fix(web): preserve failed inactive send prompts

[oodavy41]

Summary

Preserve the user’s prompt when sending to an inactive/invalid session fails during session resolution/resume.

Previously, if resolveSessionId failed before the send mutation started, the composer had already cleared the input, so a 500/502 resume/send failure could make the user’s prompt disappear with no visible recovery path.

Changes

• On resolveSessionId failure before send, append a failed optimistic user bubble containing the original prompt.
• Keep the prompt visible/copyable/retryable instead of losing it.
• Preserve scheduledAt and attachments in the failed bubble metadata/content.
• Update retry behavior so failed preserved prompts re-run resolveSessionId before sending.
• Restore failed status if retry-time resolution fails.
• Add regression coverage for:
  • failed resolve preserving a prompt bubble;
  • retry resolving an inactive session before sending;
  • scheduled retry still preserving scheduledAt.

Notes

Known pre-existing limitation: retrying a failed bubble does not currently re-send attachments. This PR preserves attachments visually in the failed bubble but does not change the broader retry attachment behavior.

Validation

• git diff --check origin/main..HEAD
• bun typecheck
• bun --cwd web test src/hooks/mutations/useSendMessage.test.tsx
• env -u HAPI_CLI_EXECUTABLE bun run test

Full suite passed.

[github-actions]

Findings

• [Major] Retried preserved prompts drop attachments — resolve failure now creates a failed bubble with attachments, but the new retry path calls mutation.mutate without carrying those attachments forward. api.sendMessage therefore receives undefined for attachments, so a preserved image/file prompt retries as text-only; attachment-only preserved prompts also remain non-retryable because the retry guard rejects empty originalText. Evidence web/src/hooks/mutations/useSendMessage.ts:226.
  Suggested fix:

  const message = findMessageByLocalId(sessionId, localId)
  if (!message) return false
  
  const content = message.content
  const userContent = content
      && typeof content === 'object'
      && 'role' in content
      && (content as { role?: unknown }).role === 'user'
      && 'content' in content
      ? (content as { content?: unknown }).content
      : undefined
  const attachments = userContent
      && typeof userContent === 'object'
      && 'attachments' in userContent
      ? (userContent as { attachments?: AttachmentMetadata[] }).attachments
      : undefined
  const originalText = message.originalText ?? ''
  if (!originalText && !attachments?.length) return false
  
  mutation.mutate({
      sessionId: targetSessionId,
      text: originalText,
      localId,
      createdAt: message.createdAt,
      attachments,
      scheduledAt: message.scheduledAt ?? null,
  })

Questions

• None.

Summary

• Review mode: initial
• One regression found in the new preserved-prompt retry path. Add coverage for text+attachment and attachment-only preserved resolve failures so retry behavior matches the bubble the user sees.

Testing

• Not run (automation): bun --cwd web test src/hooks/mutations/useSendMessage.test.tsx failed here because bun is not on PATH (/bin/bash: bun: command not found).

HAPI Bot

[github-actions]

[MAJOR] Retrying a prompt preserved by the new resolve-failure path drops its attachments. createOptimisticMessage now stores attachments in the failed bubble, but this retry mutation does not pass them back to api.sendMessage, so image/file prompts get retried as text-only; attachment-only prompts are still rejected by the originalText guard.

Suggested fix:

const message = findMessageByLocalId(sessionId, localId)
if (!message) return false

const content = message.content
const userContent = content
    && typeof content === 'object'
    && 'role' in content
    && (content as { role?: unknown }).role === 'user'
    && 'content' in content
    ? (content as { content?: unknown }).content
    : undefined
const attachments = userContent
    && typeof userContent === 'object'
    && 'attachments' in userContent
    ? (userContent as { attachments?: AttachmentMetadata[] }).attachments
    : undefined
const originalText = message.originalText ?? ''
if (!originalText && !attachments?.length) return false

mutation.mutate({
    sessionId: targetSessionId,
    text: originalText,
    localId,
    createdAt: message.createdAt,
    attachments,
    scheduledAt: message.scheduledAt ?? null,
})

[github-actions]

Findings

• [Major] Retried preserved prompts still drop attachments — this PR now stores attachments in the failed optimistic bubble when inactive-session resolution fails, but the retry mutation only sends originalText. A text+file prompt retries as text-only, and an attachment-only prompt is still blocked by the originalText guard, even though the user sees the attachment preserved in the failed bubble. Evidence web/src/hooks/mutations/useSendMessage.ts:226.
  Suggested fix:

  const message = findMessageByLocalId(sessionId, localId)
  if (!message) return false
  
  const userContent = message.content?.role === 'user'
      ? message.content.content
      : undefined
  const attachments = userContent?.type === 'text'
      ? userContent.attachments
      : undefined
  const originalText = message.originalText ?? ''
  if (!originalText && !attachments?.length) return false
  
  mutation.mutate({
      sessionId: targetSessionId,
      text: originalText,
      localId,
      createdAt: message.createdAt,
      attachments,
      scheduledAt: message.scheduledAt ?? null,
  })

Questions

• None.

Summary

• Review mode: follow-up after new commits
• The prior attachment retry issue is still present in the latest diff. The new tests cover text-only preserved retries and scheduled retry metadata, but not text+attachment or attachment-only preserved prompts.

Testing

• Not run (automation/security): review only; did not execute PR code.

HAPI Bot

[github-actions]

[MAJOR] Retrying a prompt preserved by the new resolve-failure path still drops its attachments. createOptimisticMessage stores attachments in the failed bubble, but this retry mutation does not pass them back to api.sendMessage; text+file prompts retry as text-only, and attachment-only prompts are rejected by the originalText guard.

Suggested fix:

const message = findMessageByLocalId(sessionId, localId)
if (!message) return false

const userContent = message.content?.role === 'user'
    ? message.content.content
    : undefined
const attachments = userContent?.type === 'text'
    ? userContent.attachments
    : undefined
const originalText = message.originalText ?? ''
if (!originalText && !attachments?.length) return false

mutation.mutate({
    sessionId: targetSessionId,
    text: originalText,
    localId,
    createdAt: message.createdAt,
    attachments,
    scheduledAt: message.scheduledAt ?? null,
})