Can't work out mail.app and remote sending

[Steve3]

Hi all,

I'm evaluating zimbra for the small business I work at, and have a test server up and running. We're mostly a Mac shop, and if we go to Zimbra, it will be necessary to provide sending from various remote IP addresses- laptops at home, trips, ect.

I can't get SMTP authentication worked out between Zimbra and Mail.app. From home I can telnet to port 465 on the zimbra server, so there's no IP blocking or firewalls stopping things. I've tried various combinations of the Outgoing Mail Server authentication settings in Mail.app, and of zimbra's "enable authentication" and "TLS authentication only" options, and haven't found the right one.

I have this same concept in place on my existing mail server, I just can't replicate it here. Could someone help me figure out what I'm doing wrong? Surely this has been solved before, but I failed to find the answer.

Thanks,
Steve.

[jholder]

Are you getting a bounce, or you just can't seem to connect?

A TLS Auth issue will return a bad password or something.
If you get through, do you get a bounce?

Also, take a look at /opt/zimbra/log/audit.log and see if you're even connecting.

jh

[Steve3]

Nope, no bounce. The message never gets accepted. Here's what I'm doing:

From OS X Mail.app, compose a message to an external account- gmail or .mac. Send it from my zimbra.domain.com account.

Briefly after send, I get a "can't verify SSL Certificate" dialog from Mail.app. Sure- it's a self signed cert, this isn't surprising. So we know the client is talking to the mail server if the certificate is being handed back.

Mail spins it's wheels for a bit, before timing out and reporting "Cannot send message using the server zimbra.domain.com", with the pop up menu and invitation to choose a different mail server.

Tailling audit.log, I see many reports of the format
[imapSSL-Server] [my remote ip] security - cmd=Auth; account=; protocol = imap;
With some protocol=soap, as I have a web client open also.
Never do I see an SMTP connection logged in audit.log or or mailbox.log.

[Steve3]

OK, I managed to solve one problem and reveal another. I had a bad setting under configurations: Server: Trusted MTA Network. I had 127.0.0.1/8 instead of 127.0.0.0/8. Making this change explained why the moderately high mailling list I subscribed this address to hadn't been getting any mail, as I'd broken the local mailer.

But now, when I try the same send from an external address, I promptly get a "relay access denied". In my current mail server, this is addressed via "pop authenticated relaying", where an IP address that makes a successful POP connection is whitelisted for sending for 15 minutes.

I don't understand where the parallel concept in zimbra is.

Thanks,
Steve.

[Steve3]

In case someone else tries to answer this question, I got Mail.app to send from external hosts by setting it to send on port 465, using SSL, Password authentication with a username of my full email address, and the paired password.