feat: allow extra context during board onboarding

backend/app/api/board_onboarding.py

@@ -180,6 +180,10 @@ async def start_onboarding(
         "- 1 question to choose a unique name for the board lead agent (first-name style).\n"
         "- 2-4 questions to capture the user's preferences for how the board lead should work\n"
         "  (communication style, autonomy, update cadence, and output formatting).\n"
+        '- Always include a final question: "Anything else we should know?" (constraints, context,\n'
+        '  preferences). Provide an option like "Yes (I\'ll type it)" so they can fill the free-text field.\n'
+        '- If the user sends an "Additional context" message later, incorporate it and resend status=complete\n'
+        "  to update the draft (until the user confirms).\n"
         "Do NOT respond in OpenClaw chat.\n"
         "All onboarding responses MUST be sent to Mission Control via API.\n"
         f"Mission Control base URL: {base_url}\n"

backend/app/core/error_handling.py

@@ -95,7 +95,9 @@ def _error_payload(*, detail: Any, request_id: str | None) -> dict[str, Any]:
     return payload
 
 
-async def _request_validation_handler(request: Request, exc: RequestValidationError) -> JSONResponse:
+async def _request_validation_handler(
+    request: Request, exc: RequestValidationError
+) -> JSONResponse:
     # `RequestValidationError` is expected user input; don't log at ERROR.
     request_id = _get_request_id(request)
     return JSONResponse(
@@ -104,7 +106,9 @@ async def _request_validation_handler(request: Request, exc: RequestValidationEr
     )
 
 
-async def _response_validation_handler(request: Request, exc: ResponseValidationError) -> JSONResponse:
+async def _response_validation_handler(
+    request: Request, exc: ResponseValidationError
+) -> JSONResponse:
     request_id = _get_request_id(request)
     logger.exception(
         "response_validation_error",

frontend/src/components/BoardOnboardingChat.tsx

@@ -9,6 +9,7 @@ import {
 } from "@/components/ui/dialog";
 import { Button } from "@/components/ui/button";
 import { Input } from "@/components/ui/input";
+import { Textarea } from "@/components/ui/textarea";
 
 import {
   answerOnboardingApiV1BoardsBoardIdOnboardingAnswerPost,
@@ -55,7 +56,8 @@ type Question = {
 const normalizeQuestion = (value: unknown): Question | null => {
   if (!value || typeof value !== "object") return null;
   const data = value as { question?: unknown; options?: unknown };
-  if (typeof data.question !== "string" || !Array.isArray(data.options)) return null;
+  if (typeof data.question !== "string" || !Array.isArray(data.options))
+    return null;
   const options: QuestionOption[] = data.options
     .map((option, index) => {
       if (typeof option === "string") {
@@ -64,7 +66,11 @@ const normalizeQuestion = (value: unknown): Question | null => {
       if (option && typeof option === "object") {
         const raw = option as { id?: unknown; label?: unknown };
         const label =
-          typeof raw.label === "string" ? raw.label : typeof raw.id === "string" ? raw.id : null;
+          typeof raw.label === "string"
+            ? raw.label
+            : typeof raw.id === "string"
+              ? raw.id
+              : null;
         if (!label) return null;
         return {
           id: typeof raw.id === "string" ? raw.id : String(index + 1),
@@ -80,7 +86,9 @@ const normalizeQuestion = (value: unknown): Question | null => {
 
 const parseQuestion = (messages?: NormalizedMessage[] | null) => {
   if (!messages?.length) return null;
-  const lastAssistant = [...messages].reverse().find((msg) => msg.role === "assistant");
+  const lastAssistant = [...messages]
+    .reverse()
+    .find((msg) => msg.role === "assistant");
   if (!lastAssistant?.content) return null;
   try {
     return normalizeQuestion(JSON.parse(lastAssistant.content));
@@ -107,6 +115,8 @@ export function BoardOnboardingChat({
   const [session, setSession] = useState<BoardOnboardingRead | null>(null);
   const [loading, setLoading] = useState(false);
   const [otherText, setOtherText] = useState("");
+  const [extraContext, setExtraContext] = useState("");
+  const [extraContextOpen, setExtraContextOpen] = useState(false);
   const [error, setError] = useState<string | null>(null);
   const [selectedOptions, setSelectedOptions] = useState<string[]>([]);
 
@@ -114,14 +124,22 @@ export function BoardOnboardingChat({
     () => normalizeMessages(session?.messages),
     [session?.messages],
   );
-  const question = useMemo(() => parseQuestion(normalizedMessages), [normalizedMessages]);
+  const question = useMemo(
-  const draft: BoardOnboardingAgentComplete | null = session?.draft_goal ?? null;
+    () => parseQuestion(normalizedMessages),
+    [normalizedMessages],
+  );
+  const draft: BoardOnboardingAgentComplete | null =
+    session?.draft_goal ?? null;
 
   useEffect(() => {
     setSelectedOptions([]);
     setOtherText("");
   }, [question?.question]);
 
+  useEffect(() => {
+    if (draft) setExtraContextOpen(true);
+  }, [draft]);
+
   const startSession = useCallback(async () => {
     setLoading(true);
     setError(null);
@@ -133,7 +151,9 @@ export function BoardOnboardingChat({
       if (result.status !== 200) throw new Error("Unable to start onboarding.");
       setSession(result.data);
     } catch (err) {
-      setError(err instanceof Error ? err.message : "Failed to start onboarding.");
+      setError(
+        err instanceof Error ? err.message : "Failed to start onboarding.",
+      );
     } finally {
       setLoading(false);
     }
@@ -141,7 +161,8 @@ export function BoardOnboardingChat({
 
   const refreshSession = useCallback(async () => {
     try {
-      const result = await getOnboardingApiV1BoardsBoardIdOnboardingGet(boardId);
+      const result =
+        await getOnboardingApiV1BoardsBoardIdOnboardingGet(boardId);
       if (result.status !== 200) return;
       setSession(result.data);
     } catch {
@@ -160,7 +181,8 @@ export function BoardOnboardingChat({
       setLoading(true);
       setError(null);
       try {
-        const result = await answerOnboardingApiV1BoardsBoardIdOnboardingAnswerPost(
+        const result =
+          await answerOnboardingApiV1BoardsBoardIdOnboardingAnswerPost(
             boardId,
             {
               answer: value,
@@ -171,7 +193,9 @@ export function BoardOnboardingChat({
         setSession(result.data);
         setOtherText("");
       } catch (err) {
-        setError(err instanceof Error ? err.message : "Failed to submit answer.");
+        setError(
+          err instanceof Error ? err.message : "Failed to submit answer.",
+        );
       } finally {
         setLoading(false);
       }
@@ -181,10 +205,36 @@ export function BoardOnboardingChat({
 
   const toggleOption = useCallback((label: string) => {
     setSelectedOptions((prev) =>
-      prev.includes(label) ? prev.filter((item) => item !== label) : [...prev, label]
+      prev.includes(label)
+        ? prev.filter((item) => item !== label)
+        : [...prev, label],
     );
   }, []);
 
+  const submitExtraContext = useCallback(async () => {
+    const trimmed = extraContext.trim();
+    if (!trimmed) return;
+    setLoading(true);
+    setError(null);
+    try {
+      const result =
+        await answerOnboardingApiV1BoardsBoardIdOnboardingAnswerPost(boardId, {
+          answer: "Additional context",
+          other_text: trimmed,
+        });
+      if (result.status !== 200)
+        throw new Error("Unable to submit extra context.");
+      setSession(result.data);
+      setExtraContext("");
+    } catch (err) {
+      setError(
+        err instanceof Error ? err.message : "Failed to submit extra context.",
+      );
+    } finally {
+      setLoading(false);
+    }
+  }, [boardId, extraContext]);
+
   const submitAnswer = useCallback(() => {
     const trimmedOther = otherText.trim();
     if (selectedOptions.length === 0 && !trimmedOther) return;
@@ -198,7 +248,8 @@ export function BoardOnboardingChat({
     setLoading(true);
     setError(null);
     try {
-      const result = await confirmOnboardingApiV1BoardsBoardIdOnboardingConfirmPost(
+      const result =
+        await confirmOnboardingApiV1BoardsBoardIdOnboardingConfirmPost(
           boardId,
           {
             board_type: draft.board_type ?? "goal",
@@ -207,10 +258,13 @@ export function BoardOnboardingChat({
             target_date: draft.target_date ?? null,
           },
         );
-      if (result.status !== 200) throw new Error("Unable to confirm board goal.");
+      if (result.status !== 200)
+        throw new Error("Unable to confirm board goal.");
       onConfirmed(result.data);
     } catch (err) {
-      setError(err instanceof Error ? err.message : "Failed to confirm board goal.");
+      setError(
+        err instanceof Error ? err.message : "Failed to confirm board goal.",
+      );
     } finally {
       setLoading(false);
     }
@@ -246,9 +300,13 @@ export function BoardOnboardingChat({
             <p className="text-slate-700">{draft.board_type || "goal"}</p>
             {draft.user_profile ? (
               <>
-	                <p className="mt-4 font-semibold text-slate-900">User profile</p>
+                <p className="mt-4 font-semibold text-slate-900">
+                  User profile
+                </p>
                 <p className="text-slate-700">
-	                  <span className="font-medium text-slate-900">Preferred name:</span>{" "}
+                  <span className="font-medium text-slate-900">
+                    Preferred name:
+                  </span>{" "}
                   {draft.user_profile.preferred_name || "—"}
                 </p>
                 <p className="text-slate-700">
@@ -278,7 +336,8 @@ export function BoardOnboardingChat({
                   <span className="font-medium text-slate-900">
                     Communication:
                   </span>{" "}
-	                  {draft.lead_agent.identity_profile?.communication_style || "—"}
+                  {draft.lead_agent.identity_profile?.communication_style ||
+                    "—"}
                 </p>
                 <p className="text-slate-700">
                   <span className="font-medium text-slate-900">Emoji:</span>{" "}
@@ -317,6 +376,58 @@ export function BoardOnboardingChat({
               </>
             ) : null}
           </div>
+          <div className="rounded-lg border border-slate-200 bg-white p-3">
+            <div className="flex items-center justify-between gap-2">
+              <p className="text-sm font-semibold text-slate-900">
+                Extra context (optional)
+              </p>
+              <Button
+                variant="ghost"
+                size="sm"
+                type="button"
+                onClick={() => setExtraContextOpen((prev) => !prev)}
+                disabled={loading}
+              >
+                {extraContextOpen ? "Hide" : "Add"}
+              </Button>
+            </div>
+            {extraContextOpen ? (
+              <div className="mt-2 space-y-2">
+                <Textarea
+                  className="min-h-[84px]"
+                  placeholder="Anything else the agent should know before you confirm? (constraints, context, preferences, links, etc.)"
+                  value={extraContext}
+                  onChange={(event) => setExtraContext(event.target.value)}
+                  onKeyDown={(event) => {
+                    if (!(event.ctrlKey || event.metaKey)) return;
+                    if (event.key !== "Enter") return;
+                    event.preventDefault();
+                    if (loading) return;
+                    void submitExtraContext();
+                  }}
+                />
+                <div className="flex items-center justify-end">
+                  <Button
+                    variant="outline"
+                    size="sm"
+                    type="button"
+                    onClick={() => void submitExtraContext()}
+                    disabled={loading || !extraContext.trim()}
+                  >
+                    {loading ? "Sending..." : "Send context"}
+                  </Button>
+                </div>
+                <p className="text-xs text-slate-500">
+                  Tip: press Ctrl+Enter (or Cmd+Enter) to send.
+                </p>
+              </div>
+            ) : (
+              <p className="mt-2 text-xs text-slate-600">
+                Add anything that wasn&apos;t covered in the agent&apos;s
+                questions.
+              </p>
+            )}
+          </div>
           <DialogFooter>
             <Button onClick={confirmGoal} disabled={loading}>
               Confirm goal
@@ -325,7 +436,9 @@ export function BoardOnboardingChat({
         </div>
       ) : question ? (
         <div className="space-y-3">
-          <p className="text-sm font-medium text-slate-900">{question.question}</p>
+          <p className="text-sm font-medium text-slate-900">
+            {question.question}
+          </p>
           <div className="space-y-2">
             {question.options.map((option) => {
               const isSelected = selectedOptions.includes(option.label);
@@ -358,8 +471,7 @@ export function BoardOnboardingChat({
               variant="outline"
               onClick={submitAnswer}
               disabled={
-                loading ||
+                loading || (selectedOptions.length === 0 && !otherText.trim())
-                (selectedOptions.length === 0 && !otherText.trim())
               }
             >
               {loading ? "Sending..." : "Next"}
@@ -368,10 +480,64 @@ export function BoardOnboardingChat({
               <p className="text-xs text-slate-500">Sending your answer…</p>
             ) : null}
           </div>
+          <div className="rounded-lg border border-slate-200 bg-white p-3">
+            <div className="flex items-center justify-between gap-2">
+              <p className="text-sm font-semibold text-slate-900">
+                Extra context (optional)
+              </p>
+              <Button
+                variant="ghost"
+                size="sm"
+                type="button"
+                onClick={() => setExtraContextOpen((prev) => !prev)}
+                disabled={loading}
+              >
+                {extraContextOpen ? "Hide" : "Add"}
+              </Button>
+            </div>
+            {extraContextOpen ? (
+              <div className="mt-2 space-y-2">
+                <Textarea
+                  className="min-h-[84px]"
+                  placeholder="Anything else that will help the agent plan/act? (constraints, context, preferences, links, etc.)"
+                  value={extraContext}
+                  onChange={(event) => setExtraContext(event.target.value)}
+                  onKeyDown={(event) => {
+                    if (!(event.ctrlKey || event.metaKey)) return;
+                    if (event.key !== "Enter") return;
+                    event.preventDefault();
+                    if (loading) return;
+                    void submitExtraContext();
+                  }}
+                />
+                <div className="flex items-center justify-end">
+                  <Button
+                    variant="outline"
+                    size="sm"
+                    type="button"
+                    onClick={() => void submitExtraContext()}
+                    disabled={loading || !extraContext.trim()}
+                  >
+                    {loading ? "Sending..." : "Send context"}
+                  </Button>
+                </div>
+                <p className="text-xs text-slate-500">
+                  Tip: press Ctrl+Enter (or Cmd+Enter) to send.
+                </p>
+              </div>
+            ) : (
+              <p className="mt-2 text-xs text-slate-600">
+                Add anything that wasn&apos;t covered in the agent&apos;s
+                questions.
+              </p>
+            )}
+          </div>
         </div>
       ) : (
         <div className="rounded-lg border border-slate-200 bg-slate-50 p-3 text-sm text-slate-600">
-          {loading ? "Waiting for the lead agent..." : "Preparing onboarding..."}
+          {loading
+            ? "Waiting for the lead agent..."
+            : "Preparing onboarding..."}
         </div>
       )}
     </div>