Very helpful information.

Sent from my iPad

On Jan 28, 2015, at 11:34 AM, Michael B. Smith 
<[email protected]<mailto:[email protected]>> wrote:

Autodiscover is a surprisingly complex little protocol.

You never get a certificate or warning error, because with Office 365, you 
never connect to the provided domain name.

When Outlook (or a mobile client) attempts to connect to 
autodiscover.example.com<http://autodiscover.example.com> over SSL, they can't. 
The connection is denied.  This tells the autodiscover protocol that it needs 
to redirect its request to a different host. It gets the different hostname by 
connecting to autodiscover.example.com<http://autodiscover.example.com> 
directly over port 80 (no credentials - just a custom request that says "tell 
me who to connect to"). Autodiscover then connects to that site - which must be 
an SSL site and have a valid SSL certificate.

The above is very simplified. If you want the TL;DR details, see:

http://msdn.microsoft.com/en-us/library/ee332364(v=exchg.140).aspx

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Matthew Topper
Sent: Wednesday, January 28, 2015 8:00 AM
To: [email protected]<mailto:[email protected]>
Subject: [Exchange] Office365 and Autodiscover

I'm wondering if someone on this list can help with a question I have on 
Office365:

Why isn't there a certificate error when I point the autodiscover CNAME to 
autodiscover.outlook.com<http://autodiscover.outlook.com>?

I think I'm missing something with how Office365 works, since I know I run into 
problems under normal circumstances when 
'autodiscover.example.com<http://autodiscover.example.com>' isn't in the 
certificate on the Exchange server, but how can Office 365 handle that?

Matthew Topper

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