fix(chat): validate restored contexts against send schema

apps/sim/app/o/[organizationId]/home/components/composer/composer.test.tsx

@@ -375,64 +375,81 @@ async function paste(files: File[]) {
   return event
 }
 
-it('keeps restored queued skills scoped when replacing a draft', async () => {
-  let restore: () => void = () => {}
-  function Harness() {
-    const [value, setValue] = useState('Original draft')
-    const [contexts, setContexts] = useState<ComponentProps<typeof Composer>['restoredContexts']>()
-    restore = () => {
-      setValue('/review fix this')
-      setContexts([
-        { kind: 'skill', skillId: 'skill-a', label: 'review', workspaceId: 'workspace-a' },
-      ])
+it.each([false, true])(
+  'keeps restored queued skills scoped and warns about lost context (%s)',
+  async (invalidContext) => {
+    let restore: () => void = () => {}
+    function Harness() {
+      const [value, setValue] = useState('Original draft')
+      const [contexts, setContexts] =
+        useState<ComponentProps<typeof Composer>['restoredContexts']>()
+      restore = () => {
+        setValue('/review fix this @Browser')
+        setContexts([
+          { kind: 'skill', skillId: 'skill-a', label: 'review', workspaceId: 'workspace-a' },
+          ...(invalidContext
+            ? [
+                {
+                  kind: 'browser_tab' as const,
+                  tabId: 'tab-a',
+                  label: 'Browser',
+                  selection: { text: 'Selected passage', title: 'x'.repeat(513) },
+                },
+              ]
+            : []),
+        ])
+      }
+      const files = useFileAttachments({
+        userId: 'user-a',
+        organizationId: 'organization-a',
+        requestMode: 'agent',
+      })
+      return (
+        <Composer
+          requestMode='agent'
+          value={value}
+          onChange={setValue}
+          restoredContexts={contexts}
+          files={files}
+          isInitialView={false}
+          isSending={false}
+          onStop={() => {}}
+          onSubmit={mocks.submit}
+        />
+      )
     }
-    const files = useFileAttachments({
-      userId: 'user-a',
-      organizationId: 'organization-a',
-      requestMode: 'agent',
-    })
-    return (
-      <Composer
-        requestMode='agent'
-        value={value}
-        onChange={setValue}
-        restoredContexts={contexts}
-        files={files}
-        isInitialView={false}
-        isSending={false}
-        onStop={() => {}}
-        onSubmit={mocks.submit}
-      />
+    await act(async () =>
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <FeatureFlagsProvider
+            flags={{
+              dashboards: false,
+              'workflow-tests': false,
+              changelog: false,
+              'mothership-model-selector': mocks.advanced,
+              'mothership-plan-mode': mocks.plan,
+            }}
+          >
+            <Harness />
+            <ToastProvider />
+          </FeatureFlagsProvider>
+        </QueryClientProvider>
+      )
     )
-  }
-  await act(async () =>
-    root.render(
-      <QueryClientProvider client={queryClient}>
-        <FeatureFlagsProvider
-          flags={{
-            dashboards: false,
-            'workflow-tests': false,
-            changelog: false,
-            'mothership-model-selector': mocks.advanced,
-            'mothership-plan-mode': mocks.plan,
-          }}
-        >
-          <Harness />
-        </FeatureFlagsProvider>
-      </QueryClientProvider>
+    await act(async () => restore())
+    expect(
+      container.querySelector<HTMLInputElement | HTMLTextAreaElement>('[aria-label="Ask Sim"]')!
+        .value
+    ).toBe('\u2003review fix this @Browser')
+    if (invalidContext) expect(document.body.textContent).toContain('Reattach it before sending.')
+    await act(async () =>
+      container.querySelector<HTMLButtonElement>('button[aria-label="Send"]')!.click()
     )
-  )
-  await act(async () => restore())
-  expect(
-    container.querySelector<HTMLInputElement | HTMLTextAreaElement>('[aria-label="Ask Sim"]')!.value
-  ).toBe('\u2003review fix this')
-  await act(async () =>
-    container.querySelector<HTMLButtonElement>('button[aria-label="Send"]')!.click()
-  )
-  expect(mocks.submit).toHaveBeenLastCalledWith('/review fix this', [
-    { kind: 'skill', skillId: 'skill-a', label: 'review', workspaceId: 'workspace-a' },
-  ])
-})
+    expect(mocks.submit).toHaveBeenLastCalledWith('/review fix this @Browser', [
+      { kind: 'skill', skillId: 'skill-a', label: 'review', workspaceId: 'workspace-a' },
+    ])
+  }
+)
 
 it('shows global built-ins once with no workspace label and submits no invented workspace', async () => {
   mocks.workspaces = []

apps/sim/app/o/[organizationId]/home/components/composer/composer.tsx

@@ -4,6 +4,7 @@ import { useEffect, useRef } from 'react'
 import { Chip, ComposerActionButton, cn, Tooltip, toast } from '@sim/emcn'
 import { ArrowUp, Paperclip, Plus, Search, Slash, StopFilled } from '@sim/emcn/icons'
 import { useQueries } from '@tanstack/react-query'
+import { UNAVAILABLE_CONTEXT_NOTICE } from '@/lib/mothership/chat/context'
 import {
   ASSISTANT_IMAGE_ACCEPT_ATTRIBUTE,
   isAssistantImageType,
@@ -153,7 +154,11 @@ export function Composer({
   useEffect(() => {
     if (!restoredContexts) return
     history.reset()
-    editorRef.current.restorePrompt(editorRef.current.getPlainValue(), restoredContexts)
+    const { hasUnavailableContexts } = editorRef.current.restorePrompt(
+      editorRef.current.getPlainValue(),
+      restoredContexts
+    )
+    if (hasUnavailableContexts) toast.info(UNAVAILABLE_CONTEXT_NOTICE)
   }, [restoredContexts, history.reset])
   useChatInputFocus({ textareaRef })
   const voice = useVoiceInput({

apps/sim/app/workspace/[workspaceId]/home/components/user-input/components/prompt-editor/use-prompt-editor.test.tsx

@@ -11,6 +11,8 @@ vi.mock('@/hooks/queries/skills', () => ({ useSkills: () => ({ data: [] }) }))
 vi.mock('@/hooks/queries/mcp', () => ({ useMcpToolServers: () => ({ data: [] }) }))
 vi.mock('@/blocks/integration-matcher', () => integrationMatcherMock)
 
+import { toDisplayMessage } from '@/lib/mothership/chat/display-message'
+import { normalizeMessage } from '@/lib/mothership/chat/persisted-message'
 import { SIM_SELECTION_MIME } from '@/lib/mothership/chat/selection-clipboard'
 import {
   type UsePromptEditorProps,
@@ -531,6 +533,51 @@ it('re-chipifies a seeded draft once skills load', () => {
 })
 
 describe('sent prompt history', () => {
+  it.each([
+    ['workspace ownership', { kind: 'file', fileId: 'file-a', workspaceId: 42 }],
+    [
+      'conflicting file owner',
+      {
+        kind: 'file',
+        fileId: 'file-a',
+        workspaceId: 'ws-1',
+        owner: { entityType: 'workspace', entityId: 'ws-2' },
+      },
+    ],
+    ['saved table view', { kind: 'table', tableId: 'table-a', viewId: ['view-a'] }],
+    ['empty browser selection', { kind: 'browser_tab', tabId: 'tab-a', selection: { text: '' } }],
+    [
+      'terminal selection bounds',
+      {
+        kind: 'terminal_tab',
+        terminalId: 'terminal-a',
+        selection: { text: 'output', startLine: 10_000_001, endLine: 10_000_002 },
+      },
+    ],
+  ])('recalls text and valid chips when saved %s is malformed', (_name, context) => {
+    const valid = { kind: 'file', fileId: 'file-b', label: 'Valid' }
+    const message = toDisplayMessage(
+      normalizeMessage({
+        id: 'stored',
+        role: 'user',
+        content: 'Compare @Invalid and @Valid',
+        contexts: [{ ...context, label: 'Invalid' }, valid],
+      })
+    )
+    const { result, unmount } = renderPromptEditor({ workspaceId: 'ws-1' })
+    try {
+      act(() => {
+        expect(
+          result().restorePrompt(message.content, message.contexts).hasUnavailableContexts
+        ).toBe(true)
+      })
+      expect(result().getPlainValue()).toBe('Compare @Invalid and @Valid')
+      expect(result().getActiveContexts()).toEqual([valid])
+    } finally {
+      unmount()
+    }
+  })
+
   it('recalls only user messages, walks both ways, and returns to the empty composer', () => {
     const history = renderHistoryEditor([
       { id: 'first', role: 'user', content: 'first\nsecond line' },

apps/sim/app/workspace/[workspaceId]/home/components/user-input/hooks/use-prompt-history.ts

@@ -4,6 +4,7 @@ import {
   getMothershipAttachmentPreviewUrl,
   getMothershipAttachmentUrl,
 } from '@/lib/mothership/chat/attachment-preview'
+import { UNAVAILABLE_CONTEXT_NOTICE } from '@/lib/mothership/chat/context'
 import type { PromptEditorInstance } from '@/app/workspace/[workspaceId]/home/components/user-input/components/prompt-editor/use-prompt-editor'
 import type { ChatMessage } from '@/app/workspace/[workspaceId]/home/types'
 import type { AttachedFile } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/copilot/components/user-input/hooks/use-file-attachments'
@@ -83,7 +84,7 @@ export function usePromptHistory(props: UsePromptHistoryProps) {
           message.contexts
         )
         if (hasUnavailableContexts) {
-          toast.info('Some context in this message was not saved. Reattach it before sending.')
+          toast.info(UNAVAILABLE_CONTEXT_NOTICE)
         }
         restoreAttachedFiles(files)
         editor.pendingCursorRef.current = direction === -1 ? 0 : value.length

apps/sim/app/workspace/[workspaceId]/home/components/user-input/user-input.tsx

@@ -15,6 +15,7 @@ import { Paperclip, Plus, Slash } from '@sim/emcn/icons'
 import { createLogger } from '@sim/logger'
 import { useParams } from 'next/navigation'
 import { getMothershipAttachmentPreviewUrl } from '@/lib/mothership/chat/attachment-preview'
+import { UNAVAILABLE_CONTEXT_NOTICE } from '@/lib/mothership/chat/context'
 import { MOTHERSHIP_ADD_CONTEXT_EVENT } from '@/lib/mothership/events'
 import { SIM_RESOURCE_DRAG_TYPE, SIM_RESOURCES_DRAG_TYPE } from '@/lib/mothership/resource-types'
 import { MOTHERSHIP_ACCEPT_ATTRIBUTE } from '@/lib/uploads/utils/validation'
@@ -370,7 +371,8 @@ const UserInputImpl = forwardRef<UserInputHandle, UserInputProps>(function UserI
       loadQueuedMessage: (msg: QueuedMessage) => {
         const currentEditor = editorRef.current
         history.reset()
-        currentEditor.restorePrompt(msg.content, msg.contexts)
+        const { hasUnavailableContexts } = currentEditor.restorePrompt(msg.content, msg.contexts)
+        if (hasUnavailableContexts) toast.info(UNAVAILABLE_CONTEXT_NOTICE)
         const restored: AttachedFile[] = (msg.fileAttachments ?? []).map((a) => ({
           id: a.id,
           name: a.filename,

apps/sim/app/workspace/[workspaceId]/home/hooks/send-handoff.test.ts

@@ -1,7 +1,11 @@
 /** @vitest-environment jsdom */
 import { beforeEach, expect, it } from 'vitest'
+import { MAX_CHAT_CONTEXTS } from '@/lib/mothership/chat/context-limits'
 import { STREAM_STORAGE_KEY } from '@/lib/mothership/constants'
-import { readQueuedSendHandoffState, writeQueuedSendHandoffState } from './send-handoff'
+import {
+  readQueuedSendHandoffState,
+  writeQueuedSendHandoffState,
+} from '@/app/workspace/[workspaceId]/home/hooks/send-handoff'
 
 beforeEach(() => sessionStorage.clear())
 const seed = () => ({
@@ -33,3 +37,76 @@ it('rejects invalid levels and preserves an explicit Build mode', () => {
   writeQueuedSendHandoffState({ ...seed(), requestMode: 'agent' })
   expect(readQueuedSendHandoffState()).toMatchObject({ requestMode: 'agent' })
 })
+
+it('keeps lost-context evidence when a recovered handoff is written again', () => {
+  const validContext = { kind: 'docs' as const, label: 'Docs' }
+  writeQueuedSendHandoffState({
+    ...seed(),
+    contexts: [
+      validContext,
+      {
+        kind: 'browser_tab',
+        tabId: 'tab-a',
+        label: 'Browser',
+        selection: { text: 'Selected passage', title: 'x'.repeat(513) },
+      },
+    ],
+  })
+  const recovered = readQueuedSendHandoffState()
+  expect(recovered).toMatchObject({ contexts: [validContext], hasUnavailableContexts: true })
+  if (!recovered) throw new Error('Expected a recoverable handoff')
+  writeQueuedSendHandoffState(recovered)
+  expect(readQueuedSendHandoffState()).toMatchObject({
+    contexts: [validContext],
+    hasUnavailableContexts: true,
+  })
+})
+
+it.each([null, {}, 'invalid'])(
+  'keeps the message for review when stored contexts are malformed (%s)',
+  (contexts) => {
+    sessionStorage.setItem(
+      `${STREAM_STORAGE_KEY}:queued-send-handoff`,
+      JSON.stringify({ ...seed(), contexts })
+    )
+    expect(readQueuedSendHandoffState()).toMatchObject({
+      message: 'Search',
+      hasUnavailableContexts: true,
+    })
+  }
+)
+
+it.each([100, 101])(
+  'recovers %s contexts within the send limit without losing review state',
+  (count) => {
+    const contexts = Array.from({ length: count }, (_, index) => ({
+      kind: 'file' as const,
+      fileId: `file-${index}`,
+      label: `File ${index}`,
+    }))
+    writeQueuedSendHandoffState({ ...seed(), contexts })
+    const recovered = readQueuedSendHandoffState()
+    expect(recovered?.contexts).toEqual(contexts.slice(0, MAX_CHAT_CONTEXTS))
+    expect(recovered?.message).toBe('Search')
+    expect(recovered?.hasUnavailableContexts).toBe(count > MAX_CHAT_CONTEXTS ? true : undefined)
+    if (!recovered) throw new Error('Expected a recoverable handoff')
+    writeQueuedSendHandoffState(recovered)
+    expect(readQueuedSendHandoffState()).toEqual(recovered)
+  }
+)
+
+it('keeps a full limit of valid contexts when an earlier stored context is invalid', () => {
+  const contexts = Array.from({ length: MAX_CHAT_CONTEXTS }, (_, index) => ({
+    kind: 'file' as const,
+    fileId: `file-${index}`,
+    label: `File ${index}`,
+  }))
+  sessionStorage.setItem(
+    `${STREAM_STORAGE_KEY}:queued-send-handoff`,
+    JSON.stringify({
+      ...seed(),
+      contexts: [{ kind: 'workspace', label: 'Missing address' }, ...contexts],
+    })
+  )
+  expect(readQueuedSendHandoffState()).toMatchObject({ contexts, hasUnavailableContexts: true })
+})

apps/sim/app/workspace/[workspaceId]/home/hooks/send-handoff.ts

@@ -1,4 +1,5 @@
 import { isChatContext } from '@/lib/mothership/chat/context'
+import { MAX_CHAT_CONTEXTS } from '@/lib/mothership/chat/context-limits'
 /**
  * Queued-send handoff (revamp M6 extraction, behavior-preserving): the sessionStorage
  * claim machinery that carries a queued outgoing message across a chat-scope handoff —
@@ -35,6 +36,7 @@ export interface QueuedSendHandoffState extends QueuedSendHandoffSeed {
   message: string
   fileAttachments?: FileAttachmentForApi[]
   contexts?: ChatContext[]
+  hasUnavailableContexts?: boolean
   requestMode?: ChatRequestMode
   assistantSearch?: WorkspaceSearchFilters
   assistantSearchLevel?: AssistantSearchLevel
@@ -108,6 +110,14 @@ export function readQueuedSendHandoffState(): QueuedSendHandoffState | null {
     const assistantSearch = workspaceSearchFiltersSchema.safeParse(parsed.assistantSearch ?? {})
     if (!assistantSearch.success) return null
 
+    const contexts = Array.isArray(parsed.contexts)
+      ? parsed.contexts.filter(isChatContext).slice(0, MAX_CHAT_CONTEXTS)
+      : undefined
+    const hasUnavailableContexts =
+      parsed.hasUnavailableContexts === true ||
+      (parsed.contexts !== undefined &&
+        (!Array.isArray(parsed.contexts) || contexts?.length !== parsed.contexts.length))
+
     return {
       id: parsed.id,
       ...(chatId ? { chatId } : {}),
@@ -123,9 +133,8 @@ export function readQueuedSendHandoffState(): QueuedSendHandoffState | null {
       ...(Array.isArray(parsed.fileAttachments)
         ? { fileAttachments: parsed.fileAttachments.filter(isFileAttachmentForApi) }
         : {}),
-      ...(Array.isArray(parsed.contexts)
-        ? { contexts: parsed.contexts.filter(isChatContext) }
-        : {}),
+      ...(contexts ? { contexts } : {}),
+      ...(hasUnavailableContexts ? { hasUnavailableContexts: true } : {}),
       ...(parsed.requestMode === 'assistant' ||
       parsed.requestMode === 'agent' ||
       parsed.requestMode === 'plan'