I had Autodiscover working for months but recently it just stopped. I’m not sure why, but it may be related to removing the last Exchange 2003 servers from service recently. Maybe some setting got wiped from AD when I uninstalled Exchange 2003 (as per the procedure Microsoft gives). Basically what was happening was that the email address field was being autopopulated by the user’s UPN rather than their email address. Since we have a single label domain, the UPN isn’t a valid email address, and autodiscovery fails.
Anyway, I ran Get-AutodiscoverVirtualDirectory and it looks like the autodiscover URL isn’t set. Pretty sure I set this at some point.
[PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory -server exch2010fe1 | fl InternalUrl,ExternalUrl InternalUrl : ExternalUrl : [PS] C:\Windows\system32>
I just piped this to Set-AutodiscoverVirtualDirectory to correct the problem:
[PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory -server exch2010fe1 | Set-AutodiscoverVirtualDirectory -ExternalUrl 'https://webmail.example.com/Autodiscover/Autodiscover.xml' -InternalUrl 'https://webmail.example.com/Autodiscover/Autodiscover.xml' [PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory -server exch2010fe1 | fl InternalUrl,ExternalUrl InternalUrl : https://webmail.example.com/Autodiscover/Autodiscover.xml ExternalUrl : https://webmail.example.com/Autodiscover/Autodiscover.xml [PS] C:\Windows\system32>
After resetting the InternalURL and ExternalURL, autodiscover works again (we have SRV records that tell Outlook to look at webmail.example.com for the Autodiscover service).