On 2025-05-15 at 14:53:47 UTC-0400 (Thu, 15 May 2025 19:53:47 +0100)
Maya Copeland via Postfix-users <m...@maya.cx>
is rumored to have said:

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.

It is not reliable or even reasonable to expect a MUA to try authentication only after an attempt to send without authentication fails. Configure your MUA to authenticate by default and your problem should go away.

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.

There's no sound reason for a MUA to react differently to a 554 or 550 in response to a RCPT. It is not normal for a MUA to attempt to submit mail without authentication. It's 2025, not 1992.




--
 Bill Cole
 b...@scconsult.com or billc...@apache.org
(AKA @grumpybozo@toad.social and many *@billmail.scconsult.com addresses)
 Not Currently Available For Hire
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