Hi 
I would check Firewall in Windows for port 587 outbound or temporarily turn it 
off and test it again. 

Nino

> On 5 Sep 2018, at 5:52 am, Reio Remma <r...@mrstuudio.ee> wrote:
> 
> 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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