diff --git a/apps/rowboat/app/projects/[projectId]/copilot/app.tsx b/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
index 458a8ed1..933e723e 100644
--- a/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
+++ b/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
@@ -53,6 +53,7 @@ const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
     const [lastResponse, setLastResponse] = useState<unknown | null>(null);
     const [currentStatus, setCurrentStatus] = useState<'thinking' | 'planning' | 'generating'>('thinking');
     const statusIntervalRef = useRef<NodeJS.Timeout>();
+    const [isLastInteracted, setIsLastInteracted] = useState(isInitialState);
 
     // Notify parent of message changes
     useEffect(() => {
@@ -85,6 +86,7 @@ const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
             content: prompt
         }]);
         setResponseError(null);
+        setIsLastInteracted(true);
     }
 
     const handleApplyChange = useCallback((
@@ -313,6 +315,8 @@ const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
                         loading={loadingResponse}
                         disabled={loadingResponse}
                         initialFocus={isInitialState}
+                        shouldAutoFocus={isLastInteracted}
+                        onFocus={() => setIsLastInteracted(true)}
                     />
                 </div>
             </div>
diff --git a/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx b/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
index f58d6011..42c46dc2 100644
--- a/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
+++ b/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
@@ -50,6 +50,7 @@ export function Chat({
     const [lastAgenticRequest, setLastAgenticRequest] = useState<unknown | null>(null);
     const [lastAgenticResponse, setLastAgenticResponse] = useState<unknown | null>(null);
     const [optimisticMessages, setOptimisticMessages] = useState<z.infer<typeof apiV1.ChatMessage>[]>(chat.messages);
+    const [isLastInteracted, setIsLastInteracted] = useState(false);
 
     const getCopyContent = useCallback(() => {
         return JSON.stringify({
@@ -90,6 +91,7 @@ export function Chat({
         }];
         setMessages(updatedMessages);
         setFetchResponseError(null);
+        setIsLastInteracted(true);
     }
 
     // reset state when workflow changes
@@ -293,6 +295,8 @@ export function Chat({
                 handleUserMessage={handleUserMessage}
                 messages={messages.filter(msg => msg.content !== undefined) as any}
                 loading={loadingAssistantResponse}
+                shouldAutoFocus={isLastInteracted}
+                onFocus={() => setIsLastInteracted(true)}
             />
         </div>
     </div>;
diff --git a/apps/rowboat/components/common/compose-box-copilot.tsx b/apps/rowboat/components/common/compose-box-copilot.tsx
index 42645812..a1988416 100644
--- a/apps/rowboat/components/common/compose-box-copilot.tsx
+++ b/apps/rowboat/components/common/compose-box-copilot.tsx
@@ -20,6 +20,8 @@ interface ComposeBoxCopilotProps {
     loading: boolean;
     disabled?: boolean;
     initialFocus?: boolean;
+    shouldAutoFocus?: boolean;
+    onFocus?: () => void;
 }
 
 export function ComposeBoxCopilot({
@@ -28,18 +30,29 @@ export function ComposeBoxCopilot({
     loading,
     disabled = false,
     initialFocus = false,
+    shouldAutoFocus = false,
+    onFocus,
 }: ComposeBoxCopilotProps) {
     const [input, setInput] = useState('');
     const [isFocused, setIsFocused] = useState(false);
     const textareaRef = useRef<HTMLTextAreaElement>(null);
+    const previousMessagesLength = useRef(messages.length);
 
-    // Add effect to handle initial focus
+    // Handle initial focus
     useEffect(() => {
         if (initialFocus && textareaRef.current) {
             textareaRef.current.focus();
         }
     }, [initialFocus]);
 
+    // Handle auto-focus when new messages arrive
+    useEffect(() => {
+        if (shouldAutoFocus && messages.length > previousMessagesLength.current && textareaRef.current) {
+            textareaRef.current.focus();
+        }
+        previousMessagesLength.current = messages.length;
+    }, [messages.length, shouldAutoFocus]);
+
     function handleInput() {
         const prompt = input.trim();
         if (!prompt) {
@@ -56,6 +69,11 @@ export function ComposeBoxCopilot({
         }
     }
 
+    const handleFocus = () => {
+        setIsFocused(true);
+        onFocus?.();
+    };
+
     return (
         <div className="relative group">
             {/* Keyboard shortcut hint */}
@@ -74,7 +92,7 @@ export function ComposeBoxCopilot({
                         value={input}
                         onChange={(e) => setInput(e.target.value)}
                         onKeyDown={handleInputKeyDown}
-                        onFocus={() => setIsFocused(true)}
+                        onFocus={handleFocus}
                         onBlur={() => setIsFocused(false)}
                         disabled={disabled || loading}
                         placeholder="Type a message..."
diff --git a/apps/rowboat/components/common/compose-box-playground.tsx b/apps/rowboat/components/common/compose-box-playground.tsx
index 7547e43a..c54e875b 100644
--- a/apps/rowboat/components/common/compose-box-playground.tsx
+++ b/apps/rowboat/components/common/compose-box-playground.tsx
@@ -1,4 +1,4 @@
-import { useState, useRef } from 'react';
+import { useState, useRef, useEffect } from 'react';
 import { Textarea } from '@/components/ui/textarea';
 import { Button, Spinner } from "@heroui/react";
 
@@ -7,6 +7,8 @@ interface ComposeBoxPlaygroundProps {
     messages: any[];
     loading: boolean;
     disabled?: boolean;
+    shouldAutoFocus?: boolean;
+    onFocus?: () => void;
 }
 
 export function ComposeBoxPlayground({
@@ -14,10 +16,21 @@ export function ComposeBoxPlayground({
     messages,
     loading,
     disabled = false,
+    shouldAutoFocus = false,
+    onFocus,
 }: ComposeBoxPlaygroundProps) {
     const [input, setInput] = useState('');
     const [isFocused, setIsFocused] = useState(false);
     const textareaRef = useRef<HTMLTextAreaElement>(null);
+    const previousMessagesLength = useRef(messages.length);
+
+    // Handle auto-focus when new messages arrive
+    useEffect(() => {
+        if (shouldAutoFocus && messages.length > previousMessagesLength.current && textareaRef.current) {
+            textareaRef.current.focus();
+        }
+        previousMessagesLength.current = messages.length;
+    }, [messages.length, shouldAutoFocus]);
 
     function handleInput() {
         const prompt = input.trim();
@@ -35,6 +48,11 @@ export function ComposeBoxPlayground({
         }
     };
 
+    const handleFocus = () => {
+        setIsFocused(true);
+        onFocus?.();
+    };
+
     return (
         <div className="relative group">
             {/* Keyboard shortcut hint */}
@@ -53,7 +71,7 @@ export function ComposeBoxPlayground({
                         value={input}
                         onChange={(e) => setInput(e.target.value)}
                         onKeyDown={handleInputKeyDown}
-                        onFocus={() => setIsFocused(true)}
+                        onFocus={handleFocus}
                         onBlur={() => setIsFocused(false)}
                         disabled={disabled || loading}
                         placeholder="Type a message..."