postfix/smtp[5046]: connect to smtp-mail.outlook.com[65.55.176.126]:587: Connection timed out

klm_spitfire · 3. März 2017

Hey everyone!

I could really use some help. I've been trying to configure server notifications, but keep running into issues with connectivity along the way.

My current SMTP settings are as follows:

SMTP server = smtp-mail.outlook.com
SMTP port = 587
Use SSL/TLS secure connection = true
Sender email = john.doe@outlook.com
Authentication required = true
Username = john.doe@outlook.com

Every time I click the 'Send a test email' nothing is received. Upon inspecting the the system logs, I consistently find the following type of messages:

Code

Mar  2 21:11:43 openmediavault postfix/pickup[3752]: 130C4620910: uid=0 from=<root>
Mar  2 21:11:43 openmediavault postfix/cleanup[5044]: 130C4620910: message-id=<20170303021143.130C4620910@openmediavault.localdomain>
Mar  2 21:11:43 openmediavault postfix/qmgr[3753]: 130C4620910: from=<john.doe@outlook.com>, size=487, nrcpt=1 (queue active)
Mar  2 21:12:13 openmediavault postfix/smtp[5046]: connect to smtp-mail.outlook.com[65.55.176.126]:587: Connection timed out
Mar  2 21:12:13 openmediavault postfix/smtp[5046]: 130C4620910: to=<my.personal.email@gmail.com>, relay=none, delay=31, delays=0.28/0.15/30/0, dsn=4.4.1, status=deferred (connect to smtp-mail.outlook.com[65.55.176.126]:587: Connection timed out)
Mar  2 21:12:25 openmediavault postfix/qmgr[3753]: 8D145620923: from=<john.doe@outlook.com>, size=487, nrcpt=1 (queue active)

I tried troubleshooting the issue by running 'dig' and 'ping' against outlook, but I'd be lying if I said I fully knew what I was doing. At the very least, I'm able to say with confidence that I can successfully ping 'smtp.outlook.com' from OMV.

If anyone could help me, I'd super appreciate it! Thanks!

Dropkick Murphy · 3. März 2017

Works here so far...

Code

telnet smtp-mail.outlook.com 587

leads to:

Code

220 BLU437-SMTP4.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Fri, 3 Mar 2017 02:35:07 -0800


530 5.7.0 Must issue a STARTTLS command first


quit
221 2.0.0 BLU437-SMTP4.smtp.hotmail.com Service closing transmission channel

Watch line 3. Any STARTTLS avail in your settings?

HTH

Edit: I remember I had a problem with that stuff, too...other provider, but try to use IP instead of name. In your case enter 65.55.163.152 and try again...

klm_spitfire · 3. März 2017

Thanks for the response, I think you've helped me narrow down the issue. Since I didn't have telnet installed on OMV, I tried telnet-ing into smtp-mail.outlook.com from my laptop.

The response I got was:

Code

Trying 65.55.163.126...
telnet: connect to address 65.55.163.126: Operation timed out
telnet: Unable to connect to remote host

I then connected to my roommate's network (same provider) and telnet-ed again... This time, the response was:

Code

Trying 65.55.163.152...
Connected to smtp.glbdns2.microsoft.com.
Escape character is '^]'.
220 BLU437-SMTP77.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Fri, 3 Mar 2017 13:31:50 -0800 
quit
221 2.0.0 BLU437-SMTP77.smtp.hotmail.com Service closing transmission channel
Connection closed by foreign host.

I then reconnected to my personal network, and attempted "telnet 65.55.163.152 587". Same type of response as before:

Code

telnet 65.55.163.152 587
Trying 65.55.163.152...
telnet: connect to address 65.55.163.152: Operation timed out
telnet: Unable to connect to remote host

It seems like the issue might not be with OMV, but with my router configuration :/.

klm_spitfire · 5. März 2017

Any advice?

Jetzt mitmachen!