Hello!

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 suspect it's a PowerShell issue, but just in case, here are OpenSMTPD logs from the attempt.

IIRC authenticated submission used to work with our old QMail server.

PowerShell merely states:

Send-MailMessage : Authentication failed.
+ Send-MailMessage @param
+ ~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : InvalidOperation: 
(System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpException
    + FullyQualifiedErrorId : 
SmtpException,Microsoft.PowerShell.Commands.SendMailMessage

Regular OpenSMTPD logs state:

Sep  4 22:21:33 host smtpd[1011]: 676cdf15bd475b2d smtp event=connected 
address=10.0.8.2 host=10.0.8.2
Sep  4 22:21:34 host smtpd[1011]: 676cdf15bd475b2d smtp event=starttls address=10.0.8.2 
host=10.0.8.2 ciphers="version=TLSv1.2, cipher=ECDHE-RSA-AES256-GCM-SHA384, 
bits=256"
Sep  4 22:21:34 host smtpd[1011]: 676cdf15bd475b2d smtp event=closed 
address=10.0.8.2 host=10.0.8.2 reason=disconnect


OpenSMTPD with trace states:

Sep  4 22:28:12 host smtpd[28824]: 1358b9537a51618f smtp event=starttls address=10.0.8.2 
host=10.0.8.2 ciphers="version=TLSv1.2, cipher=ECDHE-RSA-AES256-GCM-SHA384, 
bits=256"
Sep  4 22:28:12 host smtpd[28824]: mproc: pony -> control : 41 
IMSG_STAT_INCREMENT
Sep  4 22:28:12 host smtpd[28824]: smtp: 0x239f1a0: STATE_TLS -> STATE_HELO
Sep  4 22:28:12 host smtpd[28822]: imsg: control <- pony: IMSG_STAT_INCREMENT 
(len=41)
Sep  4 22:28:12 host smtpd[28822]: ramstat: increment: smtp.tls
Sep  4 22:28:12 host smtpd[28822]: ramstat: smtp.tls (0x2193800): 0 -> 1
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_DATAIN <io:0x23a0470 fd=16 
to=300000 fl=R ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=15 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: <<< EHLO Silencio
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: STATE_HELO -> STATE_HELO
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-host.domain.ee 
Hello Silencio [10.0.8.2], pleased to meet you
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-8BITMIME
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-ENHANCEDSTATUSCODES
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-SIZE 104857600
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-DSN
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250-AUTH PLAIN LOGIN
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 250 HELP
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_LOWAT <io:0x23a0470 fd=16 
to=300000 fl=W ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=0 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_DATAIN <io:0x23a0470 fd=16 
to=300000 fl=R ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=37 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: <<< AUTH login 
cmVpb0BtcnN0dXVkaW8uZWX=
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: STATE_HELO -> 
STATE_AUTH_USERNAME
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 334 VXNlcm5hbXU6
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_LOWAT <io:0x23a0470 fd=16 
to=300000 fl=W ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=0 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_DATAIN <io:0x23a0470 fd=16 
to=300000 fl=R ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=18 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: <<< OGlyNW1GTnp6eg==
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: STATE_AUTH_USERNAME -> 
STATE_AUTH_PASSWORD
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: >>> 334 UGFzc3dvcmQ6
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_LOWAT <io:0x23a0470 fd=16 
to=300000 fl=W ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=0 ob=0>
Sep  4 22:28:13 host smtpd[28824]: smtp: 0x239f1a0: IO_DISCONNECTED <io:0x23a0470 
fd=16 to=300000 fl=R ssl=TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256 ib=0 ob=0>
Sep  4 22:28:13 host smtpd[28824]: 1358b9537a51618f smtp event=closed 
address=10.0.8.2 host=10.0.8.2 reason=disconnect


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