Postfix issues

[Aiwa]

I've been Googling for hours now and can't seem to find anything close to a solution for the problem I'm having...

So, I've got my server setup with Postfix / Dovecot. Postfix is set up to auth SASL via Dovecot...

Whenever I try Outlook, or Thunderbird, from my PC, I can authenticate to both POP3 and/or IMAP, but Outlook refuses to send a test e-mail through postfix's SMTP...

Send test e-mail message: Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

So I tried to set up everything on my gmail account the same way and it works... Gmail's web client can successfully auth with both POP3 and SMTP. I'm able to both send and receive e-mails for my e-mail user@mydomain.com through the Gmail client...

So, that leads me to believe that everything WORKS... So, why would Gmail work, but not Outlook?

I've got less +F running on the maillog and both Gmail and Outlook generate the exact same logs and both return a client out: OK. Meaning successful authentication... So if outlook is successfully authenticating, why can't it send an e-mail?

Here's the log

Apr 19 23:55:15 vps2 dovecot: auth: Debug: auth client connected (pid=2231)
Apr 19 23:55:15 vps2 dovecot: auth: Debug: client in: AUTH#0111#011PLAIN#011service=imap#011lip=x.x.x.x#011rip=x.x.x.x#011lport=143#011rport=64892#011resp=<hidden>
Apr 19 23:55:15 vps2 dovecot: auth: Debug: pam(user,x.x.x.x): lookup service=dovecot
Apr 19 23:55:15 vps2 dovecot: auth: Debug: pam(user,x.x.x.x): #1/1 style=1 msg=Password:
Apr 19 23:55:15 vps2 dovecot: auth: Debug: client out: OK#0111#011user=user
Apr 19 23:55:15 vps2 dovecot: auth: Debug: master in: REQUEST#0111268383745#0112231#0111#011887de6223011605d6c44c94ef1b167bd
Apr 19 23:55:15 vps2 dovecot: auth: Debug: passwd(user,x.x.x.x): lookup
Apr 19 23:55:15 vps2 dovecot: auth: Debug: master out: USER#0111268383745#011user#011system_groups_user=user#011uid=500#011gid=500#011home=/home/user
Apr 19 23:55:15 vps2 dovecot: imap-login: Login: user=<kacx9c>, method=PLAIN, rip=x.x.x.x, lip=x.x.x.x, mpid=2232
Apr 19 23:55:15 vps2 dovecot: imap(kacx9c): Disconnected: Disconnected in IDLE bytes=11/299

[Aiwa]

Interesting... I changed the port to 587, opened the firewall obviously, and now I get this from outlook.

Send test e-mail message: None of the authentication methods supported by this client are supported by your server.

And, this..

Send test e-mail message: Establishing an encrypted connection to your outgoing (SMTP) server failed. If this problem continues, contact your server administrator or Internet service provider (ISP).

I'm guessing that means I need to set up SSL or TLS.... Right?

[Rhett]

Your isp may be blocking port 25, it's pretty common actually, 587 works fine in those cases.

On the auth methods, you would need to check and see what you have setup on the server vs the methods you are using etc... we can only guess really.

[Aiwa]

Indeed my ISP was blocking port 25 and it appears outlook requires starttls, so I went ahead and set up certs for postfix and dovecot.

All is up and running on 587 & 993/995 with self-signed SSL certs.

Thanks Rhett

[Aiwa]

And it gets better. Google enforces strict SSL and won't accept self-signed certificates. :sad:

Time to go find a reasonably priced SSL cert from a CA.

[Aiwa]

How about StartCom? They're free (class 1).

Ya, I got one from them a bit ago. Just have to set it up.