Your automatic reply settings cannot be displayed because the server is currently unavailable. Or Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again later. Do you get either of these error messages when trying to use Automatic Replies in Office 2007 or 2010?
The reason this error message is displaying is because Outlook can’t see your Client Access Server due to proxy restrictions. To get this to work you need to add a bypass to your proxy server for your CAS. To do this you need the name of your CAS.
To get your Client Access Server name you need to log into Outlook Web Access (OWA) and click on the question mark icon next to Options. Then click on About.
A pop-up window will appear containing a whole host of information about the server. We are only interested in the line entitled “Exchange Client Access server name” find this, copy the name to the clipboard for use later.
Open up your Internet Options settings in Control Panel and click on the “Connections” tab, make sure that the “Bypass proxy server for local addresses” is ticked then click on “Advanced”. In the “Exceptions” panel type in your CAS server name followed by .* then press OK->OK -> OK to close all of the windows.
Open up Outlook. Click on File -> Automatic Replies and it should works now as per the screenshot below.
EDIT: If the above steps don’t resolve your issue you could try rebuilding your Virtual Directories, or check your authentication and SSL settings in IIS on each Virtual Directory on your CAS servers. See if this helps and let me know. Default settings are here: http://technet.microsoft.com/en-us/library/gg247612.aspx
Can you improve on any of the tips I’ve discussed here? If you can let me know in the comments.