@ehj-52n said in Mail-Notifications not working:
Secure Connection: [X]
In that case, it isn't (shouldn't) be port 587 - but port 465.
If you have access to the mail server, you should have port 587 which start 'in clear', and after a STARTTLS is issued from the client, the connections switches over to TLS (SSL).
Port 465 is like 587 (called submission), asks for authentication etc but everything from bit 0 will by TLS encrypted.
This is a classic 'gmail' setup :
[image: 1636382726081-24ce6ecf-a0c2-4bf9-ae37-8fe6f7b2712d-image.png]
(but, be careful, it might be possible that gmail won't accept connection from an 'unknown' device - mail client like 'pfsense'. See your gmail / Google security settings)
You could even consider abbandning port 587 usage, because you control your won devcies, right ? Make them use port 465 (SSL only) and stop having port 587 being used = open to the internet. It's just 'one risk less' to handle.
Delivering mails from a client to a mail server is all 'port 465' these days. Nothings goes (shouldn't) out in the open any more.
Very comparable to what happened to 'http' : it's game over. It's https now.
: be careful with this one.
The certificate the (your !) mail server is using should be recognized as valid, like a Letsenscrypt certificate. A self signed cert will fail.
I'm using Letenscrypt certs for my Debian + postfix mail server, works great.