diff --git a/apps/rowboat/app/projects/[projectId]/copilot/app.tsx b/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
index 251dba04..b352f8d3 100644
--- a/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
+++ b/apps/rowboat/app/projects/[projectId]/copilot/app.tsx
@@ -34,7 +34,7 @@ interface AppProps {
     dataSources?: z.infer<typeof DataSource>[];
 }
 
-const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
+const App = forwardRef<{ handleCopyChat: () => void; handleUserMessage: (message: string) => void }, AppProps>(function App({
     projectId,
     workflow,
     dispatch,
@@ -133,7 +133,8 @@ const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
     }, [messages, onCopyJson]);
 
     useImperativeHandle(ref, () => ({
-        handleCopyChat
+        handleCopyChat,
+        handleUserMessage
     }), [handleCopyChat]);
 
     return (
@@ -194,25 +195,25 @@ const App = forwardRef<{ handleCopyChat: () => void }, AppProps>(function App({
     );
 });
 
-export function Copilot({
-    projectId,
-    workflow,
-    chatContext = undefined,
-    dispatch,
-    isInitialState = false,
-    dataSources,
-}: {
+export const Copilot = forwardRef<{ handleUserMessage: (message: string) => void }, {
     projectId: string;
     workflow: z.infer<typeof Workflow>;
     chatContext?: z.infer<typeof CopilotChatContext>;
     dispatch: (action: WorkflowDispatch) => void;
     isInitialState?: boolean;
     dataSources?: z.infer<typeof DataSource>[];
-}) {
+}>(({
+    projectId,
+    workflow,
+    chatContext = undefined,
+    dispatch,
+    isInitialState = false,
+    dataSources,
+}, ref) => {
     const [copilotKey, setCopilotKey] = useState(0);
     const [showCopySuccess, setShowCopySuccess] = useState(false);
     const [messages, setMessages] = useState<z.infer<typeof CopilotMessage>[]>([]);
-    const appRef = useRef<{ handleCopyChat: () => void }>(null);
+    const appRef = useRef<{ handleCopyChat: () => void; handleUserMessage: (message: string) => void }>(null);
 
     function handleNewChat() {
         setCopilotKey(prev => prev + 1);
@@ -228,6 +229,16 @@ export function Copilot({
         }, 2000);
     }
 
+    // Expose handleUserMessage through ref
+    useImperativeHandle(ref, () => ({
+        handleUserMessage: (message: string) => {
+            const app = appRef.current as any;
+            if (app?.handleUserMessage) {
+                app.handleUserMessage(message);
+            }
+        }
+    }), []);
+
     return (
         <Panel variant="copilot"
             tourTarget="copilot"
@@ -288,5 +299,5 @@ export function Copilot({
             </div>
         </Panel>
     );
-}
+});
 
diff --git a/apps/rowboat/app/projects/[projectId]/entities/agent_config.tsx b/apps/rowboat/app/projects/[projectId]/entities/agent_config.tsx
index 1b6163f6..13425d64 100644
--- a/apps/rowboat/app/projects/[projectId]/entities/agent_config.tsx
+++ b/apps/rowboat/app/projects/[projectId]/entities/agent_config.tsx
@@ -22,6 +22,7 @@ import { EditableField } from "@/app/lib/components/editable-field";
 import { USE_TRANSFER_CONTROL_OPTIONS } from "@/app/lib/feature_flags";
 import { Input } from "@/components/ui/input";
 import { Info } from "lucide-react";
+import { useCopilot } from "../copilot/use-copilot";
 
 // Common section header styles
 const sectionHeaderStyles = "text-xs font-medium uppercase tracking-wider text-gray-500 dark:text-gray-400";
@@ -44,6 +45,7 @@ export function AgentConfig({
     handleUpdate,
     handleClose,
     useRag,
+    triggerCopilotChat,
 }: {
     projectId: string,
     workflow: z.infer<typeof Workflow>,
@@ -56,6 +58,7 @@ export function AgentConfig({
     handleUpdate: (agent: z.infer<typeof WorkflowAgent>) => void,
     handleClose: () => void,
     useRag: boolean,
+    triggerCopilotChat: (message: string) => void,
 }) {
     const [isAdvancedConfigOpen, setIsAdvancedConfigOpen] = useState(false);
     const [showGenerateModal, setShowGenerateModal] = useState(false);
@@ -65,11 +68,42 @@ export function AgentConfig({
     const [localName, setLocalName] = useState(agent.name);
     const [nameError, setNameError] = useState<string | null>(null);
     const [activeTab, setActiveTab] = useState<TabType>('instructions');
+    const [showRagCta, setShowRagCta] = useState(false);
+    const [previousRagSources, setPreviousRagSources] = useState<string[]>([]);
     
+    const {
+        start: startCopilotChat,
+    } = useCopilot({
+        projectId,
+        workflow,
+        context: null,
+        dataSources
+    });
+
     useEffect(() => {
         setLocalName(agent.name);
     }, [agent.name]);
 
+    // Track changes in RAG datasources
+    useEffect(() => {
+        const currentSources = agent.ragDataSources || [];
+        // Show CTA when transitioning from 0 to 1 datasource
+        if (currentSources.length === 1 && previousRagSources.length === 0) {
+            setShowRagCta(true);
+        }
+        // Hide CTA when all datasources are deleted
+        if (currentSources.length === 0) {
+            setShowRagCta(false);
+        }
+        setPreviousRagSources(currentSources);
+    }, [agent.ragDataSources]);
+
+    const handleUpdateInstructions = async () => {
+        const message = `Update the instructions for agent "${agent.name}" to use the rag tool (rag_search) since data sources have been added. If this has already been done, do not take any action, but let me know.`;
+        triggerCopilotChat(message);
+        setShowRagCta(false);
+    };
+
     // Add effect to handle control type update when transfer control is disabled
     useEffect(() => {
         if (!USE_TRANSFER_CONTROL_OPTIONS && agent.controlType !== 'retain') {
@@ -455,7 +489,7 @@ export function AgentConfig({
                                         RAG
                                     </label>
                                     <div className="flex flex-col gap-3">
-                                        <div>
+                                        <div className="flex items-center gap-3">
                                             <Select
                                                 variant="bordered"
                                                 placeholder="Add data source"
@@ -481,6 +515,17 @@ export function AgentConfig({
                                                     ))
                                                 }
                                             </Select>
+
+                                            {showRagCta && (
+                                                <CustomButton
+                                                    variant="primary"
+                                                    size="sm"
+                                                    onClick={handleUpdateInstructions}
+                                                    className="whitespace-nowrap"
+                                                >
+                                                    Update Instructions
+                                                </CustomButton>
+                                            )}
                                         </div>
 
                                         <div className="flex flex-col gap-2">
diff --git a/apps/rowboat/app/projects/[projectId]/workflow/workflow_editor.tsx b/apps/rowboat/app/projects/[projectId]/workflow/workflow_editor.tsx
index a3e79aad..4db035b1 100644
--- a/apps/rowboat/app/projects/[projectId]/workflow/workflow_editor.tsx
+++ b/apps/rowboat/app/projects/[projectId]/workflow/workflow_editor.tsx
@@ -611,6 +611,16 @@ export function WorkflowEditor({
     const [isMcpImportModalOpen, setIsMcpImportModalOpen] = useState(false);
     const [isInitialState, setIsInitialState] = useState(true);
     const [showTour, setShowTour] = useState(true);
+    const copilotRef = useRef<{ handleUserMessage: (message: string) => void }>(null);
+
+    // Function to trigger copilot chat
+    const triggerCopilotChat = useCallback((message: string) => {
+        setShowCopilot(true);
+        // Small delay to ensure copilot is mounted
+        setTimeout(() => {
+            copilotRef.current?.handleUserMessage(message);
+        }, 100);
+    }, []);
 
     console.log(`workflow editor chat key: ${state.present.chatKey}`);
 
@@ -992,6 +1002,7 @@ export function WorkflowEditor({
                     handleUpdate={handleUpdateAgent.bind(null, state.present.selection.name)}
                     handleClose={handleUnselectAgent}
                     useRag={useRag}
+                    triggerCopilotChat={triggerCopilotChat}
                 />}
                 {state.present.selection?.type === "tool" && <ToolConfig
                     key={state.present.selection.name}
@@ -1020,6 +1031,7 @@ export function WorkflowEditor({
                         onResize={(size) => setCopilotWidth(size)}
                     >
                         <Copilot
+                            ref={copilotRef}
                             projectId={state.present.workflow.projectId}
                             workflow={state.present.workflow}
                             dispatch={dispatch}