[SOLVED] Email notifications not working on Ubuntu

[Ashpool]

Sonarr version: 2.0.0.4389
Mono version: 4.2.3 (Stable 4.2.3.4/832de4b Wed Mar 16 13:19:08 UTC 2016)
OS: Ubuntu 16.04.1 LTS

When attempting to setup an email notification I get a connection timeout. On the same machine Couchpotato is able to send emails using the same connection details and credentials. I can also telnet to the smtp server OK.
I wonder mono could be at fault. Are there any other ubuntu users out there who have configured email successfully?
thanks

[v2.0.0.4389] System.Net.Mail.SmtpException: Message could not be sent. —> System.Net.Sockets.SocketException: Connection timed out
at System.Net.Sockets.TcpClient.Connect (System.Net.IPAddress[] ipAddresses, Int32 port) <0x40a369d0 + 0x00337> in :0
at System.Net.Sockets.TcpClient.Connect (System.String hostname, Int32 port) <0x40a36700 + 0x0002f> in :0
at System.Net.Sockets.TcpClient…ctor (System.String hostname, Int32 port) <0x40a366d0 + 0x00017> in :0
at System.Net.Mail.SmtpClient.SendInternal (System.Net.Mail.MailMessage message) <0x40a36320 + 0x0006f> in :0
at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) <0x40a36060 + 0x00113> in :0
— End of inner exception stack trace —
at System.Net.Mail.SmtpClient.Send (System.Net.Mail.MailMessage message) <0x40a36060 + 0x001cb> in :0
at NzbDrone.Core.Notifications.Email.EmailService.Send (System.Net.Mail.MailMessage email, System.String server, Int32 port, Boolean ssl, System.Net.NetworkCredential credentials) <0x40a35110 + 0x000a7> in :0
at NzbDrone.Core.Notifications.Email.EmailService.SendEmail (NzbDrone.Core.Notifications.Email.EmailSettings settings, System.String subject, System.String body, Boolean htmlBody) <0x40a33d30 + 0x001ff> in :0

16-11-10 22:03:59.1|Warn|NzbDroneErrorPipeline|Invalid request Validation failed:
– Unable to send test email

[markus101]

The connection is timing out, so the SMTP server is not responding.

Are you using SSL to the SMTP server in Sonarr?

[Ashpool]

Yes SSL is enabled. This server only accepts SSL connections
Thanks

[markus101]

I wonder if it’s a TLS vs SSL issue:

E-mail Notifications Broken

These settings work in NzbDrone to send email through Gmail’s SMTP server: Server: smtp.gmail.com Port: 587 SSL: checked Username: Your Gmail address Password: Your Gmail password Send From Address: Your Gmail address Send To Address: Your recipient address The only difference from most guides online is using port 587 instead of 465. The difference appears to be security protocol related: 465: SMTP with SSL/TLS 587: SMTP with STARTTLS

587 works, but 465 doesn’t, but in Sonarr (and .net) it’s referred to as SSL, not TLS.

Are you connecting to a public SMTP server or your own?

@Ashpool

I wonder mono could be at fault.

I wouldn’t rule it out, easiest way test would be testing the connection from Sonarr running on Windows.

[Ashpool]

Gmail’s SMTP server on 587 works successfully. My ISP’s SMTP server uses 465

Good fix, thanks @markus101