Environment

• OpenClaw: pre-restart version unknown; the next gateway that came up was 2026.5.4 (same install, auto-restart from update path). The shutdown SyntaxError fired on the old process being torn down.
• Backend: gateway process running under systemd-user (openclaw-gateway.service), invoked as op run --env-file=... -- node .../openclaw/dist/index.js gateway --port 18789
• Node.js: bundled with the published npm package
• Plugins enabled: anthropic, browser, canvas, device-pair, file-transfer, memory-core, phone-control, slack, talk-voice, telegram (10 total)
• Host: single-VPS Linux deployment (hostname redacted), no container

TL;DR

During an auto-restart triggered by the openclaw update path, the outgoing gateway process fails to shut down cleanly because a dynamic import is looking up an export named 'r' from synthetic-auth.runtime.js that no longer exists. The single-letter export name strongly suggests a minified/mangled identifier — either a build-bundling collision or a stale artifact in the installed package. Co-occurs with a separate bug (see related issue below) to produce a 96-minute user-visible outage.

Symptom

A single line in the gateway journal at shutdown:

[gateway] shutdown error: SyntaxError: The requested module
'./synthetic-auth.runtime.js' does not provide an export named 'r'

Same shutdown also kills any in-flight cli-backend turn with a FailoverError:

[agent/cli-backend] claude live session turn failed:
  provider=claude-cli model=claude-opus-4-7
  durationMs=91970 error=FailoverError
[model-fallback/decision] model fallback decision:
  decision=candidate_failed
  requested=claude-cli/claude-opus-4-7
  candidate=claude-cli/claude-opus-4-7
  reason=unknown next=claude-cli/claude-sonnet-4-6
  detail=Claude CLI failed.

The new gateway then comes up successfully and reports all plugins listening:

[gateway] http server listening (10 plugins: anthropic, browser, canvas,
  device-pair, file-transfer, memory-core, phone-control, slack, talk-voice,
  telegram; 6.5s)

So the SyntaxError is contained to the shutdown path of the outgoing process — the new process starts fine.

Hypothesis

'r' as an export name is almost never written by hand — it strongly suggests a mangled identifier left over from a minifier/bundler pass. Likely causes, in rough order of probability:

1. Cross-bundle mangle-collision. synthetic-auth.runtime.js is built with one minifier pass that produces export { ... as r }, and a separate consumer bundle was built with a different pass that imports 'r' by name. If the runtime bundle was rebuilt at some point without re-minifying the consumer, the names drift and the import fails.
2. Stale installed artifact. The update path replaced one bundle but not its peer — the consumer is from a newer version, the runtime is from an older one (or vice versa).
3. Side-effect of dynamic vs static import(). The shutdown path may be calling import('./synthetic-auth.runtime.js') dynamically, which defers the export-name check until runtime, allowing the mismatch to ship undetected.

Repro

Not deterministically reproduced. Triggered automatically during an auto-restart along the update path. The local restart log shows the prior trigger:

[YYYY-MM-DDTHH:MM:SSZ] openclaw restart attempt source=update target=openclaw-gateway.service
[YYYY-MM-DDTHH:MM:SSZ] openclaw restart done source=update

This is the first time we've seen the SyntaxError specifically — prior restarts on this host have been clean.

Impact (in isolation)

By itself: low. The shutdown error doesn't prevent the new gateway from starting, and the only in-flight casualty is whatever turn was running at the moment of restart.

In combination with the lazy harness-registration bug filed in a peer issue (see below): high. Together they produced a 96-minute window where every inbound message hit MissingAgentHarnessError and the user got a generic "Something went wrong" reply.

Ask

1. Audit the bundler/minifier config for synthetic-auth.runtime.js and its consumers — confirm export names are either stable (not minified) or are minified consistently across all bundles in a single build.
2. Consider statically importing synthetic-auth.runtime.js so any export-name mismatch surfaces at build time, not at shutdown.
3. Add a sanity check at install/update time that verifies all internal modules can resolve their declared imports (cheap: a smoke import at end of npm postinstall).
4. Independently of the fix, make the shutdown path tolerant — shutdown error: ... should not be the only signal; a follow-up "shutdown completed (with N errors)" line would make this easier to spot in journals.

Related

• Co-occurred 2026-05-24 with a separate MissingAgentHarnessError bug — filed as a peer issue, linked from there.