Hello,

[email protected] (Reio Remma), 2018.09.04 (Tue) 21:51 (CEST):
> I've a backup script in Windows that sends an e-mail upon completion.
> The mail goes out successfully if I use port 25 on the mail server but fails
> unspectacularly with no specific error message on OpenSMTPD side when I try
> to submit it authenticated on port 587.

I had to remove the rest, it contained info you should not have posted
and should change now ;-)

client: AUTH login <[email protected]>
server: 334 Usernamu: [I have no idea why the *u is there!]
client: (answers with a string that does not look like a username)
server: [thinks it's got a username] 334 Password:
client: disconnects

IIRC, there's two ways of doing auth in SMTP, your client is trying A
and smtpd expecting B.

Marcus

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