Email Notification: TLS does not work

[taylorstan 1]

Hello,

 

I have not been able to send email notifications using TLS/SSL using the email notification plug-in. I am able to send using non-secure settings. I have attached the log of the tests I have done. I am in the process of migrating my server to FreeNAS 11. I was not able to send using secure setting on my previous Freenas 9 set-up. Any help would be appreciated.

 

Set-up

 

Emby: 3.5.2.0 (FreeNAS plugin build)

OS: FreeNAS-11.2-RC1

Plug-in Version: 3.1.2.0

embytlsemailerrorlog.txt

[Luke 39396]

Hi there, let's wait and re-evaluate once you are using an official build that has been packaged by us. Thanks.

[chrissi55 2]

Same here with Server 4.0.1.0 and SSL / TLS enabled via port 465

 

Log says

2019-02-02 13:04:29.734 Error App: Error sending email: System.Net.Mail.SmtpException: The operation has timed out.   at System.Net.Mail.SmtpClient.Send(MailMessage message)   at MediaBrowser.Plugins.SmtpNotifications.Notifier.SendNotificationCore(UserNotification request, CancellationToken cancellationToken) 

Switching over to non-SSL / non-TLS via port 25 -> no problem.

Mails were received properly

 

Mailprovider = own Domain with Let's Encrypt Cert (valid until end of 03/2019)

No Problems with SSL / TLS from other Apps / Web-Apps like Nextcloud e.g.

 

Mailserver is definitely reachable.

Edited February 2, 2019 by chrissi55

[Luke 39396]

It says timed out which means it is unable to connect. There is not much we will be able to do about that. I would double check the plugin configuration.

[chrissi55 2]

Yes ist says "unable to connect" ... but with same credentials and same server url but with port number 25 instead of 465 and no SSL instead of SSL / TLS it worked.

 

Now, same credentials, SSL / TLS Settings, URL and Port i use for nextcloud notifications, router (fritz!box) push notifications, my mobile devices for connecting my IMAP account 

all are working with SSL / TLS

 

Emby is calling "not connectable" - that is what i'm not able to figure out.

Edited February 2, 2019 by chrissi55

[Luke 39396]

 

 

Emby is calling "not connectable" - that is what i'm not able to figure out.

 

That's unrelated.

 

But regarding mail, the issue could be that the SSL certificate is being rejected. The server is shipping it's own certificate store and not using your local store on your server machine.

[rbjtech 4886]

Try SMTPS Port 587 .. 

 

465 is no longer the official SMTPS port - although the majority will still accept it as it's obviously got a lot of history .. 

Edited March 9, 2019 by rbjtech

[Luke 39396]

Ah great info, thanks !

[chrissi55 2]

Yes, worked for me.

 

587 with SSL/TLS connected to the server.

And, as you've written ... 465 is still in use out there in the WWW

Edited March 10, 2019 by chrissi55

[taylorstan 1]

I'm good now. got new setting from ISP.

[Luke 39396]

Thanks for the feedback !