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ekklesiaandClaude Opus 5 3563549e86
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fix: let a deployment name itself in the SMTP greeting
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

11 KiB

Outbound email

Ekklesia can send transactional email through a host-configured SMTP transport (ADR 0037).

Two things send email: email verification and password recovery (ADR 0038). Invitations do not exist.

An installation with no SMTP configured is still a complete, valid deployment — the platform starts, every existing feature works, and the initial platform owner can sign in. What it cannot do is verify a new account or recover a password, because both need a message to arrive. See When no relay is configured.

Configuring a relay

variable meaning
EKKLESIA_SMTP_HOST A bare hostname or IP. Absent means this installation sends no email. Never a URL, port, or connection string.
EKKLESIA_SMTP_PORT Optional; defaults to the conventional port for the security mode.
EKKLESIA_SMTP_SECURITY implicit-tls, starttls (default), or plaintext.
EKKLESIA_SMTP_USERNAME / EKKLESIA_SMTP_PASSWORD Optional as a pair. Half a pair is refused.
EKKLESIA_SMTP_FROM_ADDRESS Required once a host is set. The only address this platform can send as.
EKKLESIA_SMTP_FROM_NAME Optional display name.
EKKLESIA_SMTP_HELO_NAME Optional. The name this client announces in EHLO. See When a relay refuses the connection.

Security modes are explicit

A boolean plus a port is ambiguous — "connect in the clear and hope STARTTLS is offered" is a plaintext session waiting to happen. Naming the mode removes the ambiguity:

  • implicit-tls — TLS from the first byte, conventionally port 465.
  • starttls — plaintext connect then a required upgrade, conventionally 587 (or 25 on a relay). If the server does not offer STARTTLS the send fails rather than continuing in the clear. This is the default and what most relays expect.
  • plaintext — no TLS. Development and trusted local relays only; production refuses it.

Certificate verification is always on and there is no setting that turns it off.

When a relay refuses the connection

If a relay closes the connection before accepting anything — a 421, or an MAIL_PROVIDER_UNAVAILABLE from a relay you can reach perfectly well with another client — suspect the greeting before suspecting the network.

An SMTP client has to identify itself in the EHLO command, and Ekklesia does not invent that name. With nothing configured, Nodemailer derives it from the machine's own hostname, and substitutes the address literal [127.0.0.1] whenever that hostname is not fully qualified — which is the normal state of a container, or of a VM nobody has named. A relay that requires a resolvable client identity rejects that greeting outright, and because the rejection lands before any message is offered it is indistinguishable from the relay being down.

This was a real deployment defect, and a generic one: the relay worked, swaks sent from the same machine, and only the greeting differed.

C: EHLO [127.0.0.1]
S: 421-4.7.0 Try again later, closing connection. (EHLO)

Set the name explicitly:

EKKLESIA_SMTP_HELO_NAME=example.org
C: EHLO example.org
S: 250 ...

Use a fully qualified domain name the deployment owns, typically its sending domain. The value is validated at startup: no scheme, no port, no brackets, no whitespace, no trailing dot, and at least one label plus a domain — a single unqualified name such as localhost is refused, because that is exactly the input Nodemailer already discards.

It is not a credential. It travels in the clear on every connection, so it appears in pnpm doctor output where an operator can check it against what the relay expects.

Leaving it unset preserves Nodemailer's own behaviour exactly. It is deliberately not defaulted to the sender's domain: a machine whose hostname is a valid FQDN may already be greeting correctly — some relays check the greeting against the connecting address's reverse DNS — and silently replacing a working identity would trade one deployment's bug for another's.

Google Workspace SMTP Relay

The expected first production deployment, and a compatibility target rather than a dependency — no provider hostname appears anywhere in Ekklesia's code.

EKKLESIA_SMTP_HOST=<the relay host shown in Google Workspace Admin>
EKKLESIA_SMTP_PORT=587
EKKLESIA_SMTP_SECURITY=starttls
EKKLESIA_SMTP_FROM_ADDRESS=[email protected]
EKKLESIA_SMTP_FROM_NAME=Ekklesia

Whether that relay also needs EKKLESIA_SMTP_USERNAME and EKKLESIA_SMTP_PASSWORD depends entirely on how the relay is authorized in Google Workspace Admin, which varies per deployment. Google supports authorizing by source IP range, by SMTP authentication, or both, and the setting also controls which envelope senders are accepted.

A Google relay does not accept mail anonymously from an arbitrary internet host. If the deployment relies on IP authorization, the server's egress address has to be registered, and a change of hosting provider or NAT address will break sending until it is updated.

Such a relay is also likely to require a fully qualified EHLO name — this is the deployment that exposed the generic issue described in When a relay refuses the connection — so EKKLESIA_SMTP_HELO_NAME is usually needed alongside the variables above.

The same variables address Microsoft 365, a transactional provider's SMTP endpoint, a local Postfix, or anything else that speaks the protocol. Switching between them is configuration, not code.

The sender is host-owned

There is deliberately no way for feature code to choose a sender. A message has no from field at all; EKKLESIA_SMTP_FROM_ADDRESS is the only address this platform can send as. Letting features pick a sender is how a platform acquires an impersonation primitive and ruins its own domain reputation.

Deliverability is a deployment concern this repository cannot verify for you: publish SPF, DKIM, and DMARC records for the sending domain, and make sure the relay is authorized to send as that address.

Secrets

EKKLESIA_SMTP_PASSWORD is a deployment secret, handled like every other one (ADR 0029): never stored in PostgreSQL, never routed through module configuration, never returned by any route, never printed by Doctor, and never included in an error. .env.example documents the variable and deliberately carries no value.

What the transport does and does not promise

  • One bounded attempt, no retry. A failure after the message data has gone out is ambiguous — the server may have accepted it and only the acknowledgement was lost — so retrying would turn one password-reset request into several emails. send resolving means the next hop accepted responsibility, not that anyone received anything. There is no outbox and no exactly-once guarantee.
  • Bounded connection, greeting, and socket timeouts. A silent server returns a structured MAIL_PROVIDER_UNAVAILABLE rather than hanging.
  • A tiny contract. One recipient or a small bounded list, a subject, text and/or HTML, and an optional reply-to. No attachments, headers, CC, BCC, templates, or bulk sending.
  • Header injection is refused. Carriage returns, line feeds, and other control characters in addresses, display names, subjects, and reply-to values are rejected rather than stripped.

Diagnostics

pnpm doctor reports outbound-email.configuration as one of:

  • skipped — no host configured. A complete deployment.
  • pass — connected, and authenticated where credentials are set. It sent nothing.
  • warning — configured but did not answer. A warning rather than a failure, because nothing depends on mail yet and some relays decline a connection that sends no message.
  • failure — the settings are structurally invalid, reported as a sanitized code with no credential.

A successful probe proves the relay accepts this deployment. It does not prove a message would reach an inbox — that depends on the relay's authorization policy and the domain's DNS records.

Doctor reads the EKKLESIA_SMTP_* values through the same loadHostConfiguration the API executable uses, so the relay it reports on is the relay the runtime would use. The check is rendered in Doctor's own Outbound email section.

Logging

Transactional email carries verification links, reset links, and personal data. The transport logs nothing. Features built on it should log at most that a send was attempted, the provider's message id, and an error category — never a body, a subject, or a verification or reset link.

Testing

core/tests/mail-smtp.integration.test.ts runs a real in-process SMTP server (smtp-server) and proves message delivery, the host-owned sender on the wire, authentication and its refusal, a rejected mailbox, 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.

What the platform actually sends

message when contents
Verify your Ekklesia email address a new account signs in unverified, or asks for a resend one link, an expiry sentence, and ignore-if-unexpected wording
Reset your Ekklesia password someone asks to recover an account one link, an expiry sentence, and a note that the current password still works

Both are plain text and HTML, both are generic Ekklesia templates with no branding and no marketing content, and both are built in core/src/identity/notifications.ts — which knows a recipient, a subject, and two bodies, and nothing about SMTP.

Links are rebuilt from validated configuration rather than taken from the request that triggered them, so no caller can steer where a recipient lands. They point at EKKLESIA_DASHBOARD_ORIGIN (defaulting to the identity base URL). See Identity.

When no relay is configured

Nothing crashes and nothing changes shape. A verification or recovery request answers exactly as it would with a working relay — the response must not reveal whether an account exists, and it must not start revealing it the moment SMTP breaks — and the operator is told out of band:

[identity] password-reset email was not delivered: MAIL_NOT_CONFIGURED

That line carries a flow and a sanitized code. It never carries the address, the token, or the link. pnpm doctor reports the same absence under outbound-email.configuration.

The operator requirement is therefore:

  • normal production use of verification and recovery → requires configured outbound email
  • initial platform-owner bootstrap (pnpm identity:create-initial-owner) → does not