SMTP: implicit TLS (port 465) support + fix quarantined mail
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Two real fixes to app/mail.py, both found by testing against an actual
mail server rather than just a fake stub:

- Replaces the STARTTLS-only smtp_use_tls boolean with a three-way
  smtp_encryption ("none"/"starttls"/"ssl"). Implicit TLS (port 465,
  what Purelymail and most providers offer alongside 587/STARTTLS) is a
  different handshake entirely -- TLS from the first byte, not a
  plaintext connection that gets upgraded -- so it needs its own
  smtplib.SMTP_SSL code path, not just a skipped starttls() call.
  Schema migration v3 adds the column, backfills it from the old
  boolean, and drops the boolean (safe on a live, populated DB).

- Outgoing mail was missing Date and Message-ID headers -- email.mime
  doesn't set either automatically, and a missing Message-ID in
  particular is enough for a strict content filter (confirmed via a
  real Postfix+Amavis mail server's logs: SPF/DKIM/DMARC all passed
  cleanly, but Amavis quarantined the message as "BAD-HEADER-0" purely
  for the missing id) to silently swallow an otherwise-legitimate
  email, even though smtplib reports success -- the send genuinely
  succeeds to the relay, it just never survives the recipient's own
  filtering. Both headers are now set, with the Message-ID's domain
  matching the From address.

Verified: SMTP_SSL path against a hand-rolled implicit-TLS fake server
(self-signed cert, client-side verification relaxed only in the test
harness -- production code keeps ssl.create_default_context()'s real
verification), the v2->v3 migration against live data, the full admin
SMTP-save + test-email round trip over HTTP, and the standing legacy-
device curl suite.
This commit is contained in:
2026-07-22 01:07:50 -04:00
parent 8e10ca540e
commit c1c803b497
5 changed files with 58 additions and 14 deletions
+5 -1
View File
@@ -218,7 +218,11 @@ class ServerSettings(Base):
smtp_username: Mapped[str] = mapped_column(String, default="")
smtp_password: Mapped[str] = mapped_column(String, default="")
smtp_from_address: Mapped[str] = mapped_column(String, default="")
smtp_use_tls: Mapped[bool] = mapped_column(Boolean, default=True)
# "none" (plaintext, port 25 typically), "starttls" (upgrades a
# plaintext connection, port 587 typically), or "ssl" (TLS from the
# first byte -- a different handshake entirely, not just starttls()
# skipped; port 465 typically). See app/mail.py.
smtp_encryption: Mapped[str] = mapped_column(String, default="starttls")
class PasswordResetToken(Base):