fix(seer): Add timeout recovery for Explorer chat

static/app/views/seerExplorer/components/inputSection.tsx

@@ -46,7 +46,6 @@ interface InputSectionProps {
   canSendMessage?: boolean;
   fileApprovalActions?: FileApprovalActions;
   interruptState?: 'can-interrupt' | 'requested' | 'completed' | 'disabled';
-  isTimedOut?: boolean;
   questionActions?: QuestionActions;
 }
 
@@ -56,7 +55,6 @@ export function InputSection({
   inputValue,
   canSendMessage = true,
   interruptState = 'disabled',
-  isTimedOut = false,
   onCreatePR,
   onInputChange,
   onInputClick,
@@ -257,21 +255,17 @@ export function InputSection({
   return (
     <InputBlock>
       <InputRow>
-        <StyledInputGroup
-          isWarningPlaceholder={interruptState === 'completed' || isTimedOut}
-        >
+        <StyledInputGroup isWarningPlaceholder={interruptState === 'completed'}>
           <InputGroup.TextArea
             ref={textAreaRef}
             value={inputValue}
             onChange={onInputChange}
             onKeyDown={onKeyDown}
             onClick={onInputClick}
             placeholder={
-              isTimedOut
-                ? t('Response timed out. Please try again.')
-                : interruptState === 'completed'
-                  ? t('Interrupted. What should Seer do instead?')
-                  : t('Ask Seer a question, or press / for commands.')
+              interruptState === 'completed'
+                ? t('Interrupted. What should Seer do instead?')
+                : t('Ask Seer a question, or press / for commands.')
             }
             rows={1}
             maxRows={5}

static/app/views/seerExplorer/components/seerExplorerContent.spec.tsx

@@ -574,6 +574,66 @@ describe('SeerExplorerContent', () => {
     });
   });
 
+  describe('Timeout Recovery', () => {
+    it('shows the warning and retries the latest user turn', async () => {
+      const sendMessage = jest.fn();
+      const startNewSession = jest.fn();
+      jest.spyOn(useSeerExplorerModule, 'useSeerExplorer').mockReturnValue({
+        ...defaultHookReturn,
+        isTimedOut: true,
+        runId: 123,
+        sendMessage,
+        startNewSession,
+        sessionData: {
+          blocks: [
+            {
+              id: 'user-1',
+              message: {role: 'user', content: 'First question'},
+              timestamp: '2024-01-01T00:00:00Z',
+            },
+            {
+              id: 'assistant-1',
+              message: {role: 'assistant', content: 'First answer'},
+              timestamp: '2024-01-01T00:01:00Z',
+            },
+            {
+              id: 'user-2',
+              message: {role: 'user', content: 'Timed out question'},
+              timestamp: '2024-01-01T00:02:00Z',
+            },
+          ],
+          status: 'error',
+          updated_at: '2024-01-01T00:03:00Z',
+          failure_reason: 'timeout',
+        },
+      });
+
+      render(
+        <PictureInPictureProvider>
+          <SeerExplorerSessionsProvider>
+            <SeerExplorerContent
+              getPageReferrer={mockGetPageReferrer}
+              onClose={() => {}}
+            />
+          </SeerExplorerSessionsProvider>
+        </PictureInPictureProvider>,
+        {organization}
+      );
+
+      expect(await screen.findByText('Response timed out.')).toBeInTheDocument();
+      expect(screen.getByTestId('seer-explorer-input')).toHaveAttribute(
+        'placeholder',
+        'Ask Seer a question, or press / for commands.'
+      );
+
+      await userEvent.click(screen.getByRole('button', {name: 'Retry'}));
+      expect(sendMessage).toHaveBeenCalledWith('Timed out question', 2);
+
+      await userEvent.click(screen.getByRole('button', {name: 'New chat'}));
+      expect(startNewSession).toHaveBeenCalledTimes(1);
+    });
+  });
+
   describe('Input Persistence', () => {
     it('restores the persisted draft when the drawer remounts', async () => {
       jest.spyOn(useSeerExplorerModule, 'useSeerExplorer').mockReturnValue({

static/app/views/seerExplorer/components/seerExplorerContent.tsx

@@ -2,17 +2,19 @@ import {Fragment, useCallback, useEffect, useMemo, useRef, type ReactNode} from
 import styled from '@emotion/styled';
 import {skipToken, useQuery} from '@tanstack/react-query';
 
+import {Alert} from '@sentry/scraps/alert';
 import {Button} from '@sentry/scraps/button';
-import {Flex, Stack} from '@sentry/scraps/layout';
+import {Container, Flex, Stack} from '@sentry/scraps/layout';
 import {usePictureInPicture} from '@sentry/scraps/pictureInPicture';
+import {Text} from '@sentry/scraps/text';
 
 import {addErrorMessage, addSuccessMessage} from 'sentry/actionCreators/indicator';
 import {
   AutofixChatProvider,
   type SendMessageOptions,
 } from 'sentry/components/seer/autofixChatContext';
 import {SEER_AGENTS_PROJECT_ID} from 'sentry/constants';
-import {IconClose} from 'sentry/icons';
+import {IconClose, IconRefresh} from 'sentry/icons';
 import {t} from 'sentry/locale';
 import type {OrganizationIntegration} from 'sentry/types/integrations';
 import {trackAnalytics} from 'sentry/utils/analytics';
@@ -225,6 +227,15 @@ export function SeerExplorerContent({
     sessionData.owner_user_id.toString() !== user.id;
 
   const blocks = useMemo(() => sessionData?.blocks || [], [sessionData?.blocks]);
+  const retryTarget = useMemo(() => {
+    for (let index = blocks.length - 1; index >= 0; index--) {
+      const block = blocks[index];
+      if (block?.message.role === 'user' && block.message.content?.trim()) {
+        return {insertIndex: index, query: block.message.content};
+      }
+    }
+    return null;
+  }, [blocks]);
   const isAwaitingUserInput = sessionData?.status === 'awaiting_user_input';
   const pendingInput = sessionData?.pending_user_input ?? null;
   const isAgentWriteApprovalPending =
@@ -465,6 +476,14 @@ export function SeerExplorerContent({
     closeMenu();
   };
 
+  const handleRetry = useCallback(() => {
+    if (!retryTarget || readOnly) {
+      return;
+    }
+    sendMessage(retryTarget.query, retryTarget.insertIndex);
+    userScrolledUpRef.current = false;
+  }, [readOnly, retryTarget, sendMessage]);
+
   // - Scroll effects ---------------------------------------------------------
 
   useEffect(() => {
@@ -680,13 +699,33 @@ export function SeerExplorerContent({
             </Fragment>
           )}
         </BlocksContainer>
+        {isTimedOut && (
+          <Container padding="0 xl">
+            <Alert
+              variant="warning"
+              trailingItems={
+                retryTarget &&
+                !readOnly && (
+                  <Alert.Button
+                    variant="secondary"
+                    icon={<IconRefresh />}
+                    onClick={handleRetry}
+                  >
+                    {t('Retry')}
+                  </Alert.Button>
+                )
+              }
+            >
+              <Text>{t('Response timed out.')}</Text>
+            </Alert>
+          </Container>
+        )}
         <InputSection
           blocks={blocks}
           enabled={!readOnly}
           inputValue={inputValue}
           canSendMessage={canSendMessage}
           interruptState={interruptState}
-          isTimedOut={isTimedOut}
           onCreatePR={createPR}
           onInputChange={handleInputChange}
           onInputClick={handleInputClick}

static/app/views/seerExplorer/hooks/useSeerExplorer.tsx

@@ -217,6 +217,7 @@ export const useSeerExplorer = () => {
                 ...prev,
                 session: {
                   ...prev.session,
+                  failure_reason: null,
                   status: 'processing',
                   updated_at: new Date().toISOString(),
                 },
@@ -296,6 +297,7 @@ export const useSeerExplorer = () => {
                   ...prev,
                   session: {
                     ...prev.session,
+                    failure_reason: null,
                     status: 'processing',
                     updated_at: new Date().toISOString(),
                   },
@@ -358,6 +360,7 @@ export const useSeerExplorer = () => {
                   ...prev,
                   session: {
                     ...prev.session,
+                    failure_reason: null,
                     status: 'processing',
                     updated_at: new Date().toISOString(),
                   },

static/app/views/seerExplorer/hooks/useSeerExplorerPolling.spec.tsx

@@ -48,4 +48,34 @@ describe('useSeerExplorerPolling', () => {
     expect(result.current.isPolling).toBe(false);
     expect(result.current.errorStatusCode).toBe(404);
   });
+
+  it.each([
+    ['timeout', 'timed-out', true],
+    ['stalled', 'not-polling', false],
+  ] as const)(
+    'maps a backend %s reason to %s',
+    async (failureReason, expectedPollingState, expectedTimedOut) => {
+      MockApiClient.addMockResponse({
+        url: `/organizations/${organization.slug}/seer/explorer-chat/42/`,
+        body: {
+          session: {
+            blocks: [],
+            failure_reason: failureReason,
+            status: 'error',
+            updated_at: new Date().toISOString(),
+          },
+        },
+      });
+
+      const {result} = renderHookWithProviders(
+        () => useSeerExplorerPolling({runId: 42}),
+        {organization}
+      );
+
+      await waitFor(() => {
+        expect(result.current.pollingState).toBe(expectedPollingState);
+      });
+      expect(result.current.isTimedOut).toBe(expectedTimedOut);
+    }
+  );
 });

static/app/views/seerExplorer/hooks/useSeerExplorerPolling.tsx

@@ -59,6 +59,9 @@ const getPollingState = (
     }
     return 'not-polling';
   }
+  if (sessionData?.failure_reason === 'timeout') {
+    return 'timed-out';
+  }
   if (isResponseComplete(sessionData)) {
     return 'not-polling';
   }

static/app/views/seerExplorer/types.tsx

@@ -234,6 +234,7 @@ export type SeerExplorerResponse = {
     blocks: Block[];
     status: 'processing' | 'completed' | 'error' | 'awaiting_user_input';
     updated_at: string;
+    failure_reason?: 'timeout' | 'stalled' | null;
     owner_user_id?: number | null;
     pending_user_input?: PendingUserInput | null;
     repo_pr_states?: Record<string, RepoPRState>;