Release 0.18.0: email + webhook hygiene (roadmap items #18 + #20)

VERSION + frontend/package.json -> 0.18.0. CHANGELOG entry with
the binding Upgrade-steps block per SPEC.md §20.4.

This release lands all five slices of the v0.18.0 proposal at
~/git/ohm-infra/RFC-APP-EMAIL-HYGIENE-PROPOSAL.md:

  Slice 1: build_envelope helper + unit tests.
  Slice 2: migrate send paths; add POST /api/email/unsubscribe
           for RFC 8058 one-click.
  Slice 3: mandatory GITEA_WEBHOOK_SECRET (+ dev-bypass) +
           unknown-repo logging.
  Slice 4: outbound_emails audit table + admin endpoint.
  Slice 5: bounce correlation via Message-ID.

Full suite: 295 passed (was 252 pre-release).

Upgrade-steps (RFC 2119) block in CHANGELOG covers:
  * MUST: GITEA_WEBHOOK_SECRET non-empty at startup.
  * MAY: RFC_APP_INSECURE_WEBHOOKS=1 for local dev only.
  * MAY: EMAIL_UNSUBSCRIBE_MAILTO to route opt-out courtesy mail
         to a different mailbox than EMAIL_FROM.
  * MUST: apply migration 020_outbound_emails.sql (auto-applied
          on next start; no operator action).
  * MUST: rebuild frontend + restart backend.
  * SHOULD: run mail-tester.com probe post-upgrade.
This commit is contained in:
Ben Stull
2026-05-28 07:39:33 -07:00
parent 4666c4abe7
commit 0562d53f86
3 changed files with 186 additions and 2 deletions
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@@ -23,6 +23,190 @@ skip versions are the composition of each intervening adjacent
release's steps in order — no A-to-B path is pre-computed beyond
that.
## 0.18.0 — 2026-05-28
**Minor — schema migration required; one env var now mandatory; no
new secrets.** This release lands the framework-side half of OHM
roadmap items #18 (Secure the SMTP relay + Gitea webhook) and #20
(Email deliverability). It is the framework counterpart to the
operator-side SMTP / DNS hardening covered in the
`EMAIL-AND-WEBHOOK-HARDENING-RUNBOOK.md` companion doc.
The release is shipped in five atomic slices per the v0.18.0 proposal:
1. **`build_envelope` shared helper.** A single place where every
outbound `EmailMessage` is constructed. Lands the
deliverability-critical headers (`Date`, `Message-ID`,
`Auto-Submitted`) uniformly across OTC, invite, watcher
notification, bundle, and digest paths; exposes per-kind
unsubscribe semantics (none for OTC, mailto: for invites, full
one-click for bulk-adjacent paths) as explicit kwargs.
2. **Migrated send paths.** `email_otc.py`, `email_invite.py`,
`email._deliver`, `email._send_bundle`, and `digest.py` now
build their envelopes through the helper. Per-RFC invite
(v0.16.0) rides through `email_invite.py`'s helper and picks
up the change for free. The shared `_SENT` test buffer also
carries the constructed `EmailMessage` under `envelope["message"]`
so tests can assert on the header surface directly.
3. **Webhook handler tightening.** `GITEA_WEBHOOK_SECRET` is now
mandatory at startup — the framework refuses to load_config()
if it's empty, unless the operator explicitly opts into the
dev-bypass with `RFC_APP_INSECURE_WEBHOOKS=1`. The
`/api/webhooks/gitea` receiver carries defense-in-depth checks
that surface the misconfiguration loudly at the request layer
too. Mis-targeted webhooks (a hook on a fork or a stale Gitea
binding) now log at INFO instead of silently 200-OK'ing.
4. **`outbound_emails` audit table + admin endpoint.** Every send
helper writes one row to `outbound_emails` before returning,
capturing the send attempt regardless of outcome
(status='sent' / 'failed' / 'deferred'). The new admin endpoint
`GET /api/admin/outbound-emails` (filterable by kind / status /
to_address) lets the operator answer "did this person ever get
their invite?" without grepping VM logs. No admin UI ships
with v0.18.0; operator queries via curl + jq for now.
5. **Bounce correlation.** The `POST /api/webhooks/email-bounce`
body accepts a new optional `message_id` field; when supplied,
the handler stamps status='bounced' on the matching
`outbound_emails` row and returns the row id as
`correlated_id`. The pre-existing hard-bounce ->
`email_opt_out_all = 1` flow still fires.
The `POST /api/email/unsubscribe` endpoint also lands in Slice 2
as the matching receiver for the new `List-Unsubscribe-Post:
List-Unsubscribe=One-Click` header (Gmail and Yahoo POST that
payload on the user's one-click action per RFC 8058 — the GET
endpoint alone is no longer sufficient for senders at OHM's tier).
### Added
- **`backend/app/email_envelope.py`** — the `build_envelope` helper.
Single source of truth for every outbound `EmailMessage`'s
headers + body shape. Standalone module so tests can exercise it
without booting the FastAPI app.
- **`backend/migrations/020_outbound_emails.sql`** — the audit
table. Single new table with three indexes (to_address, sent_at,
message_id); no changes to existing tables.
- **`email.record_outbound(...)`** — best-effort write helper every
send path calls. Catches `RuntimeError` (so pure-helper unit
tests where `db.init()` was never called don't break) and any
other exception (so the audit write never breaks a send).
- **`GET /api/admin/outbound-emails`** in `api_admin.py`
admin-only listing of `outbound_emails`. Newest-first, filterable
by kind, status, and to_address (case-insensitive). Returns
`{items: [...], has_more}` per the rest of the admin endpoints'
shape.
- **`POST /api/email/unsubscribe`** in `api_notifications.py`
RFC 8058 one-click receiver. Accepts the same `?t=` token as the
GET handler; idempotent; returns 200 + `{ok, category}` on
success.
- **`all` synthetic category** for unsubscribe URLs. Used by the
bundle + digest paths (which can't honor per-category opt-outs
because they span multiple categories); flips
`email_opt_out_all = 1` rather than a per-category column.
### Changed
- **`backend/app/email.py`** — `EmailConfig` gains
`unsubscribe_mailto` (env: `EMAIL_UNSUBSCRIBE_MAILTO`, default
falls back to `EMAIL_FROM`). `_deliver` and `_send_bundle`
build envelopes through `build_envelope` and thread `kind` +
`notification_id` into the audit write.
- **`backend/app/email_otc.py`** + **`email_invite.py`** — both
call `build_envelope` and `record_outbound`. OTC carries no
`List-Unsubscribe` (recipient explicitly requested the code);
invite carries `List-Unsubscribe: <mailto:…>` only (no signed
URL — the invitee isn't a user yet, no per-user opt-out row
exists).
- **`backend/app/digest.py`** — calls `_deliver` with `kind='digest'`
+ the new `all`-category one-click unsubscribe.
- **`backend/app/webhooks.py`** — refuses 500 at request time if
the secret is empty + bypass isn't set; logs a loud warning
per-request when running under the bypass; logs INFO when a
hook targets a repo not in `cached_rfcs`.
- **`backend/app/config.py`** — `load_config()` raises
RuntimeError if `GITEA_WEBHOOK_SECRET` is empty unless
`RFC_APP_INSECURE_WEBHOOKS=1`.
- **`backend/app/api_notifications.py`** — GET unsubscribe handler
accepts the `all` category (sets `email_opt_out_all = 1`).
Bounce webhook body adds optional `message_id` field; response
shape adds `correlated_id` field. (Tests that read the exact
response shape — currently just
`test_bounce_webhook_refuses_unsigned_when_secret_configured`
in test_e2e_smoke.py — updated to assert on the new shape.)
- **`backend/tests/test_propose_vertical.py`** — the shared
`tmp_env` fixture binds a fake `GITEA_WEBHOOK_SECRET` so all
252 pre-v0.18.0 tests boot cleanly under the new mandatory
secret. Tests that want to exercise the dev-bypass path
monkeypatch `RFC_APP_INSECURE_WEBHOOKS=1` explicitly.
### Tests
- 15 new unit tests in `test_email_envelope.py` for the helper.
- 10 new integration tests across `test_otc_vertical`,
`test_admin_create_user_invite_vertical`, and
`test_notifications_vertical` covering: OTC has no
List-Unsubscribe; invite has mailto: only; notification has
full one-click; POST one-click flips per-category; `all` flips
global; respects `EMAIL_UNSUBSCRIBE_MAILTO` override.
- 7 new integration tests in `test_webhooks_vertical.py` covering
the startup-time mandatory-secret check, the dev-bypass, and
the request-time signature verification including the unknown-
repo log line.
- 11 new integration tests in `test_outbound_emails_vertical.py`
covering the audit table write path (OTC / invite / notification),
the admin endpoint (list, filter by kind, filter by to_address,
non-admin refusal), and the bounce correlation (matched
message_id stamps status='bounced'; unknown message_id is
logged; absent message_id falls back to legacy behavior; bounced
rows surface in admin endpoint with `?status=bounced`).
- One test updated for intentional response-shape change:
`test_e2e_smoke.test_bounce_webhook_refuses_unsigned_when_secret_configured`.
Full suite: 295 passed (was 252 pre-v0.18.0).
### Migration
- **`backend/migrations/020_outbound_emails.sql`** — auto-applied
on next backend start. Single new table with three indexes; no
changes to existing tables.
### Upgrade steps (from 0.17.0)
- Operators **MUST** ensure `GITEA_WEBHOOK_SECRET` is set in the
deployment's env. The framework now refuses to start if it's
empty. (For OHM-flotilla deployments,
`flotilla secret list <deployment>` confirms the binding; OHM
has carried this binding since v0.14.0, so the upgrade is
gesture-free for OHM specifically.)
- Operators **MAY** set `RFC_APP_INSECURE_WEBHOOKS=1` to bypass
the requirement in local-dev environments. Production
deployments **MUST NOT** set this; if they do, every webhook
POST logs a loud warning line per request.
- Operators **MAY** set `EMAIL_UNSUBSCRIBE_MAILTO` to route
`List-Unsubscribe: <mailto:…>` opt-out courtesy mail to a
humans-monitored mailbox distinct from the no-reply
`EMAIL_FROM` sender. Default falls back to `EMAIL_FROM`.
- You **MUST** apply schema migration
`020_outbound_emails.sql`. The migration creates a single new
table with three indexes; the framework runs migrations
automatically at process start, so no manual step is required
beyond restarting the backend so the migration runner picks
the file up. Existing deployments pick it up on first start
after upgrade with no operator action required.
- You **MUST** rebuild the frontend and restart the backend
after upgrading. `frontend/package.json#version` and `VERSION`
both move to `0.18.0`. No new secrets (the `outbound_emails`
table writes synchronously to the same SQLite file as every
other write).
- Operators **SHOULD** run a `mail-tester.com` probe against the
upgraded deployment to confirm the new envelope headers
(`Date`, `Message-ID`, `Auto-Submitted`, `List-Unsubscribe`,
`List-Unsubscribe-Post`) land cleanly with the upstream SMTP
relay's DKIM signing. The expected delta from pre-v0.18.0 is
+2-3 points on the spam-score axis (typical 5-6/10 baseline
→ 9+/10 post-upgrade).
## 0.17.0 — 2026-05-28
**Minor — schema migration required; no new env vars; no new secrets.**
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0.17.0
0.18.0
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{
"name": "rfc-app-frontend",
"private": true,
"version": "0.17.0",
"version": "0.18.0",
"type": "module",
"scripts": {
"dev": "vite",