can't send emails from Outlook

[gopher49]

I just configured the mail services for Zentyal.  The webmail works perfectly fine, however, when sending from Outlook I get a send error.  I'm able to receive.  I just can't send. I'm using SSL IMAP and TLS SMTP.  I have SMTP configured for outbound authenticatino required and no luck.  I even tried disabling outbould authentication for SMTP and stilll no luck.  I know port 25 is open for I'm able to receive inbound emails to the server.

Any suggestions?

[darke]

Try, SMTP — 465 and TLS, my help.

[Marcus]

Hello choerske@ProgressiveIPSol,

Maybe it is because of a bad username/password... When retrieving mail, my username is in a different format compared to my sending configuration.

e.g.
IMAP:
server: Zentyal public IP or Zentyal canonical name
username: username

SMTP:
server: Zentyal public IP or Zentyal canonical name
username: username@exemple.com

Best,

Marcus

[christian]

Marcus,

Regarding accounts, I think you're right on the principle but I would be surprised if it is not the opposite. I mean IMAP (as configured in Zentyal) requires "mail address" to be used for authentication.
On the other hand, SMTP, if requiring auth, should work with "user account"... not sure about the last one 

To me the issue is maybe more related to listening port: activating SSL, port 465 MUST be used while no SSL or TLS can use both 25 or 587, if I'm  not wrong.

[Marcus]

Hello christian,

I think that those differences comes from my email setup.  In my case, I'm using Zarafa for viewing my emails.

So, for fetching emails using IMAP with Zarafa, only the username is needed.  But, when sending an email, since I'm using Zentyal's default SMTP server, the full email is needed (otherwise I'm not able to send emails).

Still, you may be right on the ports.  On my side, only TLS is active on my SMTP.

Best,

Marcus

[gopher49]

First of all.  Thanks for the responses.  I really appreciate all of your help.  It ended up being that I had 'internal' checked on the Mail Service setting!  I think I did this on accident.  Once un-checked I was able to send via port 465 SMTP TLS.

Now,

How do I get SSL to work on the roundcube web mail service?  Only HTTP works.

[gopher49]

I now see the 'listen on SSL' on my webservers instance... I'm all good now.. I also changed the port to 444 so it wont interfere with my admin page.  I'm thinking of setting up a virtual host though for I want to void anyone being able to access my admin page from any IP address.