Summary

Fixes #80468.

Cron direct announce delivery could successfully send a message to a channel while leaving the destination channel session transcript unaware of that assistant message. Later sessions_history reads from the channel session could therefore miss cron reports that the user had already received in chat.

This PR updates isolated cron direct delivery to:

• resolve the outbound destination session before sending
• ensure the resolved session entry exists for first-contact outbound deliveries
• append the successfully delivered assistant output into that destination session transcript
• keep the transcript mirror best-effort so mirror failures do not turn successful delivery into a failed cron run
• avoid duplicate main-session records when cron awareness queueing is already the intended main-session record
• skip deleteAfterRun cleanup for non-cron session keys

It also tightens fallback outbound session classification for resolver-less channels: plugin-owned target parsing wins first, and core only handles explicit semantic prefixes like user:, channel:, and group:.

Related: #74913 covers adjacent cron transcript mirroring work for a narrower session:<id> path. This PR covers destination channel-session mirroring for cron direct announce delivery.

Real behavior proof

• Behavior or issue addressed:
  Cron direct announce delivery to a WhatsApp DM should be visible in that WhatsApp DM session transcript / sessions_history.

• Real environment tested:
  macOS mac-mini running OpenClaw installed from the PR branch tarball at SHA 97c6640688 (openclaw-2026.5.10-beta.1.tgz, built via pnpm install --frozen-lockfile && pnpm run build && pnpm pack). WhatsApp channel enabled, cfg.session.dmScope = "per-channel-peer". Base release before the swap: [email protected].

• Exact steps or command run after this patch:

  # Install fix tarball (built locally via `pnpm pack` from the PR branch)
  npm install -g ./openclaw-2026.5.10-beta.1.tgz
  
  # Beta-channel migration only — this box came from [email protected] stable.
  # NOT a fix requirement; needed because `2026.5.10-beta.1` externalised the codex
  # plugin from the bundled extensions/ tree. Skip on a clean beta install that
  # already has @openclaw/codex resolved.
  openclaw plugins install @openclaw/codex
  
  # Restart gateway
  launchctl unload ~/Library/LaunchAgents/ai.openclaw.gateway.plist
  launchctl enable gui/$(id -u)/ai.openclaw.gateway
  launchctl bootstrap gui/$(id -u) ~/Library/LaunchAgents/ai.openclaw.gateway.plist
  
  # Create one-shot synthetic cron with a unique recognizable token
  openclaw cron add \
    --name "REPRO-after-fix" \
    --agent main --announce \
    --channel whatsapp --to "+15551234567" \
    --account default --session isolated \
    --session-key "agent:main:whatsapp:direct:+15551234567" \
    --at "1m" --delete-after-run --light-context --thinking low \
    --timeout-seconds 60 --tools exec \
    --message "...emit exactly REPRO_TOKEN_AFTER_FIX_7a4611d7..."
  
  # After cron finishes: verify run log + grep destination session
  jq '{status,delivered,deliveryStatus,delivery,summary,sessionKey}' \
    ~/.openclaw/cron/runs/<cron-id>.jsonl
  
  grep -c "REPRO_TOKEN_AFTER_FIX_7a4611d7" \
    ~/.openclaw/agents/main/sessions/<wa-dm-session-id>.jsonl

• Evidence after fix:

  OpenClaw version / package source:

  $ jq -r '.name + "@" + .version' /Users/<redacted>/.npm-global/lib/node_modules/openclaw/package.json
  [email protected]
  # installed from ./openclaw-2026.5.10-beta.1.tgz built at SHA 97c6640688
  

  Synthetic token used: REPRO_TOKEN_AFTER_FIX_7a4611d7

  Cron run succeeded + WhatsApp delivery succeeded from ~/.openclaw/cron/runs/<job-id>.jsonl:

  {
    "status": "ok",
    "delivered": true,
    "deliveryStatus": "delivered",
    "delivery": {
      "resolved": {
        "ok": true,
        "channel": "whatsapp",
        "to": "+15551234567",
        "accountId": "default",
        "source": "explicit"
      },
      "fallbackUsed": true,
      "delivered": true
    },
    "summary": "REPRO_TOKEN_AFTER_FIX_7a4611d7",
    "sessionKey": "agent:main:cron:<job-id>:run:<worker-id>"
  }

  sessions_history / direct transcript grep finds the token in the resolved WhatsApp DM session:

  $ grep -c "REPRO_TOKEN_AFTER_FIX_7a4611d7" \
      ~/.openclaw/agents/main/sessions/<wa-dm-session-id>.jsonl
  1
  

  The single entry, inspected:

  ts=2026-05-11T22:07:48
  type=message  role=assistant
  text: REPRO_TOKEN_AFTER_FIX_7a4611d7
  

  The DM session id corresponds to session key agent:main:whatsapp:direct:+15551234567, the resolved destination session, not the isolated cron worker session.

• Observed result after fix:
  The fresh token delivered by cron appears in the destination WhatsApp DM session transcript as a role=assistant mirror entry. Hit count is 1, versus 0 hits in the same session under the before-fix stable repro on [email protected], where the identical synthetic cron token was present only in the cron run log and the auto-deleted isolated worker session.

• What was not tested:
  Other channels (Discord, Telegram, Slack) and dmScope: "main" / non-per-channel-peer setups were not live-tested on this box. They are covered by targeted unit/seam tests in src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts and src/infra/outbound/outbound-session.test.ts.

• Before evidence:
  Cron-delivered messages not visible in channel session context #80468 (comment) — same shape of synthetic cron on [email protected] produced delivered: true with 0 hits of the unique token in the same destination DM session jsonl.

Root Cause

• Root cause:
  Cron direct announce delivery sent outbound payloads using the cron run session context without appending the successfully delivered assistant output into the resolved destination channel session transcript.

• Missing detection / guardrail:
  Existing tests covered successful delivery and awareness queueing, but did not assert that explicit channel cron delivery mirrors into the destination session used by later sessions_history reads.

• Contributing context:
  Main-session awareness is a separate system-event path and does not replace the destination channel transcript entry for per-channel-peer DM sessions.

Regression Test Plan

• Coverage level that should have caught this:

  • Seam / integration test

• Target test or file:
  src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts and src/infra/outbound/outbound-session.test.ts

• Scenario the test should lock in:
  Isolated cron direct announce delivery resolves the destination channel session, bootstraps the session entry when needed, and appends the delivered assistant text to that destination session only after successful delivery.

• Why this is the smallest reliable guardrail:
  It exercises the cron dispatch/outbound-session seam without requiring live channel credentials, while the live proof above verifies the real WhatsApp behavior end to end.

User-visible / Behavior Changes

Cron direct announce messages are now visible in the destination channel session transcript after successful delivery, so later turns on that channel can see what the cron job sent.

Security Impact

• New permissions/capabilities? No
• Secrets/tokens handling changed? No
• New/changed network calls? No
• Command/tool execution surface changed? No
• Data access scope changed? No

Verification

• Before-fix live repro on [email protected]: synthetic cron delivery reached WhatsApp, but the fresh token had 0 hits in the WhatsApp DM session transcript.
• After-fix live proof above: synthetic cron delivery reached WhatsApp and the fresh token had 1 hit in the resolved WhatsApp DM session transcript as role=assistant.
• pnpm test src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts src/infra/outbound/outbound-session.test.ts -- --reporter=verbose
• pnpm exec oxfmt --check --threads=1 src/cron/isolated-agent/delivery-dispatch.ts src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts src/infra/outbound/outbound-session.ts src/infra/outbound/outbound-session.test.ts src/infra/outbound/outbound-session.test-helpers.ts
• git diff --check
• pnpm check:changed