(See Previous Post for back story). One of the issues that we ran into after the Exchange migration, was that the Outlook clients on the old small business domain would not connect to Exchange on our main domain. New Outlook (2013+) could connect using ActiveSync during the testing, but older Outlook clients can only have one Exchange profile at a time.
Outlook was prompting for credentials of the user’s login with SBS server domain, causing Outlook to crash. There were a series of things that I tried including redirecting Autodiscover on the SBS Exchange to our main one, but I think the one that finally worked was to remove the Autodiscover virtual directory from the On-Premise SBS Exchange completely.
Elevated Exchange Management Prompt to see current settings:
Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, ExternalUrl, Identity
Next, remove the Directory for that Identity returned:
Remove-AutodiscoverVirtualDirectory –Identity “identity”
In my case it was this:
Remove-AutodiscoverVirtualDirectory –Identity “SBS11\Autodiscover (Default Web Site)”
Answer ‘y’ for Yes
This should allow you successfully connect Outlook running on a different domain using “manual setup”
You also will likely need to go into “More Settings” on the bottom of the first screen and fill out information for “Connect to Microsoft Exchange using HTTP” and Exchange Proxy Settings.