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Outlook 2016 for MAC throws SSL incorrect host name error

Posted on 2016-10-11
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Last Modified: 2016-10-11
Hi experts, I'm using Exchange 2013 for my server. From outside the network, users get a prompt that shows my web server IP address along with the incorrect host name. That address is actually from my website that is hosted by a 3rd party. May I know how can I correct this to show the correct SSL certs? Windows client can get the correct cert but not MAC client.
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Question by:totallypatrick
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Expert Comment

by:-MAS
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Hi,
You have to configure the URLs and split dns. Then configure autodiscover URL.
Please check these to configure your Exchange URLs and autodiscover.
http://www.mustbegeek.com/configure-external-and-internal-url-in-exchange-2013/
https://www.experts-exchange.com/articles/13676/Out-Of-office-not-working.html
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Expert Comment

by:Jason Crawford
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Check for a wildcard DNS record.  Better yet try an nslookup for random subdomains of your domain.  Something like:

nslookup -q=a test.yourdomain.com

or

nslookup -q=a grizzlyadamshadabeard.yourdomain.com

If they return an IP chances are you have a wildcard DNS record that you should remove.  The issue is Outlook will query autodiscover.yourdomain.com upon startup, and just like the examples above DNS will return whatever the wildcard record is pointing at, most likely your webhost.
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by:Ivan
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Hi,

did you configure Outlook Anywhere, and what names did you enter in Outlook when configuring it?
Where is autodiscover record pointing?

Regards,
Ivan.
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Author Comment

by:totallypatrick
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Hi all, I have a wildcard cert with autodiscover.domain.com in it. This issue only happens to Outlook 2016 MAC client. PC version works perfectly fine. Apparently PC and MAC version works differently. Refer to link 2. Exact error I encountered in link 1.

https://support.microsoft.com/en-sg/kb/3066652  
https://technet.microsoft.com/en-us/library/jj984202(v=office.14).aspx

My website domain.com is pointing to another IP address. How do I make "domain.com/autodiscover" point to my Exchange server? Is this the way to do it? I'm not sure.
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Author Comment

by:totallypatrick
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Doing a nslookup -q=a test.yourdomain.com returns the IP address of my Exchange server which is correct. However on MAC,  Outlook 2016 shows the IP address of my web server (hosting my company website) which is totally out.
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Expert Comment

by:Ivan
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Hi,

if you have wildcard certificate for your domain, then you can simple install that cert on your domain.com website, and that will fix it.

When it comes to autodiscover, first thing that Outlook is going to connect is going to be domain.com, and not autodiscover.domain.com. That is why you have a problem.

As you said, PC Outlook works differently, so they don't have this problem, after profile has been configured.

Regards,
Ivan.
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Author Comment

by:totallypatrick
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Referring to the attached file, I think i'm stuck at point 2A and it throws the SSL host mismatch error. It doesn't seems to go to 2B which is autodiscover.xxx.com
Capture.JPG
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Author Comment

by:totallypatrick
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Hi Ivan, I'm not familiar with web hosting and I've got a 3rd party to host it for me. I can use the same exact cert I used in Exchange server? It doesn't matter if the IP for the website and Exchange server is different right?
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Accepted Solution

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Ivan earned 500 total points
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Hi,

if you have wildcard cert, which covers all possible names for your domain, then you can use it.
IP address does not matter, yes.

One thing, do you use SSL on that website? If you have it enabled, but you don't actually use it for anything, then you can also simple disable it. That way, when Outlook try to connects to domain.com website, it will see that SSL is disabled, and will automatically redirect to next address is process, which is autodiscover.domain.com.
That way, Outlook is still going to point to your Exchange, and nothing would have to be done.

Regards,
Ivan.
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Author Comment

by:totallypatrick
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Thank you Ivan. Let me give it a shot tom. I'll try to input the cert tom but disable SSL.
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Expert Comment

by:Ivan
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If you disable SSL, then you don't need cert. That is if/ if solution. No need to do both things.
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Author Comment

by:totallypatrick
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Just discovered something. A SSL cert has indeed been applied by my web hosting company. If I go to https://119.31.237.67 there is indeed a cert applied as you can see and the certificate name matches what my Outlook shows. What should I do?
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by:Ivan
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Your domain is parked at 3rd party hosting, which is using it's on certificate. I am not sure if you can enter your certificate on it. Do you have some cpanel or some access to it, so that you try import or to try to disable SSl...
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Author Comment

by:totallypatrick
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Yup i have access to Cpanel. I can try to disable SSL tom
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Author Comment

by:totallypatrick
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Hi Ivan, you're right. I don't have the ability to disable SSL on the 3rd party hosting but nevertheless thanks a lot for your explanation.
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Author Closing Comment

by:totallypatrick
Comment Utility
Right answer
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