Sending Mail from External Client

Virtualmin
1

Hello all, I am having an little issue with a fresh install of Virtualmin. Everything locally works without error however only sending from Outlook does not, I am able to receive without fail and even sending locally works fine.

mail.log shows no errors just timeout on authentication and my client states “None of the authentication methods supported by this client are supported by your server.”

I am trying to make this server a bit more secure than my last so SSL is enabled. I do have my certs installed.

Postfix main.cf
smtpd_tls_cert_file = /etc/postfix/postfix.cert.pem
smtpd_tls_key_file = /etc/postfix/postfix.key.pem
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

Dovecot 10-ssl.conf
ssl_cert = </dovecot.cert.pem
ssl_key = </dovecot.key.pem

I think I am missing something simple, I have made no modifications to either configuration since install other than the certificates. Client side I have tried all types of encryption. None, SSL/TLS. STARTTLS, and even Auto

Any advice on this issue would be helpful.

Thank You

2

What’s in the maillog/mail.log when you try to authenticate?

This isn’t directly related to TLS (though some clients will refuse to send PLAIN passwords over a non-TLS link, and that’s the default auth mech, since it allows using the same password for all services). But, if SSL/TLS is working, clients shouldn’t complain.

3

Hey Joe thanks for the reply. This is a section from my log during authentication.

Oct 12 22:32:20 external dovecot: imap-login: Login: user=, method=PLAIN, rip=24.96.***.***, lip=74.208.***.***, mpid=54643, TLS, session= Oct 12 22:32:26 external dovecot: imap-login: Login: user=, method=PLAIN, rip=24.96.***.***, lip=74.208.***.***, mpid=54645, TLS, session= Oct 12 22:32:45 external postfix/smtpd[54638]: warning: hostname user-24-96-REMOVED does not resolve to address 24.96.***.***: Name or service not known Oct 12 22:32:45 external postfix/smtpd[54638]: connect from unknown[24.96.***.***] Oct 12 22:32:46 external postfix/smtpd[54638]: lost connection after EHLO from unknown[24.96.***.***] Oct 12 22:32:46 external postfix/smtpd[54638]: disconnect from unknown[24.96.***.***] ehlo=1 commands=1 Oct 12 22:33:01 external dovecot: imap(test.DOMAIN): Logged out in=466 out=8311

As you can see not real errors authentication just seems to not have an authentication path yet all ports are listening.

4

It doesn’t look like your client is even trying to authenticate. It’s seemingly working for IMAP, the SMTP connection isn’t. I dunno what to do with that. Maybe try another client, like Thunderbird, and see if it behaves differently or the same. That might give us a clue.

5

Hey Joe thanks for your help. I am sorry but had to get the server up for a client so I went ahead and re-imaged it and have it all setup now. Did not make any changes on the client side. I think there was some small setting which was blocking the auth communication. I suppose we will never know, thank.