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Devin Foley 13368c5183 fix: unblock clean-machine onboarding for api_key AI connections (nightly smoke) (#13372)
## Thinking Path

> - Paperclip is the open source app people use to manage AI agents for
work.
> - The release pipeline gates each nightly on a Docker onboarding
smoke. The smoke proves a clean machine can finish onboarding and hire
the first agent.
> - #13247, #13248, #13344, and #13351 changed the Connect step. Connect
now creates an AI connection that the server verifies live with the
provider.
> - The managed adoption check also demanded a CLI hello probe. A clean
machine has no provider CLI and cannot complete a subscription login.
Onboarding dead-ends and the nightly gate fails.
> - This pull request lets a live-verified API key adopt on the engine's
own verdict, and re-verifies the key with the provider at adoption time.
> - It also drives the release smoke through the API-key path against a
provider mock that lives inside the test harness.
> - The benefit is a green, deterministic release gate with no paid
credential in CI, and a working first run for API-key users on clean
installs.

## Linked Issues or Issue Description

No public issue exists. The failure surfaced in the nightly release
gate. Related PRs (no duplicates found): #13247, #13248, #13344, #13351
(the Connect changes), and #12423, #12135, #12151 (earlier release-smoke
updates).

**What happened?**

The nightly Release cut failed its gate: [run
34749840498](https://github.com/paperclipai/paperclip/actions/runs/34749840498),
job `smoke_nightly / smoke`, on published canary `2026.913.0-canary.2`.
The wizard never left the "Connect a model" step. The subscription path
waits for a human to run `claude auth login` on the server. The API-key
path saves and live-validates the key, but the environment test then
fails with `Command not found in PATH: "claude"` and
`ai_connection_validation_incomplete`, and the wizard blocks the hire.

**Expected behavior**

A clean machine with a provider-accepted API key completes onboarding
and hires the lead agent. The release smoke passes without a real paid
credential in CI.

**Steps to reproduce**

1. Run `scripts/docker-onboard-smoke.sh` with
`PAPERCLIPAI_VERSION=2026.913.0-canary.2`.
2. Sign in, complete onboarding to "Connect a model", select "Use API
key instead", pick Claude, enter a valid API key, and press Connect.
3. The environment test fails on the missing `claude` CLI and blocks the
hire.

**Paperclip version or commit**

`2026.913.0-canary.2` (nightly candidate `c9e3bb7ca`).

## What Changed

- `server/src/routes/agents.ts`: `testManagedEnvironment` no longer
forces the CLI-lane hello probe for a resolved `api_key` binding. It
re-verifies the key against the provider's live endpoint instead (the
same `validateAiApiKey` check the save performed, which needs no CLI). A
key the provider rejects fails adoption with
`ai_connection_api_key_rejected`. Subscription adoption keeps the strict
hello-probe requirement.
- `scripts/docker-onboard-smoke.sh`: the harness now serves
`api.anthropic.com` itself. A sibling container (the already-built smoke
image) runs a small HTTPS mock. The app container gets `--add-host` for
that one hostname and trusts the mock's certificate through
`NODE_EXTRA_CA_CERTS`. The private key stays mode 600 in the mock
container; the app container mounts only the certificate. The mock
serves only `GET /v1/models` and returns 404 for every other path.
`SMOKE_PROVIDER_MOCK=false` disables it.
- `tests/release-smoke/docker-auth-onboarding.spec.ts`: the spec drives
the API-key path — switch the credential mode before the source tile
(the link hides when the row collapses), enter the key, and Connect.
Loopback targets use a placeholder key that the mock accepts. Any other
target must set `PAPERCLIP_RELEASE_SMOKE_ANTHROPIC_API_KEY`, and the
test fails on arrival without it.
- `server/src/__tests__/agent-test-environment-routes.test.ts`: three
new route tests cover accepted keys (no CLI probe consulted),
provider-rejected keys, and subscriptions that cannot complete a hello
probe.

## Verification

- `npx vitest run src/__tests__/agent-test-environment-routes.test.ts` —
26/26 pass.
- `npx vitest run src/__tests__/ai-connections.test.ts
src/__tests__/ai-legacy-compatibility.test.ts` — 42/42 pass.
- `tsc --noEmit` reports no errors in the touched files.
- Full local harness + suite run against the exact failing canary: the
app container reaches the mock (request visible in the mock log), the
placeholder key validates, and the connection saves as the default. The
flow then stops at the forced CLI hello probe — the exact server check
this PR removes, still present in the published canary. The next canary
that includes this fix is the end-to-end proof.
- Hardening check: from inside the app container, the mock answers with
status 200 and `key.pem` is not visible.

## Risks

- Behavior shift: `api_key` adoption no longer requires a CLI hello
probe. It re-verifies the key with the provider at adoption instead.
Subscription adoption is unchanged.
- The mock returns 404 for unexpected provider calls, so a future
onboarding change that calls a new endpoint fails the smoke loudly
instead of passing silently.
- Release-smoke runs against non-loopback targets now require an
explicit key and fail fast without one.
- No database migration. No dependency change. No provider routing
change.

## Model Used

Claude Fable 5 (`claude-fable-5`) through the Claude Code CLI, with
extended thinking and tool use (shell, file edits, Playwright runs,
GitHub CLI). No other models were used.

## Checklist

- [x] I have included a thinking path that traces from project context
to this change
- [x] I have specified the model used (with version and capability
details)
- [x] I have checked ROADMAP.md and confirmed this PR does not duplicate
planned core work
- [x] I have searched GitHub for duplicate or related PRs and linked
them above
- [x] I have either (a) linked existing issues with `Fixes: #` / `Closes
#` / `Refs #` OR (b) described the issue in-PR following the relevant
issue template
- [x] I have not referenced internal/instance-local Paperclip issues or
links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip`
URLs)
- [x] My branch name describes the change (e.g. `docs/...`, `fix/...`)
and contains no internal Paperclip ticket id or instance-derived details
- [x] I have run tests locally and they pass
- [x] I have added or updated tests where applicable
- [x] I have updated relevant documentation to reflect my changes
- [x] I have considered and documented any risks above
- [x] All Paperclip CI gates are green
- [x] Greptile is 5/5 with no open P2s, recommendations, or follow-ups
- [x] I will address all Greptile and reviewer comments before
requesting merge
2026-09-13 17:02:02 -07:00
..
2026-03-09 10:03:45 -05:00
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