(SOLVED) test email could not be sent: Connection unexpectedly closed: The read operation timed out

[dudemanbacon]

I have been running FreeNAS at home since v8. I have had email notifications working the entire time until sometime within the last month or so, when they just stopped arriving in my email box (probably after I upgraded last, I'm not sure what that version was). I had not had time to look at it until tonight and I found that I'm getting this error, "Your test email could not be sent: Connection unexpectedly closed: The read operation timed out" on both of my FreeNAS servers.

I found this bug posting: https://bugs.freenas.org/issues/7104.
I updated both servers to FreeNAS-9.3-STABLE-201511040813 and it did not fix the issue.
Email settings:
From email: root@deathstar.local (also tried my email hotmail address)
Outgoing mail server: smtp.live.com
Port: 25 (I tried 587 and 465 as well)
TLS/SSL: TLS (tried SSL and plain)
Username: username@hotmail.com
Password: mypassword

Any ideas on this one?

Thanks in advance,
Nick

 

[dudemanbacon]

I'm not seeing anything in the mail logs either:

[root@deathstar] /var/log# tail maillog
Nov 10 00:00:00 deathstar newsyslog[75760]: logfile turned over

[root@deathstar] /var/log# tail maillog.0
Nov 9 00:00:00 deathstar newsyslog[23881]: logfile turned over
Nov 10 00:00:00 deathstar newsyslog[75760]: logfile turned over

I see this in the messages log:

Nov 10 23:29:43 deathstar manage.py: [common.system:210] Failed to send email: Connection unexpectedly closed: The re ad operation timed out


Thanks,
Nick

 

[dlavigne]

Sounds like a DNS error... Anything change in the network?

 

[dudemanbacon]

Thanks for the response. I don't know why I didn't think of that, but yes, I did just replace my router and switch with a Cisco Meraki security appliance and switch. Either way, I just realized that the emails are all showing up in my "Sent" items in my email account, so it doesn't appear to be a FreeNAS issue. They must be getting blocked somewhere because they are coming from the same address or something. I'll have to look into it.

 

[dudemanbacon]

I'm a bit confused about what happened here, because the default settings were working fine, but I was able to fix this by changing the "from email" to my hotmail email address, instead of deathstar@freenas.local.