When setting up the automatic reply and out of office from your Outlook 2010 having Exchange 2010 you might have the problem with a pop-up saying “Your automatic reply settings cannot be displayed because the server is unavailable”.

I have managed to solve this with a DNS record in your infrastructure. Create the following SRV record to fix the issue.

Service: _autodiscover
Protocol: _tcp
Port Number: 443
Host: myexchangeserver.mydomain.local

On the client PC run the following to refresh the DNS. Make sure you run the CMD as Administrator

ipconfig /flushdns
ipconfig /registerdns

This should fix the problem and the user will be prompted to enter his Out of office settings.