SSL/TLS Question

Discussion forum for Enterprise Edition.
Post Reply
Posts: 17
Joined: Tue Mar 05, 2013 7:12 pm

SSL/TLS Question

Post by frontdist » Sun Sep 22, 2013 1:54 pm


I am attempting to set our mail clients up with the correct settings in Outlook and am running into a roadblock with it working correctly (as per my understanding of how it should work anyways).

In Outlook, getting IMAP set up over a secure connection worked fine over port 993 with "SSL" selected as the encryption option, however it will not work if set to "TLS"

For SMTP in outlook, I was unable to get it to work over port 587 with "SSL" selected, I had to use port 465 and set SSL as mandatory in the mailenable SMTP settings. My Mac with Apple Mail was able to connect over 587 just fine, but I had to force SSL on 465 (rather than have it optional like on 587) for it to work. Setting it to not have SSL mandatory on 465 resulted in a SMTP test failure in outlook.

Note: the reason I cannot force SSL on 587 is that it is our MANDATORY submission port, we are unable to use port 25 as it is intercepted by our SonicWall email appliance and gets blocked as a submission port.

In either case, for both IMAP and SMTP, I am unable to select "TLS" as an option in outlook, the test fails every time. Based on the documentation that I have read, should I not be able to use TLS or SSL with mailenable?

Post Reply