SMTP with TLS worries

tulekparson

SInce upgrading to Version 1.18 the SMTP Settings aren't working anymore...

Unable to connect via TLS

The certificate-chain on my mailserver is working and no expired certificate is in the way.

Here's the log from my mailserver:

Jun 15 10:27:33 mail2 imaps[32398]: login: [127.0.0.1] no.reply@xxx.xxx plaintext+TLS User logged in SESSIONID=<mail2.xxx.xxx-32398-1686817653-1-4
Jun 15 10:27:34 mail2 postfix/submission/smtpd[7075]: connect from unknown[XX.XX.XX.XX]
Jun 15 10:27:34 mail2 postfix/submission/smtpd[7075]: SSL_accept error from unknown[XX.XX.XX.XX]: 0
Jun 15 10:27:34 mail2 postfix/submission/smtpd[7075]: warning: TLS library problem: 7075:error:14094410:SSL routines:ssl3_read_bytes:sslv3 alert handshake failure:s3_pkt.c:1493:SSL alert number 40:
Jun 15 10:27:34 mail2 postfix/submission/smtpd[7075]: lost connection after STARTTLS from unknown[XX.XX.XX.XX]
Jun 15 10:27:34 mail2 postfix/submission/smtpd[7075]: disconnect from unknown[XX.XX.XX.XX]

Anyone got an idea, what OSTicket is trying there and how to remedy this?

KevinTheJedi

tulekparson

You are getting SSL/TLS failures. Please look at your server logs to see why.

Cheers.

tulekparson

KevinTheJedi

That I saw ;-) The Problem is, that only OSTicket seems to have issues, I have 100+ Clients and around 80 Users plus some Webservices using my mail server (and SMTP with TLS) with zero issues.

I checked the certificates and made sure that postfix is indeed using them. If any other client would complain and fail the handshake I might see the mail server at fault. For the server running OSTicket it's a freshly updated Debian Bookworm installation. So in which log should I poke around?

KevinTheJedi

tulekparson

Maybe try one of these?

Also, double check and make sure the hostname is indeed correct.

Cheers.