient"
+                        x1="20%"
+                        y1="0%"
+                        x2="-14%"
+                        y2="10%"
+                        gradientUnits="userSpaceOnUse"
+                        gradientTransform="rotate(-45)"
+                      >
+                        <stop offset="0%" stopColor="#b44aff" stopOpacity="0%"></stop>
+                        <stop offset="40%" stopColor="#b44aff" stopOpacity="80%"></stop>
+                        <stop offset="50%" stopColor="#b44aff" stopOpacity="80%"></stop>
+                        <stop offset="100%" stopColor="#b44aff" stopOpacity="0%"></stop>
+                      </linearGradient>
+                      <linearGradient id="shine-gradient">
+                        <stop offset="0%" stopColor="white" stopOpacity="0%"></stop>
+                        <stop offset="40%" stopColor="#ffffff" stopOpacity="80%"></stop>
+                        <stop offset="50%" stopColor="#ffffff" stopOpacity="80%"></stop>
+                        <stop offset="100%" stopColor="white" stopOpacity="0%"></stop>
+                      </linearGradient>
+                    </defs>
+                    <rect className={classNames(styles.PromptEffectLine)} pathLength="100" strokeLinecap="round"></rect>
+                    <rect className={classNames(styles.PromptShine)} x="48" y="24" width="70" height="1"></rect>
+                  </svg>
+                  <div>
+                    <div className={isModelSettingsCollapsed ? 'hidden' : ''}>
+                      <ModelSelector
+                        key={provider?.name + ':' + modelList.length}
+                        model={model}
+                        setModel={setModel}
+                        modelList={modelList}
+                        provider={provider}
+                        setProvider={setProvider}
+                        providerList={providerList || (PROVIDER_LIST as ProviderInfo[])}
+                        apiKeys={apiKeys}
+                      />
+                      {(providerList || []).length > 0 && provider && (
+                        <APIKeyManager
+                          provider={provider}
+                          apiKey={apiKeys[provider.name] || ''}
+                          setApiKey={(key) => {
+                            const newApiKeys = { ...apiKeys, [provider.name]: key };
+                            setApiKeys(newApiKeys);
+                            Cookies.set('apiKeys', JSON.stringify(newApiKeys));
+                          }}
+                        />
+                      )}
+                    </div>
+                  </div>
+                  <FilePreview
+                    files={uploadedFiles}
+                    imageDataList={imageDataList}
+                    onRemove={(index) => {
+                      setUploadedFiles?.(uploadedFiles.filter((_, i) => i !== index));
+                      setImageDataList?.(imageDataList.filter((_, i) => i !== index));
                     }}
-                    placeholder="How can Bolt help you today?"
-                    translate="no"
                   />
                   <ClientOnly>
                     {() => (
-                      <SendButton
-                        show={input.length > 0 || isStreaming || uploadedFiles.length > 0}
-                        isStreaming={isStreaming}
-                        disabled={!providerList || providerList.length === 0}
-                        onClick={(event) => {
+                      <ScreenshotStateManager
+                        setUploadedFiles={setUploadedFiles}
+                        setImageDataList={setImageDataList}
+                        uploadedFiles={uploadedFiles}
+                        imageDataList={imageDataList}
+                      />
+                    )}
+                  </ClientOnly>
+                  <div
+                    className={classNames(
+                      'relative shadow-xs border border-bolt-elements-borderColor backdrop-blur rounded-lg',
+                    )}
+                  >
+                    <textarea
+                      ref={textareaRef}
+                      className={classNames(
+                        'w-full pl-4 pt-4 pr-16 outline-none resize-none text-bolt-elements-textPrimary placeholder-bolt-elements-textTertiary bg-transparent text-sm',
+                        'transition-all duration-200',
+                        'hover:border-bolt-elements-focus',
+                      )}
+                      onDragEnter={(e) => {
+                        e.preventDefault();
+                        e.currentTarget.style.border = '2px solid #1488fc';
+                      }}
+                      onDragOver={(e) => {
+                        e.preventDefault();
+                        e.currentTarget.style.border = '2px solid #1488fc';
+                      }}
+                      onDragLeave={(e) => {
+                        e.preventDefault();
+                        e.currentTarget.style.border = '1px solid var(--bolt-elements-borderColor)';
+                      }}
+                      onDrop={(e) => {
+                        e.preventDefault();
+                        e.currentTarget.style.border = '1px solid var(--bolt-elements-borderColor)';
+
+                        const files = Array.from(e.dataTransfer.files);
+                        files.forEach((file) => {
+                          if (file.type.startsWith('image/')) {
+                            const reader = new FileReader();
+
+                            reader.onload = (e) => {
+                              const base64Image = e.target?.result as string;
+                              setUploadedFiles?.([...uploadedFiles, file]);
+                              setImageDataList?.([...imageDataList, base64Image]);
+                            };
+                            reader.readAsDataURL(file);
+                          }
+                        });
+                      }}
+                      onKeyDown={(event) => {
+                        if (event.key === 'Enter') {
+                          if (event.shiftKey) {
+                            return;
+                          }
+
+                          event.preventDefault();
+
                           if (isStreaming) {
                             handleStop?.();
                             return;
                           }
 
-                          if (input.length > 0 || uploadedFiles.length > 0) {
-                            handleSendMessage?.(event);
+                          // ignore if using input method engine
+                          if (event.nativeEvent.isComposing) {
+                            return;
                           }
-                        }}
-                      />
-                    )}
-                  </ClientOnly>
-                  <div className="flex justify-between items-center text-sm p-4 pt-2">
-                    <div className="flex gap-1 items-center">
-                      <IconButton title="Upload file" className="transition-all" onClick={() => handleFileUpload()}>
-                        <div className="i-ph:paperclip text-xl"></div>
-                      </IconButton>
-                      <IconButton
-                        title="Enhance prompt"
-                        disabled={input.length === 0 || enhancingPrompt}
-                        className={classNames('transition-all', enhancingPrompt ? 'opacity-100' : '')}
-                        onClick={() => {
-                          enhancePrompt?.();
-                          toast.success('Prompt enhanced!');
-                        }}
-                      >
-                        {enhancingPrompt ? (
-                          <div className="i-svg-spinners:90-ring-with-bg text-bolt-elements-loader-progress text-xl animate-spin"></div>
-                        ) : (
-                          <div className="i-bolt:stars text-xl"></div>
-                        )}
-                      </IconButton>
-
-                      <SpeechRecognitionButton
-                        isListening={isListening}
-                        onStart={startListening}
-                        onStop={stopListening}
-                        disabled={isStreaming}
-                      />
-                      {chatStarted && <ClientOnly>{() => <ExportChatButton exportChat={exportChat} />}</ClientOnly>}
-                      <IconButton
-                        title="Model Settings"
-                        className={classNames('transition-all flex items-center gap-1', {
-                          'bg-bolt-elements-item-backgroundAccent text-bolt-elements-item-contentAccent':
-                            isModelSettingsCollapsed,
-                          'bg-bolt-elements-item-backgroundDefault text-bolt-elements-item-contentDefault':
-                            !isModelSettingsCollapsed,
-                        })}
-                        onClick={() => setIsModelSettingsCollapsed(!isModelSettingsCollapsed)}
-                        disabled={!providerList || providerList.length === 0}
-                      >
-                        <div className={`i-ph:caret-${isModelSettingsCollapsed ? 'right' : 'down'} text-lg`} />
-                        {isModelSettingsCollapsed ? <span className="text-xs">{model}</span> : <span />}
-                      </IconButton>
-                    </div>
-                    {input.length > 3 ? (
-                      <div className="text-xs text-bolt-elements-textTertiary">
-                        Use <kbd className="kdb px-1.5 py-0.5 rounded bg-bolt-elements-background-depth-2">Shift</kbd> +{' '}
-                        <kbd className="kdb px-1.5 py-0.5 rounded bg-bolt-elements-background-depth-2">Return</kbd> a
-                        new line
+
+                          handleSendMessage?.(event);
+                        }
+                      }}
+                      value={input}
+                      onChange={(event) => {
+                        handleInputChange?.(event);
+                      }}
+                      onPaste={handlePaste}
+                      style={{
+                        minHeight: TEXTAREA_MIN_HEIGHT,
+                        maxHeight: TEXTAREA_MAX_HEIGHT,
+                      }}
+                      placeholder="How can Bolt help you today?"
+                      translate="no"
+                    />
+                    <ClientOnly>
+                      {() => (
+                        <SendButton
+                          show={input.length > 0 || isStreaming || uploadedFiles.length > 0}
+                          isStreaming={isStreaming}
+                          disabled={!providerList || providerList.length === 0}
+                          onClick={(event) => {
+                            if (isStreaming) {
+                              handleStop?.();
+                              return;
+                            }
+
+                            if (input.length > 0 || uploadedFiles.length > 0) {
+                              handleSendMessage?.(event);
+                            }
+                          }}
+                        />
+                      )}
+                    </ClientOnly>
+                    <div className="flex justify-between items-center text-sm p-4 pt-2">
+                      <div className="flex gap-1 items-center">
+                        <IconButton title="Upload file" className="transition-all" onClick={() => handleFileUpload()}>
+                          <div className="i-ph:paperclip text-xl"></div>
+                        </IconButton>
+                        <IconButton
+                          title="Enhance prompt"
+                          disabled={input.length === 0 || enhancingPrompt}
+                          className={classNames('transition-all', enhancingPrompt ? 'opacity-100' : '')}
+                          onClick={() => {
+                            enhancePrompt?.();
+                            toast.success('Prompt enhanced!');
+                          }}
+                        >
+                          {enhancingPrompt ? (
+                            <div className="i-svg-spinners:90-ring-with-bg text-bolt-elements-loader-progress text-xl animate-spin"></div>
+                          ) : (
+                            <div className="i-bolt:stars text-xl"></div>
+                          )}
+                        </IconButton>
+
+                        <SpeechRecognitionButton
+                          isListening={isListening}
+                          onStart={startListening}
+                          onStop={stopListening}
+                          disabled={isStreaming}
+                        />
+                        {chatStarted && <ClientOnly>{() => <ExportChatButton exportChat={exportChat} />}</ClientOnly>}
+                        <IconButton
+                          title="Model Settings"
+                          className={classNames('transition-all flex items-center gap-1', {
+                            'bg-bolt-elements-item-backgroundAccent text-bolt-elements-item-contentAccent':
+                              isModelSettingsCollapsed,
+                            'bg-bolt-elements-item-backgroundDefault text-bolt-elements-item-contentDefault':
+                              !isModelSettingsCollapsed,
+                          })}
+                          onClick={() => setIsModelSettingsCollapsed(!isModelSettingsCollapsed)}
+                          disabled={!providerList || providerList.length === 0}
+                        >
+                          <div className={`i-ph:caret-${isModelSettingsCollapsed ? 'right' : 'down'} text-lg`} />
+                          {isModelSettingsCollapsed ? <span className="text-xs">{model}</span> : <span />}
+                        </IconButton>
                       </div>
-                    ) : null}
+                      {input.length > 3 ? (
+                        <div className="text-xs text-bolt-elements-textTertiary">
+                          Use <kbd className="kdb px-1.5 py-0.5 rounded bg-bolt-elements-background-depth-2">Shift</kbd>{' '}
+                          + <kbd className="kdb px-1.5 py-0.5 rounded bg-bolt-elements-background-depth-2">Return</kbd>{' '}
+                          a new line
+                        </div>
+                      ) : null}
+                    </div>
                   </div>
                 </div>
               </div>
diff --git a/app/components/chat/Chat.client.tsx b/app/components/chat/Chat.client.tsx
index 1b830fd90..b78348240 100644
--- a/app/components/chat/Chat.client.tsx
+++ b/app/components/chat/Chat.client.tsx
@@ -35,6 +35,9 @@ export function Chat() {
 
   const { ready, initialMessages, storeMessageHistory, importChat, exportChat } = useChatHistory();
   const title = useStore(description);
+  useEffect(() => {
+    workbenchStore.setReloadedMessages(initialMessages.map((m) => m.id));
+  }, [initialMessages]);
 
   return (
     <>
@@ -114,6 +117,7 @@ export const ChatImpl = memo(
     const [imageDataList, setImageDataList] = useState<string[]>([]); // Move here
     const [searchParams, setSearchParams] = useSearchParams();
     const files = useStore(workbenchStore.files);
+    const actionAlert = useStore(workbenchStore.alert);
     const { activeProviders, promptId } = useSettings();
 
     const [model, setModel] = useState(() => {
@@ -408,6 +412,8 @@ export const ChatImpl = memo(
         setUploadedFiles={setUploadedFiles}
         imageDataList={imageDataList}
         setImageDataList={setImageDataList}
+        actionAlert={actionAlert}
+        clearAlert={() => workbenchStore.clearAlert()}
       />
     );
   },
diff --git a/app/components/chat/ChatAlert.tsx b/app/components/chat/ChatAlert.tsx
new file mode 100644
index 000000000..21c12b775
--- /dev/null
+++ b/app/components/chat/ChatAlert.tsx
@@ -0,0 +1,102 @@
+import { AnimatePresence, motion } from 'framer-motion';
+import type { ActionAlert } from '~/types/actions';
+import { classNames } from '~/utils/classNames';
+
+interface Props {
+  alert: ActionAlert;
+  clearAlert: () => void;
+  postMessage: (message: string) => void;
+}
+
+export default function ChatAlert({ alert, clearAlert, postMessage }: Props) {
+  const { description, content } = alert;
+
+  return (
+    <AnimatePresence>
+      <motion.div
+        initial={{ opacity: 0, y: -20 }}
+        animate={{ opacity: 1, y: 0 }}
+        exit={{ opacity: 0, y: -20 }}
+        transition={{ duration: 0.3 }}
+        className={`rounded-lg border border-bolt-elements-borderColor bg-bolt-elements-background-depth-2 p-4`}
+      >
+        <div className="flex items-start">
+          {/* Icon */}
+          <motion.div
+            className="flex-shrink-0"
+            initial={{ scale: 0 }}
+            animate={{ scale: 1 }}
+            transition={{ delay: 0.2 }}
+          >
+            <div className={`i-ph:warning-duotone text-xl text-bolt-elements-button-danger-text`}></div>
+          </motion.div>
+          {/* Content */}
+          <div className="ml-3 flex-1">
+            <motion.h3
+              initial={{ opacity: 0 }}
+              animate={{ opacity: 1 }}
+              transition={{ delay: 0.1 }}
+              className={`text-sm font-medium text-bolt-elements-textPrimary`}
+            >
+              {/* {title} */}
+              Opps There is an error
+            </motion.h3>
+            <motion.div
+              initial={{ opacity: 0 }}
+              animate={{ opacity: 1 }}
+              transition={{ delay: 0.2 }}
+              className={`mt-2 text-sm text-bolt-elements-textSecondary`}
+            >
+              <p>
+                We encountered an error while running terminal commands. Would you like Bolt to analyze and help resolve
+                this issue?
+              </p>
+              {description && (
+                <div className="text-xs text-bolt-elements-textSecondary p-2 bg-bolt-elements-background-depth-3 rounded mt-4 mb-4">
+                  Error: {description}
+                </div>
+              )}
+            </motion.div>
+
+            {/* Actions */}
+            <motion.div
+              className="mt-4"
+              initial={{ opacity: 0, y: 10 }}
+              animate={{ opacity: 1, y: 0 }}
+              transition={{ delay: 0.3 }}
+            >
+              <div className={classNames(' flex gap-2')}>
+                <button
+                  onClick={() => postMessage(`*Fix this error on terminal* \n\`\`\`sh\n${content}\n\`\`\`\n`)}
+                  className={classNames(
+                    `px-2 py-1.5 rounded-md text-sm font-medium`,
+                    'bg-bolt-elements-button-primary-background',
+                    'hover:bg-bolt-elements-button-primary-backgroundHover',
+                    'focus:outline-none focus:ring-2 focus:ring-offset-2 focus:ring-bolt-elements-button-danger-background',
+                    'text-bolt-elements-button-primary-text',
+                    'flex items-center gap-1.5',
+                  )}
+                >
+                  <div className="i-ph:chat-circle-duotone"></div>
+                  Ask Bolt
+                </button>
+                <button
+                  onClick={clearAlert}
+                  className={classNames(
+                    `px-2 py-1.5 rounded-md text-sm font-medium`,
+                    'bg-bolt-elements-button-secondary-background',
+                    'hover:bg-bolt-elements-button-secondary-backgroundHover',
+                    'focus:outline-none focus:ring-2 focus:ring-offset-2 focus:ring-bolt-elements-button-secondary-background',
+                    'text-bolt-elements-button-secondary-text',
+                  )}
+                >
+                  Dismiss
+                </button>
+              </div>
+            </motion.div>
+          </div>
+        </div>
+      </motion.div>
+    </AnimatePresence>
+  );
+}
diff --git a/app/lib/runtime/action-runner.ts b/app/lib/runtime/action-runner.ts
index 0e1d218aa..c7bd29b16 100644
--- a/app/lib/runtime/action-runner.ts
+++ b/app/lib/runtime/action-runner.ts
@@ -1,7 +1,7 @@
 import { WebContainer } from '@webcontainer/api';
 import { atom, map, type MapStore } from 'nanostores';
 import * as nodePath from 'node:path';
-import type { BoltAction } from '~/types/actions';
+import type { ActionAlert, BoltAction } from '~/types/actions';
 import { createScopedLogger } from '~/utils/logger';
 import { unreachable } from '~/utils/unreachable';
 import type { ActionCallbackData } from './message-parser';
@@ -34,16 +34,51 @@ export type ActionStateUpdate =
 
 type ActionsMap = MapStore<Record<string, ActionState>>;
 
+class ActionCommandError extends Error {
+  readonly _output: string;
+  readonly _header: string;
+
+  constructor(message: string, output: string) {
+    // Create a formatted message that includes both the error message and output
+    const formattedMessage = `Failed To Execute Shell Command: ${message}\n\nOutput:\n${output}`;
+    super(formattedMessage);
+
+    // Set the output separately so it can be accessed programmatically
+    this._header = message;
+    this._output = output;
+
+    // Maintain proper prototype chain
+    Object.setPrototypeOf(this, ActionCommandError.prototype);
+
+    // Set the name of the error for better debugging
+    this.name = 'ActionCommandError';
+  }
+
+  // Optional: Add a method to get just the terminal output
+  get output() {
+    return this._output;
+  }
+  get header() {
+    return this._header;
+  }
+}
+
 export class ActionRunner {
   #webcontainer: Promise<WebContainer>;
   #currentExecutionPromise: Promise<void> = Promise.resolve();
   #shellTerminal: () => BoltShell;
   runnerId = atom<string>(`${Date.now()}`);
   actions: ActionsMap = map({});
+  onAlert?: (alert: ActionAlert) => void;
 
-  constructor(webcontainerPromise: Promise<WebContainer>, getShellTerminal: () => BoltShell) {
+  constructor(
+    webcontainerPromise: Promise<WebContainer>,
+    getShellTerminal: () => BoltShell,
+    onAlert?: (alert: ActionAlert) => void,
+  ) {
     this.#webcontainer = webcontainerPromise;
     this.#shellTerminal = getShellTerminal;
+    this.onAlert = onAlert;
   }
 
   addAction(data: ActionCallbackData) {
@@ -126,7 +161,25 @@ export class ActionRunner {
 
           this.#runStartAction(action)
             .then(() => this.#updateAction(actionId, { status: 'complete' }))
-            .catch(() => this.#updateAction(actionId, { status: 'failed', error: 'Action failed' }));
+            .catch((err: Error) => {
+              if (action.abortSignal.aborted) {
+                return;
+              }
+
+              this.#updateAction(actionId, { status: 'failed', error: 'Action failed' });
+              logger.error(`[${action.type}]:Action failed\n\n`, err);
+
+              if (!(err instanceof ActionCommandError)) {
+                return;
+              }
+
+              this.onAlert?.({
+                type: 'error',
+                title: 'Dev Server Failed',
+                description: err.header,
+                content: err.output,
+              });
+            });
 
           /*
            * adding a delay to avoid any race condition between 2 start actions
@@ -142,9 +195,24 @@ export class ActionRunner {
         status: isStreaming ? 'running' : action.abortSignal.aborted ? 'aborted' : 'complete',
       });
     } catch (error) {
+      if (action.abortSignal.aborted) {
+        return;
+      }
+
       this.#updateAction(actionId, { status: 'failed', error: 'Action failed' });
       logger.error(`[${action.type}]:Action failed\n\n`, error);
 
+      if (!(error instanceof ActionCommandError)) {
+        return;
+      }
+
+      this.onAlert?.({
+        type: 'error',
+        title: 'Dev Server Failed',
+        description: error.header,
+        content: error.output,
+      });
+
       // re-throw the error to be caught in the promise chain
       throw error;
     }
@@ -162,11 +230,14 @@ export class ActionRunner {
       unreachable('Shell terminal not found');
     }
 
-    const resp = await shell.executeCommand(this.runnerId.get(), action.content);
+    const resp = await shell.executeCommand(this.runnerId.get(), action.content, () => {
+      logger.debug(`[${action.type}]:Aborting Action\n\n`, action);
+      action.abort();
+    });
     logger.debug(`${action.type} Shell Response: [exit code:${resp?.exitCode}]`);
 
     if (resp?.exitCode != 0) {
-      throw new Error('Failed To Execute Shell Command');
+      throw new ActionCommandError(`Failed To Execute Shell Command`, resp?.output || 'No Output Available');
     }
   }
 
@@ -186,11 +257,14 @@ export class ActionRunner {
       unreachable('Shell terminal not found');
     }
 
-    const resp = await shell.executeCommand(this.runnerId.get(), action.content);
+    const resp = await shell.executeCommand(this.runnerId.get(), action.content, () => {
+      logger.debug(`[${action.type}]:Aborting Action\n\n`, action);
+      action.abort();
+    });
     logger.debug(`${action.type} Shell Response: [exit code:${resp?.exitCode}]`);
 
     if (resp?.exitCode != 0) {
-      throw new Error('Failed To Start Application');
+      throw new ActionCommandError('Failed To Start Application', resp?.output || 'No Output Available');
     }
 
     return resp;
diff --git a/app/lib/stores/workbench.ts b/app/lib/stores/workbench.ts
index 0d46057db..92c3508cd 100644
--- a/app/lib/stores/workbench.ts
+++ b/app/lib/stores/workbench.ts
@@ -17,6 +17,7 @@ import { extractRelativePath } from '~/utils/diff';
 import { description } from '~/lib/persistence';
 import Cookies from 'js-cookie';
 import { createSampler } from '~/utils/sampler';
+import type { ActionAlert } from '~/types/actions';
 
 export interface ArtifactState {
   id: string;
@@ -38,11 +39,15 @@ export class WorkbenchStore {
   #editorStore = new EditorStore(this.#filesStore);
   #terminalStore = new TerminalStore(webcontainer);
 
+  #reloadedMessages = new Set<string>();
+
   artifacts: Artifacts = import.meta.hot?.data.artifacts ?? map({});
 
   showWorkbench: WritableAtom<boolean> = import.meta.hot?.data.showWorkbench ?? atom(false);
   currentView: WritableAtom<WorkbenchViewType> = import.meta.hot?.data.currentView ?? atom('code');
   unsavedFiles: WritableAtom<Set<string>> = import.meta.hot?.data.unsavedFiles ?? atom(new Set<string>());
+  actionAlert: WritableAtom<ActionAlert | undefined> =
+    import.meta.hot?.data.unsavedFiles ?? atom<ActionAlert | undefined>(undefined);
   modifiedFiles = new Set<string>();
   artifactIdList: string[] = [];
   #globalExecutionQueue = Promise.resolve();
@@ -52,6 +57,7 @@ export class WorkbenchStore {
       import.meta.hot.data.unsavedFiles = this.unsavedFiles;
       import.meta.hot.data.showWorkbench = this.showWorkbench;
       import.meta.hot.data.currentView = this.currentView;
+      import.meta.hot.data.actionAlert = this.actionAlert;
     }
   }
 
@@ -89,6 +95,12 @@ export class WorkbenchStore {
   get boltTerminal() {
     return this.#terminalStore.boltTerminal;
   }
+  get alert() {
+    return this.actionAlert;
+  }
+  clearAlert() {
+    this.actionAlert.set(undefined);
+  }
 
   toggleTerminal(value?: boolean) {
     this.#terminalStore.toggleTerminal(value);
@@ -233,6 +245,10 @@ export class WorkbenchStore {
     // TODO: what do we wanna do and how do we wanna recover from this?
   }
 
+  setReloadedMessages(messages: string[]) {
+    this.#reloadedMessages = new Set(messages);
+  }
+
   addArtifact({ messageId, title, id, type }: ArtifactCallbackData) {
     const artifact = this.#getArtifact(messageId);
 
@@ -249,7 +265,17 @@ export class WorkbenchStore {
       title,
       closed: false,
       type,
-      runner: new ActionRunner(webcontainer, () => this.boltTerminal),
+      runner: new ActionRunner(
+        webcontainer,
+        () => this.boltTerminal,
+        (alert) => {
+          if (this.#reloadedMessages.has(messageId)) {
+            return;
+          }
+
+          this.actionAlert.set(alert);
+        },
+      ),
     });
   }
 
diff --git a/app/types/actions.ts b/app/types/actions.ts
index 08c1f39a2..6818da823 100644
--- a/app/types/actions.ts
+++ b/app/types/actions.ts
@@ -20,3 +20,10 @@ export interface StartAction extends BaseAction {
 export type BoltAction = FileAction | ShellAction | StartAction;
 
 export type BoltActionData = BoltAction | BaseAction;
+
+export interface ActionAlert {
+  type: string;
+  title: string;
+  description: string;
+  content: string;
+}
diff --git a/app/utils/shell.ts b/app/utils/shell.ts
index 0ffea4225..d079299c7 100644
--- a/app/utils/shell.ts
+++ b/app/utils/shell.ts
@@ -60,7 +60,9 @@ export class BoltShell {
   #webcontainer: WebContainer | undefined;
   #terminal: ITerminal | undefined;
   #process: WebContainerProcess | undefined;
-  executionState = atom<{ sessionId: string; active: boolean; executionPrms?: Promise<any> } | undefined>();
+  executionState = atom<
+    { sessionId: string; active: boolean; executionPrms?: Promise<any>; abort?: () => void } | undefined
+  >();
   #outputStream: ReadableStreamDefaultReader<string> | undefined;
   #shellInputStream: WritableStreamDefaultWriter<string> | undefined;
 
@@ -93,13 +95,17 @@ export class BoltShell {
     return this.#process;
   }
 
-  async executeCommand(sessionId: string, command: string): Promise<ExecutionResult> {
+  async executeCommand(sessionId: string, command: string, abort?: () => void): Promise<ExecutionResult> {
     if (!this.process || !this.terminal) {
       return undefined;
     }
 
     const state = this.executionState.get();
 
+    if (state?.active && state.abort) {
+      state.abort();
+    }
+
     /*
      * interrupt the current execution
      *  this.#shellInputStream?.write('\x03');
@@ -116,11 +122,19 @@ export class BoltShell {
 
     //wait for the execution to finish
     const executionPromise = this.getCurrentExecutionResult();
-    this.executionState.set({ sessionId, active: true, executionPrms: executionPromise });
+    this.executionState.set({ sessionId, active: true, executionPrms: executionPromise, abort });
 
     const resp = await executionPromise;
     this.executionState.set({ sessionId, active: false });
 
+    if (resp) {
+      try {
+        resp.output = cleanTerminalOutput(resp.output);
+      } catch (error) {
+        console.log('failed to format terminal output', error);
+      }
+    }
+
     return resp;
   }
 
@@ -216,6 +230,65 @@ export class BoltShell {
   }
 }
 
+/**
+ * Cleans and formats terminal output while preserving structure and paths
+ * Handles ANSI, OSC, and various terminal control sequences
+ */
+export function cleanTerminalOutput(input: string): string {
+  // Step 1: Remove OSC sequences (including those with parameters)
+  const removeOsc = input
+    .replace(/\x1b\](\d+;[^\x07\x1b]*|\d+[^\x07\x1b]*)\x07/g, '')
+    .replace(/\](\d+;[^\n]*|\d+[^\n]*)/g, '');
+
+  // Step 2: Remove ANSI escape sequences and color codes more thoroughly
+  const removeAnsi = removeOsc
+    // Remove all escape sequences with parameters
+    .replace(/\u001b\[[\?]?[0-9;]*[a-zA-Z]/g, '')
+    .replace(/\x1b\[[\?]?[0-9;]*[a-zA-Z]/g, '')
+    // Remove color codes
+    .replace(/\u001b\[[0-9;]*m/g, '')
+    .replace(/\x1b\[[0-9;]*m/g, '')
+    // Clean up any remaining escape characters
+    .replace(/\u001b/g, '')
+    .replace(/\x1b/g, '');
+
+  // Step 3: Clean up carriage returns and newlines
+  const cleanNewlines = removeAnsi
+    .replace(/\r\n/g, '\n')
+    .replace(/\r/g, '\n')
+    .replace(/\n{3,}/g, '\n\n');
+
+  // Step 4: Add newlines at key breakpoints while preserving paths
+  const formatOutput = cleanNewlines
+    // Preserve prompt line
+    .replace(/^([~\/][^\n❯]+)❯/m, '$1\n❯')
+    // Add newline before command output indicators
+    .replace(/(?<!^|\n)>/g, '\n>')
+    // Add newline before error keywords without breaking paths
+    .replace(/(?<!^|\n|\w)(error|failed|warning|Error|Failed|Warning):/g, '\n$1:')
+    // Add newline before 'at' in stack traces without breaking paths
+    .replace(/(?<!^|\n|\/)(at\s+(?!async|sync))/g, '\nat ')
+    // Ensure 'at async' stays on same line
+    .replace(/\bat\s+async/g, 'at async')
+    // Add newline before npm error indicators
+    .replace(/(?<!^|\n)(npm ERR!)/g, '\n$1');
+
+  // Step 5: Clean up whitespace while preserving intentional spacing
+  const cleanSpaces = formatOutput
+    .split('\n')
+    .map((line) => line.trim())
+    .filter((line) => line.length > 0)
+    .join('\n');
+
+  // Step 6: Final cleanup
+  return cleanSpaces
+    .replace(/\n{3,}/g, '\n\n') // Replace multiple newlines with double newlines
+    .replace(/:\s+/g, ': ') // Normalize spacing after colons
+    .replace(/\s{2,}/g, ' ') // Remove multiple spaces
+    .replace(/^\s+|\s+$/g, '') // Trim start and end
+    .replace(/\u0000/g, ''); // Remove null characters
+}
+
 export function newBoltShellProcess() {
   return new BoltShell();
 }