Issues getting SMTP Notifications working

tadl

Hi,

Apologies if I've not posted this to the correct area.

I've been trying to get SMTP Notifications working on 2.7.0.

I've installed ACME and successfully configured a wildcard cert and applied it.
I configured the cert with example.com *.example.com and *.homelab.example.com

When I test the SMTP settings I get the following error: Could not send the message to blah@example.com -- Error: Failed to connect to ssl://smtp.example.com:587 [SMTP: Failed to connect socket: fsockopen(): Unable to connect to ssl://smtp.example:587 (Unknown error) (code: -1, response: )]

I can successfully telnet to the mailserver on port 587 from the command line on the router.

Any helpful suggestions greatly appreciated.

Bob.Dig

@tadl You don't need a certificate to send those notifications in the first place.

stephenw10

You installed that cert on your own mail server?

tadl

@stephenw10 it’s been installed for the web GUI so far.

stephenw10

Ok so I assume you are using example.com only as an example? You have your own domain you're using?

You don't need a client cert to connect to smtp.

You are trying to connect to an smtp server at your domain. Is that not your server?

SteveITS

@tadl try unchecking the SSL option.

tadl

@stephenw10 correct, sorry for not making that clear.

I have my own domain, mail is via a third party mail server, & I’ve followed instructions for sending mail via SMTP by generating a token/app password for use with the sending/from address.

Gertjan

Compare

@tadl said in Issues getting SMTP Notifications working:

Error: Failed to connect to ssl://smtp.example.com:587

with

@tadl said in Issues getting SMTP Notifications working:

I can successfully telnet to the mailserver on port 587

The first is TLS (SSL) and the second uses non-SSL, which is correct : 587 is not encrypted at the start.
It can, after connection, if the START-TLS server capability is available, use TLS.
pfSense will issue a START-TLS if this is the case.

A pure, from the start, TLS connection can be used with smtp, server port 465.

tadl

@SteveITS I’ve tried the various SSL/TLS options with plain or login, but no luck.

tadl

@Gertjan Thank you.

The requirements are Port 587, Auth method is Plain, with STARTTLS

@SteveITS I've just tried it again, without Enable SMTP over SSL/TLS or Validate the SSL/TLS certificate presented by the server enabled, and it worked...

I thought I'd tried that earlier and it failed, not sure what I've tried now, been messing about with it for so long :)

But thanks everyone, all good now.