Files
docs/website/UPGRADE_NOTES.md
Claude 6f6b54a509 docs(website): §7 rewritten for SMTP, plus an upgrade-notes home
Engagement Phase 1's documentation (ENGAGEMENT.md §6.0b, row 1).

BACKEND_DESIGN.md §7 is REWRITTEN rather than amended, as the plan
requires: it documented Gmail OAuth2 as the mechanism. It now covers the
transport registry and why credentialFields is a single declaration
three consumers read, the credential blob and its fail-safe decrypt, the
no-phone-home rule and its CI guardrail, the three SMTP postures, why
Send test is the only verification left, the five failure contracts, and
the silent upgrade. The §2 tree, the PR-4 route-count note, the contact
row and the dashboard row are corrected alongside it — the dashboard now
returns warnings[].

UPGRADE_NOTES.md is new, and is the home for every later phase's
operator note as well (1b, 6, 10 and 13 each owe one). Newest first, and
scoped deliberately: an upgrade that needs nothing does not get an entry.
The entries worth writing are the ones that fail QUIETLY, which is
exactly what the Gmail removal does — mail stops, nothing errors, and
the only signal is a dashboard warning.

ENGAGEMENT.md records Phase 1 as built, with the four things that are
not what the plan says: only the transport half of §3.1 was built (a
channel nothing calls is a shape frozen too early), `enabled` now gates
every sender where it used to gate none of the direct ones, the G22
warning reads the deprecated column on purpose, and `npm run swagger`
had to be fixed first — the "per-file route limit" phases 8 and 9
recorded does not exist, and the real rule matters to every later phase
here, all of which add routes.

Co-Authored-By: Claude <noreply@anthropic.com>
2026-08-28 21:01:19 -05:00

4.4 KiB

Upgrade notes — website

Operator-facing. Newest first. One entry per change that requires an operator to do something, or that changes behaviour they would otherwise discover by accident.

Most upgrades need nothing: the schema is replayed on every boot with IF NOT EXISTS migrations, and a deployment that pulls a new image and restarts is done. This file exists for the exceptions — and the exceptions worth writing down are almost always the ones that fail quietly, because a loud failure announces itself and a quiet one does not.

Read the entries between the version you are on and the version you are moving to. Each names the action, whether it is required, and what happens if you do nothing.


Outbound email: the Gmail connect flow is gone; configure SMTP

Required, if this deployment currently sends email. Engagement Phase 1.

What changed

The "Connect Gmail" consent flow has been removed. Email now sends through an ordinary mail transport whose credentials an admin types in — SMTP is the baseline and the only transport shipped.

Removed with it: GET /api/v1/admin/email/connect/start, GET /api/v1/admin/email/connect/callback, and email's reuse of the google authentication provider's client id and secret. That reuse is worth a sentence of its own, because it was a coupling nobody could see: rotating the Google SSO secret silently broke outbound mail, with nothing on either screen relating the two. Single sign-on is otherwise unaffected — the google provider row exists for SSO in its own right and is untouched.

What you must do

On the first boot after the upgrade, email_config.transport backfills to smtp with no credentials. Until you supply some, no mail is sent — and nothing errors, because every sender is written to degrade politely:

  • the contact form falls back to a mailto: link,
  • an invite returns the accept link for you to send by hand,
  • a password reset still answers its usual generic success,
  • Team notifications are logged and dropped.

That is the risk this note exists for: email stops and nothing complains. The admin dashboard shows a warning while it is true, and the warning goes away by itself once a credential is saved.

Go to Admin → Settings → Email, choose the posture that fits, then use Send test — which is now the real verification of the whole configuration, not a formality.

Posture Settings Notes
A relay — recommended The relay's host, port 587, Implicit TLS off, your API key as the password Mailgun, SES, Postmark and equivalents. Reputation, DKIM and bounce handling are the relay's problem. The right answer for anything with volume
Gmail over SMTP — the shortest migration smtp.gmail.com, port 587, Implicit TLS off, your Google address as the username, and an app password This is the direct replacement for the removed connect flow. It needs an app password — 2-Step Verification must be on, and your ordinary account password will not work. Google's per-day send caps apply
Your own MTA Its host, port 25, Implicit TLS off, username and password left blank For an operator already running mail on the same host

Two fields cause most failures:

  • Implicit TLS is on only for port 465. On port 587 leave it off — the connection still upgrades to TLS, via STARTTLS. Port 587 with it on does not error; it hangs.
  • Send from is now typed by you rather than read back from Google, so nothing guarantees the server will accept it. It must be an address the account is allowed to send as, or the mail is refused for SPF/DMARC reasons that look like nothing at all. Send test names this specifically when it happens.

If you do nothing

Mail stays off. Nothing breaks and no data is lost — the site, the admin panel, logins, SSO and the shard integration all behave exactly as before. The dashboard warning stays up until you either configure a transport or press Clear credentials, which is how you say "this deployment deliberately sends no mail".

Data

Nothing is dropped. email_config gains transport, credential_enc and reply_to; the old provider and refresh_token_enc columns are kept but no longer read. Your stored Gmail refresh token is not used again and is cleared the first time you press Clear credentials.