Redirect data from Main Website to Email Server

Question

I have recently taken over SysAdmin duties for a SMB. They have an Exchange 2007 server in-house. Their website is hosted off-site. When trying to figure out a configuration error, I noticed that auto-discovery was not working remotely. DNS is through GoDaddy. WWW points to hosted server for website. _autodiscover, mail and the like are pointed to in-house Exchange server. All mail flows correctly. When doing an Outlook Test E-Mail AutoConfiguration, it fails. Unable to find https://domainname.com/Autodiscover/Autodiscover.xml for user abc. Is there a way to copy the Autodiscover directory to the hosted server path and have that work?

Answer 1

Oh no, don't do that.

You don't need to anyway. Outlook tries to find the autodiscover at both of these URLS in turn:

https://contoso.com/autodiscover/autodiscover.xml

and

https://autodiscover.contoso.com/autodiscover/autodiscover.xml

So providing the second one works all will be well.

Answer 2

You should now either disable port 443 on your public web server (unlikely..), or change the A record for "domain.com" to your Exchange box public IP. This is because the first url outlook tries is https://domain.com/autodiscover/autodiscover.xml

Next:

4. Add an A record for "autodiscover.domain.com" to your Exchange box public IP.

5. Obtain and install an SSL certifcate for CN or SAN for autodiscover.domain.com.

6. Ensure https://autodiscover.domain.com/autodiscover/autodiscover.xml shows some xml after logging in, and pressing F5 shows a new time stamp each time you refresh the page.

7. Check the URLs for autodiscover using these Exchange Shall commandlets:- Get-OABVirtualDirectory Get-ClientAccessServer Get-WebServicesVirtualDirectory Get-PowerShellVirtualDirectory Get-ECPVirtualDirectory Get-OWAVirtualDirectory Get-ActiveSyncVirtualDirectory Get-AutodiscoverVirtualDirectory