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.