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Autodiscover & email configuration issues for 1 new PC

Can someone tell me what I'm doing wrong?

SBS 2011 standard running exchange - 10 users have been set up for years - laptops at home, on the LAN and at a remote location connected by VPN
Their website is at a web hosting company.

Added a win 10 PC with Office 2016 at the remote location.

when opening outlook for that user's account, he'd get prompted for his password, and warnings about the certificate is  doesn't have the correct name, etc.

Running the microsoft remote connectivity analyzer for autodiscover it says:  Connectivity Test Successful with Warnings

under that it says: The Microsoft Connectivity Analyzer is attempting to test Autodiscover for markg@domain.com.
       Autodiscover was tested successfully.

Looking at things, it keeps trying to get to https://domain.com which resolves to the web server, not SBS box.  Can I just drop the autodiscover.xml from the SBS box onto the web server in a new autodiscover directory that doesn't currently exist?

Where should autodiscover.xml be located?  on the SBS box? on the web page?

There doesn't seem to be an autodiscover entry in the DNS zone.

I added an A record and pointed it to the sbs server.

pinging autodiscover.domain.com resolves to the SBS box.

But the Microsoft analyzer seems to have the web server IP cached?

This has been working for existing users.  Does Office 2016 and Exchange 2010 on SBS 2011 not play nice?
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Avatar of Cliff Galiher
Cliff Galiher
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You should post the full set of results.

But if Outlook tells you that you don't have the correct names in your SSL cert - you probably don't have the correct names in your SSL cert (based on how Exchange is configured). Just because autodiscover is in DNS doesn't mean it's in the SSL cert.
Outlook 2016 uses autodiscover to connect to exchange. If certificate does not have a autodiscover entry and a host A record it will fail to connect giving cert error.