I'd have thought it'd at least try, similar to how it does in when using my
sendmail host. My configuration remained the same, except for changing the
host to the machine running postfix instead.

The only thing I've noticed that was different is that instead of 554
(relaying denied), sendmail gave me a 550 instead. I was wondering if I've
misconfigured things such that it makes the mail client think it shouldn't
try to use that at all.
Below is the alpine logs for the sendmail equivalent for comparison -

IMAP DEBUG 11:01:57 5/13: EHLO hostname
IMAP DEBUG 11:01:57 5/13: 250-otherhost Hello hostname.domain [my ip],
pleased to meet you
IMAP DEBUG 11:01:57 5/13: 250-ENHANCEDSTATUSCODES
IMAP DEBUG 11:01:57 5/13: 250-PIPELINING
IMAP DEBUG 11:01:57 5/13: 250-8BITMIME
IMAP DEBUG 11:01:57 5/13: 250-SIZE 25000000
IMAP DEBUG 11:01:57 5/13: 250-DSN
IMAP DEBUG 11:01:57 5/13: 250-AUTH GSSAPI DIGEST-MD5 LOGIN PLAIN
IMAP DEBUG 11:01:57 5/13: 250-DELIVERBY
IMAP DEBUG 11:01:57 5/13: 250 HELP
Opened SMTP server "smtp.domain"
IMAP DEBUG 11:01:57 5/13: MAIL FROM:<user@domain>
IMAP DEBUG 11:01:57 5/13: 250 2.1.0 <user@domain>... Sender ok
IMAP DEBUG 11:01:57 5/13: RCPT TO:<user+test@domain>
IMAP DEBUG 11:01:57 5/13: 550 5.7.1 <user+test@domain>... Relaying denied.
Proper authentication required.
IMAP DEBUG 11:01:57 5/13: RSET
IMAP DEBUG 11:01:57 5/13: 250 2.0.0 Reset state
IMAP DEBUG 11:01:57 5/13: AUTH GSSAPI
IMAP DEBUG 11:01:57 5/13: 334
IMAP DEBUG 11:01:57 5/13: redacted
IMAP DEBUG 11:01:57 5/13: 334 redacted
IMAP DEBUG 11:01:57 5/13:
IMAP DEBUG 11:01:57 5/13: 334 redacted
IMAP DEBUG 11:01:57 5/13: redacted
IMAP DEBUG 11:01:57 5/13: 235 2.0.0 OK Authenticated
IMAP DEBUG 11:01:57 5/13: MAIL FROM:<user@domain>
IMAP DEBUG 11:01:57 5/13: 250 2.1.0 <user@domain>... Sender ok
IMAP DEBUG 11:01:57 5/13: RCPT TO:<user+test@domain>
IMAP DEBUG 11:01:57 5/13: 250 2.1.5 <user+test@domain>... Recipient ok
IMAP DEBUG 11:01:57 5/13: DATA

Maya

On Thu, 15 May 2025 at 19:14, Wietse Venema via Postfix-users <
postfix-users@postfix.org> wrote:

> Maya Copeland via Postfix-users:
> > IMAP DEBUG 14:17:19 5/15: 220 hostname ESMTP Postfix
> > IMAP DEBUG 14:17:19 5/15: EHLO desktop
> > IMAP DEBUG 14:17:19 5/15: 250-hostname
> > IMAP DEBUG 14:17:19 5/15: 250-PIPELINING
> > IMAP DEBUG 14:17:19 5/15: 250-SIZE 250000000
> > IMAP DEBUG 14:17:19 5/15: 250-VRFY
> > IMAP DEBUG 14:17:19 5/15: 250-ETRN
> > IMAP DEBUG 14:17:19 5/15: 250-AUTH GSSAPI DIGEST-MD5 LOGIN PLAIN
> > IMAP DEBUG 14:17:19 5/15: 250-ENHANCEDSTATUSCODES
> > IMAP DEBUG 14:17:19 5/15: 250-8BITMIME
> > IMAP DEBUG 14:17:19 5/15: 250-DSN
> > IMAP DEBUG 14:17:19 5/15: 250 CHUNKING
> > Opened SMTP server "hostname"
> > IMAP DEBUG 14:17:19 5/15: MAIL FROM:<user@domain>
> > IMAP DEBUG 14:17:19 5/15: 250 2.1.0 Ok
> > IMAP DEBUG 14:17:19 5/15: RCPT TO:<user+test@domain>
> > IMAP DEBUG 14:17:19 5/15: 554 5.7.1 <user+test@domain>: Relay access
> denied
> > IMAP DEBUG 14:17:19 5/15: RSET
> > IMAP DEBUG 14:17:19 5/15: 250 2.0.0 Ok
> > Mail not sent. Sending error: 554 One or more recipients failed
> > Send Error: "554 5.7.1 <user+test@domain>: Relay access denied"
> > IMAP DEBUG 14:17:19 5/15: QUIT
> > IMAP DEBUG 14:17:19 5/15: 221 2.0.0 Bye
> > call_mailer ERROR: Mail not sent: <user+test@domain>: Relay access
> denied
> > Send failed, continuing
>
> The Postfix SMTP server announces support for SASL mechanisms GSSAPI
> DIGEST-MD5 LOGIN and PLAIN, but the SMTP client does not send an
> AUTH command.  Therefore Postfix rejets the RCPT TO command.
>
> You need to configure the SMTP client to send an AUTH command.
>
>         Wietse
> _______________________________________________
> Postfix-users mailing list -- postfix-users@postfix.org
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>
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