Well, i’m not sure what is happening. Last time i used Openfire on Windows Server was with 2008 R2. Though, in this video How To: Video on setting up SSO/AD with Openfire @speedy is installing what it seems on 2012 R2 and it works ok for him. If Openfire logs don’t give a clue, maybe Event Log will show something. Something might interfere with Openfire web server, so it times out. These servers are regular setups, no additional services/software?