diff --git a/ui/desktop/src/App.tsx b/ui/desktop/src/App.tsx
index 19a683dfe195..edac767f575c 100644
--- a/ui/desktop/src/App.tsx
+++ b/ui/desktop/src/App.tsx
@@ -359,6 +359,7 @@ export default function App() {
   const [extensionConfirmTitle, setExtensionConfirmTitle] = useState<string>('');
   const [isLoadingSession, setIsLoadingSession] = useState(false);
   const [isGoosehintsModalOpen, setIsGoosehintsModalOpen] = useState(false);
+  const [agentWaitingMessage, setAgentWaitingMessage] = useState<string | null>(null);
 
   // Add separate state for pair chat to maintain its own conversation
   const [pairChat, setPairChat] = useState<ChatType>({
@@ -449,16 +450,19 @@ export default function App() {
         getExtensions,
         addExtension,
         setPairChat,
+        setMessage: setAgentWaitingMessage,
         provider: provider as string,
         model: model as string,
       });
     };
 
-    initialize().catch((error) => {
-      console.error('Fatal error during initialization:', error);
-      setFatalError(error instanceof Error ? error.message : 'Unknown error occurred');
-    });
-  }, [getExtensions, addExtension, read, setPairChat]);
+    initialize()
+      .then(() => setAgentWaitingMessage(null))
+      .catch((error) => {
+        console.error('Fatal error during initialization:', error);
+        setFatalError(error instanceof Error ? error.message : 'Unknown error occurred');
+      });
+  }, [getExtensions, addExtension, read, setPairChat, setAgentWaitingMessage]);
 
   useEffect(() => {
     console.log('Sending reactReady signal to Electron');
@@ -838,7 +842,12 @@ export default function App() {
               <Route
                 path="/"
                 element={
-                  <ChatProvider chat={chat} setChat={setChat} contextKey="hub">
+                  <ChatProvider
+                    chat={chat}
+                    setChat={setChat}
+                    contextKey="hub"
+                    agentWaitingMessage={agentWaitingMessage}
+                  >
                     <AppLayout setIsGoosehintsModalOpen={setIsGoosehintsModalOpen} />
                   </ChatProvider>
                 }
@@ -864,6 +873,7 @@ export default function App() {
                         chat={pairChat}
                         setChat={setPairChat}
                         contextKey={`pair-${pairChat.id}`}
+                        agentWaitingMessage={agentWaitingMessage}
                         key={pairChat.id}
                       >
                         <PairRouteWrapper
diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index cea578b0386f..7fc60a87915f 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -136,6 +136,7 @@ export default function ChatInput({
   // Draft functionality - get chat context and global draft context
   // We need to handle the case where ChatInput is used without ChatProvider (e.g., in Hub)
   const chatContext = useChatContext(); // This should always be available now
+  const agentIsReady = chatContext === null || chatContext.agentWaitingMessage === null;
   const draftLoadedRef = useRef(false);
 
   // Debug logging for draft context
@@ -1060,6 +1061,7 @@ export default function ChatInput({
       const canSubmit =
         !isLoading &&
         !isLoadingCompaction &&
+        agentIsReady &&
         (displayValue.trim() ||
           pastedImages.some((img) => img.filePath && !img.error && !img.isLoading) ||
           allDroppedFiles.some((file) => !file.error && !file.isLoading));
@@ -1074,6 +1076,7 @@ export default function ChatInput({
     const canSubmit =
       !isLoading &&
       !isLoadingCompaction &&
+      agentIsReady &&
       (displayValue.trim() ||
         pastedImages.some((img) => img.filePath && !img.error && !img.isLoading) ||
         allDroppedFiles.some((file) => !file.error && !file.isLoading));
@@ -1337,46 +1340,56 @@ export default function ChatInput({
               <Stop />
             </Button>
           ) : (
-            <Button
-              type="submit"
-              size="sm"
-              shape="round"
-              variant="outline"
-              disabled={
-                !hasSubmittableContent ||
-                isAnyImageLoading ||
-                isAnyDroppedFileLoading ||
-                isRecording ||
-                isTranscribing ||
-                isLoadingCompaction
-              }
-              className={`rounded-full px-10 py-2 flex items-center gap-2 ${
-                !hasSubmittableContent ||
-                isAnyImageLoading ||
-                isAnyDroppedFileLoading ||
-                isRecording ||
-                isTranscribing ||
-                isLoadingCompaction
-                  ? 'bg-slate-600 text-white cursor-not-allowed opacity-50 border-slate-600'
-                  : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600 hover:cursor-pointer'
-              }`}
-              title={
-                isLoadingCompaction
-                  ? 'Summarizing conversation...'
-                  : isAnyImageLoading
-                    ? 'Waiting for images to save...'
-                    : isAnyDroppedFileLoading
-                      ? 'Processing dropped files...'
-                      : isRecording
-                        ? 'Recording...'
-                        : isTranscribing
-                          ? 'Transcribing...'
-                          : 'Send'
-              }
-            >
-              <Send className="w-4 h-4" />
-              <span className="text-sm">Send</span>
-            </Button>
+            <Tooltip>
+              <TooltipTrigger asChild>
+                <span>
+                  <Button
+                    type="submit"
+                    size="sm"
+                    shape="round"
+                    variant="outline"
+                    disabled={
+                      !hasSubmittableContent ||
+                      isAnyImageLoading ||
+                      isAnyDroppedFileLoading ||
+                      isRecording ||
+                      isTranscribing ||
+                      isLoadingCompaction ||
+                      !agentIsReady
+                    }
+                    className={`rounded-full px-10 py-2 flex items-center gap-2 ${
+                      !hasSubmittableContent ||
+                      isAnyImageLoading ||
+                      isAnyDroppedFileLoading ||
+                      isRecording ||
+                      isTranscribing ||
+                      isLoadingCompaction ||
+                      !agentIsReady
+                        ? 'bg-slate-600 text-white cursor-not-allowed opacity-50 border-slate-600'
+                        : 'bg-slate-600 text-white hover:bg-slate-700 border-slate-600 hover:cursor-pointer'
+                    }`}
+                  >
+                    <Send className="w-4 h-4" />
+                    <span className="text-sm">Send</span>
+                  </Button>
+                </span>
+              </TooltipTrigger>
+              <TooltipContent>
+                <p>
+                  {isLoadingCompaction
+                    ? 'Summarizing conversation...'
+                    : isAnyImageLoading
+                      ? 'Waiting for images to save...'
+                      : isAnyDroppedFileLoading
+                        ? 'Processing dropped files...'
+                        : isRecording
+                          ? 'Recording...'
+                          : isTranscribing
+                            ? 'Transcribing...'
+                            : (chatContext?.agentWaitingMessage ?? 'Send')}
+                </p>
+              </TooltipContent>
+            </Tooltip>
           )}
 
           {/* Recording/transcribing status indicator - positioned above the button row */}
diff --git a/ui/desktop/src/components/InterruptionHandler.tsx b/ui/desktop/src/components/InterruptionHandler.tsx
index b6e3d1f45366..2fd57df1265a 100644
--- a/ui/desktop/src/components/InterruptionHandler.tsx
+++ b/ui/desktop/src/components/InterruptionHandler.tsx
@@ -60,28 +60,28 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
           bg: 'bg-red-50 dark:bg-red-950/20',
           border: 'border-red-200 dark:border-red-800/50',
           text: 'text-red-800 dark:text-red-200',
-          accent: 'text-red-600 dark:text-red-400'
+          accent: 'text-red-600 dark:text-red-400',
         };
       case 'pause':
         return {
           bg: 'bg-amber-50 dark:bg-amber-950/20',
           border: 'border-amber-200 dark:border-amber-800/50',
           text: 'text-amber-800 dark:text-amber-200',
-          accent: 'text-amber-600 dark:text-amber-400'
+          accent: 'text-amber-600 dark:text-amber-400',
         };
       case 'redirect':
         return {
           bg: 'bg-blue-50 dark:bg-blue-950/20',
           border: 'border-blue-200 dark:border-blue-800/50',
           text: 'text-blue-800 dark:text-blue-200',
-          accent: 'text-blue-600 dark:text-blue-400'
+          accent: 'text-blue-600 dark:text-blue-400',
         };
       default:
         return {
           bg: 'bg-orange-50 dark:bg-orange-950/20',
           border: 'border-orange-200 dark:border-orange-800/50',
           text: 'text-orange-800 dark:text-orange-200',
-          accent: 'text-orange-600 dark:text-orange-400'
+          accent: 'text-orange-600 dark:text-orange-400',
         };
     }
   };
@@ -98,33 +98,43 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
 
   const getActionTitle = () => {
     switch (match.keyword.action) {
-      case 'stop': return 'Stop Processing';
-      case 'pause': return 'Pause Processing';
-      case 'redirect': return 'Redirect Processing';
-      default: return 'Interrupt Processing';
+      case 'stop':
+        return 'Stop Processing';
+      case 'pause':
+        return 'Pause Processing';
+      case 'redirect':
+        return 'Redirect Processing';
+      default:
+        return 'Interrupt Processing';
     }
   };
 
   const getActionDescription = () => {
     switch (match.keyword.action) {
-      case 'stop': 
+      case 'stop':
         return 'This will immediately stop the current processing and clear any queued messages.';
-      case 'pause': 
+      case 'pause':
         return 'This will pause the current processing. Queued messages will be preserved.';
-      case 'redirect': 
+      case 'redirect':
         return 'This will stop current processing and redirect to a new task.';
-      default: 
+      default:
         return 'This will interrupt the current processing.';
     }
   };
 
   return (
-    <div className={`fixed inset-0 bg-black/50 backdrop-blur-sm flex items-center justify-center z-50 p-4 ${className}`}>
-      <div className={`w-full max-w-md mx-auto transition-all duration-300 ease-out ${
-        isVisible ? 'scale-100 opacity-100' : 'scale-95 opacity-0'
-      }`}>
+    <div
+      className={`fixed inset-0 bg-black/50 backdrop-blur-sm flex items-center justify-center z-50 p-4 ${className}`}
+    >
+      <div
+        className={`w-full max-w-md mx-auto transition-all duration-300 ease-out ${
+          isVisible ? 'scale-100 opacity-100' : 'scale-95 opacity-0'
+        }`}
+      >
         {/* Main card */}
-        <div className={`rounded-xl border shadow-2xl backdrop-blur-xl ${colors.bg} ${colors.border}`}>
+        <div
+          className={`rounded-xl border shadow-2xl backdrop-blur-xl ${colors.bg} ${colors.border}`}
+        >
           {/* Header */}
           <div className="p-6 border-b border-current/10">
             <div className="flex items-start gap-4">
@@ -132,14 +142,12 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
                 {getIcon()}
               </div>
               <div className="flex-1">
-                <h3 className={`text-lg font-semibold ${colors.text}`}>
-                  {getActionTitle()}
-                </h3>
-                <p className={`text-sm mt-1 ${colors.accent}`}>
-                  Detected: "{match.matchedText}"
-                </p>
+                <h3 className={`text-lg font-semibold ${colors.text}`}>{getActionTitle()}</h3>
+                <p className={`text-sm mt-1 ${colors.accent}`}>Detected: "{match.matchedText}"</p>
               </div>
-              <div className={`text-xs px-2 py-1 rounded-full bg-white/30 dark:bg-black/20 ${colors.text}`}>
+              <div
+                className={`text-xs px-2 py-1 rounded-full bg-white/30 dark:bg-black/20 ${colors.text}`}
+              >
                 {Math.round(match.confidence * 100)}% confident
               </div>
             </div>
@@ -149,9 +157,7 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
           <div className="p-6">
             <div className="flex items-start gap-3 mb-4">
               <AlertCircle className={`w-4 h-4 mt-0.5 flex-shrink-0 ${colors.accent}`} />
-              <p className={`text-sm leading-relaxed ${colors.text}`}>
-                {getActionDescription()}
-              </p>
+              <p className={`text-sm leading-relaxed ${colors.text}`}>{getActionDescription()}</p>
             </div>
 
             {/* Redirect input */}
@@ -178,10 +184,13 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
                 <span className={colors.text}>{Math.round(match.confidence * 100)}%</span>
               </div>
               <div className="w-full bg-white/30 dark:bg-black/20 rounded-full h-2">
-                <div 
+                <div
                   className={`h-2 rounded-full transition-all duration-500 ${
-                    match.confidence > 0.8 ? 'bg-green-500' : 
-                    match.confidence > 0.6 ? 'bg-amber-500' : 'bg-red-500'
+                    match.confidence > 0.8
+                      ? 'bg-green-500'
+                      : match.confidence > 0.6
+                        ? 'bg-amber-500'
+                        : 'bg-red-500'
                   }`}
                   style={{ width: `${match.confidence * 100}%` }}
                 />
@@ -204,7 +213,11 @@ export const InterruptionHandler: React.FC<InterruptionHandlerProps> = ({
               className={`flex-1 bg-white/80 hover:bg-white dark:bg-white/10 dark:hover:bg-white/20 ${colors.text} font-medium shadow-md hover:shadow-lg transition-all duration-200`}
             >
               <Zap className="w-4 h-4 mr-2" />
-              {showRedirectInput ? 'Redirect' : match.keyword.action === 'stop' ? 'Stop' : 'Confirm'}
+              {showRedirectInput
+                ? 'Redirect'
+                : match.keyword.action === 'stop'
+                  ? 'Stop'
+                  : 'Confirm'}
             </Button>
           </div>
         </div>
diff --git a/ui/desktop/src/components/ui/Pill.tsx b/ui/desktop/src/components/ui/Pill.tsx
index 7969d6555a46..ce4cc0ef60b3 100644
--- a/ui/desktop/src/components/ui/Pill.tsx
+++ b/ui/desktop/src/components/ui/Pill.tsx
@@ -22,11 +22,13 @@ export function Pill({
   disabled = false,
   animated = false,
 }: PillProps) {
-  const baseStyles = 'inline-flex items-center justify-center rounded-full transition-all duration-300 ease-out font-medium';
-  
+  const baseStyles =
+    'inline-flex items-center justify-center rounded-full transition-all duration-300 ease-out font-medium';
+
   const variants = {
     default: 'bg-background border border-border hover:bg-muted/50',
-    glass: 'bg-white/10 dark:bg-black/10 backdrop-blur-xl border border-white/20 dark:border-white/10 shadow-lg shadow-black/5 dark:shadow-black/20 hover:bg-white/15 dark:hover:bg-black/15 hover:shadow-xl',
+    glass:
+      'bg-white/10 dark:bg-black/10 backdrop-blur-xl border border-white/20 dark:border-white/10 shadow-lg shadow-black/5 dark:shadow-black/20 hover:bg-white/15 dark:hover:bg-black/15 hover:shadow-xl',
     solid: 'bg-background border border-border shadow-md hover:shadow-lg hover:scale-105',
     gradient: 'bg-gradient-to-r shadow-lg hover:shadow-xl hover:scale-105 border-0',
     glow: 'shadow-lg hover:shadow-xl hover:scale-105 border-0',
@@ -54,9 +56,11 @@ export function Pill({
       glass: 'text-red-700 dark:text-red-300 hover:text-red-800 dark:hover:text-red-200',
     },
     purple: {
-      gradient: 'from-purple-500 to-purple-600 hover:from-purple-600 hover:to-purple-700 text-white',
+      gradient:
+        'from-purple-500 to-purple-600 hover:from-purple-600 hover:to-purple-700 text-white',
       glow: 'bg-purple-500 hover:bg-purple-600 text-white shadow-purple-500/25 hover:shadow-purple-500/40',
-      glass: 'text-purple-700 dark:text-purple-300 hover:text-purple-800 dark:hover:text-purple-200',
+      glass:
+        'text-purple-700 dark:text-purple-300 hover:text-purple-800 dark:hover:text-purple-200',
     },
     slate: {
       gradient: 'from-slate-500 to-slate-600 hover:from-slate-600 hover:to-slate-700 text-white',
@@ -73,20 +77,21 @@ export function Pill({
   };
 
   const animatedStyles = animated ? 'animate-pulse' : '';
-  
-  const disabledStyles = disabled 
-    ? 'opacity-50 cursor-not-allowed pointer-events-none' 
-    : onClick 
-      ? 'cursor-pointer hover:scale-105 active:scale-95' 
+
+  const disabledStyles = disabled
+    ? 'opacity-50 cursor-not-allowed pointer-events-none'
+    : onClick
+      ? 'cursor-pointer hover:scale-105 active:scale-95'
       : '';
 
-  const colorStyles = variant === 'gradient' 
-    ? colors[color].gradient 
-    : variant === 'glow' 
-      ? colors[color].glow
-      : variant === 'glass'
-        ? colors[color].glass
-        : '';
+  const colorStyles =
+    variant === 'gradient'
+      ? colors[color].gradient
+      : variant === 'glow'
+        ? colors[color].glow
+        : variant === 'glass'
+          ? colors[color].glass
+          : '';
 
   return (
     <div
diff --git a/ui/desktop/src/contexts/ChatContext.tsx b/ui/desktop/src/contexts/ChatContext.tsx
index 8ae5ccd47d72..e9f1daabff71 100644
--- a/ui/desktop/src/contexts/ChatContext.tsx
+++ b/ui/desktop/src/contexts/ChatContext.tsx
@@ -21,6 +21,7 @@ interface ChatContextType {
   clearDraft: () => void;
   // Context identification
   contextKey: string; // 'hub' or 'pair-{sessionId}'
+  agentWaitingMessage: string | null;
 }
 
 const ChatContext = createContext<ChatContextType | undefined>(undefined);
@@ -30,12 +31,14 @@ interface ChatProviderProps {
   chat: ChatType;
   setChat: (chat: ChatType) => void;
   contextKey?: string; // Optional context key, defaults to 'hub'
+  agentWaitingMessage: string | null;
 }
 
 export const ChatProvider: React.FC<ChatProviderProps> = ({
   children,
   chat,
   setChat,
+  agentWaitingMessage,
   contextKey = 'hub',
 }) => {
   const draftContext = useDraftContext();
@@ -108,6 +111,7 @@ export const ChatProvider: React.FC<ChatProviderProps> = ({
     setDraft,
     clearDraft,
     contextKey,
+    agentWaitingMessage,
   };
 
   return <ChatContext.Provider value={value}>{children}</ChatContext.Provider>;
diff --git a/ui/desktop/src/utils/appInitialization.ts b/ui/desktop/src/utils/appInitialization.ts
index d0fcd797c5ae..d45674b39105 100644
--- a/ui/desktop/src/utils/appInitialization.ts
+++ b/ui/desktop/src/utils/appInitialization.ts
@@ -14,6 +14,7 @@ interface InitializationDependencies {
   getExtensions?: (b: boolean) => Promise<FixedExtensionEntry[]>;
   addExtension?: (name: string, config: ExtensionConfig, enabled: boolean) => Promise<void>;
   setPairChat: (chat: ChatType | ((prev: ChatType) => ChatType)) => void;
+  setMessage: (message: string | null) => void;
   provider: string;
   model: string;
 }
@@ -22,6 +23,7 @@ export const initializeApp = async ({
   getExtensions,
   addExtension,
   setPairChat,
+  setMessage,
   provider,
   model,
 }: InitializationDependencies) => {
@@ -87,6 +89,7 @@ export const initializeApp = async ({
         initPromises.push(costDbPromise);
       }
 
+      setMessage('starting extensions...');
       await Promise.all(initPromises);
     } catch (error) {
       console.error('Error in system initialization:', error);
diff --git a/ui/desktop/src/utils/interruptionDetector.ts b/ui/desktop/src/utils/interruptionDetector.ts
index a441cdf6a812..74eb108981ca 100644
--- a/ui/desktop/src/utils/interruptionDetector.ts
+++ b/ui/desktop/src/utils/interruptionDetector.ts
@@ -15,32 +15,32 @@ export const INTERRUPTION_KEYWORDS: InterruptionKeyword[] = [
     keyword: 'stop',
     variations: ['stop', 'halt', 'cease', 'quit', 'end', 'abort', 'cancel'],
     priority: 'high',
-    action: 'stop'
+    action: 'stop',
   },
   {
     keyword: 'wait',
     variations: ['wait', 'hold', 'pause', 'hold on', 'wait up', 'hold up'],
-    priority: 'high', 
-    action: 'pause'
+    priority: 'high',
+    action: 'pause',
   },
   {
     keyword: 'no',
     variations: ['no', 'nope', 'nah', 'wrong', 'incorrect', 'not right'],
     priority: 'medium',
-    action: 'stop'
+    action: 'stop',
   },
   {
     keyword: 'actually',
     variations: ['actually', 'instead', 'rather', 'better idea', 'change of plans'],
     priority: 'medium',
-    action: 'redirect'
+    action: 'redirect',
   },
   {
     keyword: 'nevermind',
     variations: ['nevermind', 'never mind', 'forget it', 'ignore that', 'disregard'],
     priority: 'medium',
-    action: 'stop'
-  }
+    action: 'stop',
+  },
 ];
 
 export interface InterruptionMatch {
@@ -59,7 +59,7 @@ export function detectInterruption(input: string): InterruptionMatch | null {
   }
 
   const normalizedInput = input.toLowerCase().trim();
-  
+
   // Check for exact matches first (highest confidence)
   for (const keyword of INTERRUPTION_KEYWORDS) {
     for (const variation of keyword.variations) {
@@ -68,7 +68,7 @@ export function detectInterruption(input: string): InterruptionMatch | null {
           keyword,
           matchedText: variation,
           confidence: 1.0,
-          shouldInterrupt: true
+          shouldInterrupt: true,
         };
       }
     }
@@ -77,12 +77,15 @@ export function detectInterruption(input: string): InterruptionMatch | null {
   // Check for matches at the beginning of input (high confidence)
   for (const keyword of INTERRUPTION_KEYWORDS) {
     for (const variation of keyword.variations) {
-      if (normalizedInput.startsWith(variation + ' ') || normalizedInput.startsWith(variation + ',')) {
+      if (
+        normalizedInput.startsWith(variation + ' ') ||
+        normalizedInput.startsWith(variation + ',')
+      ) {
         return {
           keyword,
           matchedText: variation,
           confidence: 0.9,
-          shouldInterrupt: true
+          shouldInterrupt: true,
         };
       }
     }
@@ -97,7 +100,7 @@ export function detectInterruption(input: string): InterruptionMatch | null {
             keyword,
             matchedText: variation,
             confidence: 0.7,
-            shouldInterrupt: keyword.priority === 'high'
+            shouldInterrupt: keyword.priority === 'high',
           };
         }
       }