Mac 2016 Outlook v15.9 certificate problem

18 Macs on 10.12.4 and Mac Mail still has the same issue.  Setup mail.domain.com as the mail server and it complains that www.domain.com doesn't match mail.domain.com.

This happens because it's looking up "domain.com" and in our case *.domain.com points to the server holding www.domain.com.

Not everyone will have this configuration and it's a major F Up on Apples end.

I still don't think it's an issue with Apple...  I only say that because I've configured Mac Mail (v10.3) to use my exchange information and I haven't gotten any certificate messages *at all*.

Also, if it was an Apple issue, don't you think that we would have seen an issue with the certificates when Apple released an update and not Microsoft? Outlook is now on 15.33 and I'm still experiencing the issue. It just doesn't make sense at all.

This is not a Microsoft issue.  It's an Apple issue.  Microsoft is forced to use the internal connection procedure that Apple has built into their OS.  If Microsoft had any say in this then Outlook would connect via OWA.  But they don't and it doesn't.  Want proof?  Try to setup an Exchange account in Mac Mail.  Same exact issue.  Apple in their infinite wisdom has thrown Autodiscover out the window.  Therefore the apps are attempting to lookup *.domain.com.  In my case if you attempt to connect to *.domain.com you'll get my web server instead of my mail server.  So any time I try to setup an email account in Outlook for Mac it tells me WEB doesn't match MAIL.  Well, no crap!  That's why the only fix for this is to either fudge the certificate or just ignore the mismatch and tell it to trust it (both solutions outside of MS's control).

Which leads me here.  For the first time I have a user that bought the student version of Office so now I'm stuck with Mac Mail and this fix doesn't work.  Mac Mail refuses to connect even if you trust the bogus cert.  That has nothing to do with this forum but I figured I would chime in because people here were all over the place with this issue.  Now I'm off to try and find a solution for Mac Mail....you suck Apple!

the only thing that I have done is check the box to "Always trust...." at the top of the error message.  I'm frankly not sure if this is advisable but it is the only way I can get past this error from coming up every time I start O/L.

Hi John,

Just want to clear have you added www.domain.com or just domain.com the certificate?

I have added domain.com but it's still not working for me.