Commit Graph
2 Commits
Author SHA1 Message Date
ekklesiaandClaude Opus 5 3563549e86 fix: let a deployment name itself in the SMTP greeting
CI / verify (pull_request) Successful in 42s
CI / infrastructure-smoke (pull_request) Successful in 20s
CI / migration-smoke (pull_request) Successful in 1m41s
A real deployment could not send mail through an IP-authorized relay.
Every attempt surfaced as MAIL_PROVIDER_UNAVAILABLE while the relay was
healthy and swaks sent from the same machine.

The cause was the greeting, and it is generic rather than tied to any
provider. An SMTP client identifies itself in EHLO, and with nothing
configured Nodemailer derives that from the machine hostname —
substituting the address literal [127.0.0.1] whenever the hostname is
not fully qualified, which is the normal state of a container. The relay
closed the connection on it with a 421 before any message was offered,
which is indistinguishable from the relay being down.

EKKLESIA_SMTP_HELO_NAME now lets the deployment say what to greet as. It
is validated as a fully qualified domain name — no scheme, port,
brackets, whitespace, or control characters, and at least one dot, since
a single unqualified label is exactly the input Nodemailer already
discards. It is not a credential: it travels in the clear on every
connection, so Doctor prints it where an operator can compare it against
what the relay expects, and Doctor's probe performs the same greeting the
runtime does.

Absent preserves Nodemailer's behaviour exactly. It is deliberately not
defaulted to the sender's domain: a machine whose hostname is already a
valid FQDN may be greeting correctly, and some relays check that against
reverse DNS, so replacing it silently would trade one deployment's bug
for another's.

The regression guard is a raw SMTP server that refuses any greeting but
the expected one, because smtp-server exposes no EHLO hook and its
earliest hook is never reached by a send-nothing probe.

Co-Authored-By: Claude Opus 5 <[email protected]>
2026-08-25 20:28:30 -05:00
ekklesiaandClaude Opus 5 fa3021e49b feat: add a host-provided outbound email transport
CI / verify (pull_request) Successful in 42s
CI / infrastructure-smoke (pull_request) Successful in 21s
CI / migration-smoke (pull_request) Successful in 1m23s
Ekklesia could authenticate people and pair devices but could not send a
single message. Better Auth has been configured with emailAndPassword
since ADR 0011 and neither of its mail hooks — sendResetPassword and
emailVerification.sendVerificationEmail — was ever implemented, so email
verification, password recovery, and invitations were all blocked on the
same missing thing.

That missing thing is a transport, not a Google Workspace integration.
Email is now a host-provided infrastructure service with a provider seam,
shaped exactly like object storage: feature code says "send this
transactional message" and the provider owns the host, port, TLS,
credentials, connection behaviour, and every transport error. No
provider's hostname appears anywhere in Core, and a test asserts it.
Google Workspace SMTP Relay is the expected first deployment and a
compatibility target — the same variables address Microsoft 365, a
transactional provider, or a local Postfix.

The contract is deliberately tiny: one recipient or a small bounded list,
a subject, text and/or HTML, an optional reply-to, and nothing else. There
is no `from` field at all — the sender is host configuration, so no
feature and no future module can choose who mail appears to come from,
which is how a platform otherwise acquires an impersonation primitive.
Control characters are refused rather than stripped in addresses, display
names, subjects, and reply-to values; writing that rule down was not
enough, because the first implementation trimmed an address before
checking it and silently accepted a trailing carriage return until a test
caught it.

Security modes are named rather than inferred from a boolean and a port,
which is genuinely ambiguous: `secure: false` on 587 means "connect in the
clear and hope STARTTLS is offered". `starttls` sets requireTLS so a
stripped upgrade fails the send instead of continuing in plaintext,
production refuses `plaintext` outright, and certificate verification has
no off switch. Credentials are optional as a pair, because a relay
authorized by source IP has neither and requiring them would make the
intended production arrangement unconfigurable; half a pair fails loudly.

Connection, greeting, and socket timeouts are all explicit — the
object-storage pass already showed what a network client on library
defaults does to a request. Nothing retries: a failure after the message
data has gone out is ambiguous, and retrying it turns one password-reset
request into several emails, so this is a single bounded attempt and
deliberately not an exactly-once promise.

Email stays optional. An installation with no SMTP host is a complete
deployment, nothing sends at startup, and constructing the transport opens
no socket. There is no POST /api/v1/send-email and no route that touches
the provider — an authenticated send endpoint is an open relay with extra
steps. Modules get nothing either; services are added one at a time when
something real needs one, and nothing does yet.

Proven against a real in-process SMTP server rather than a mock: delivery
with the host's sender on the wire, authentication and its sanitized
refusal, a rejected mailbox distinguished from an outage, a refused
connection, a silent server hitting its deadline, and a starttls transport
refusing to continue when the upgrade is not offered. No test sends real
email and no live credential exists in this repository or in CI.

Co-Authored-By: Claude Opus 5 <[email protected]>
2026-08-24 18:37:16 -05:00