When Outlook loses connection, or when using Outlook Anywhere you'll probably see the following dialog box:
Of course you could select the "Don't ask me about this website again" box, but that's only a local override. What you can do, is suppress the window completely by making a registry edit. You'll have to navigate to the HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook\AutoDiscover\RedirectServers key and add your server names as REG_SZ (String Value) leaving the data field empty. You can add as many servers as needed.