There is this great little app called Always On Top that does exactly what it says, basically you can run or designate a "window" on top of all other windows using the command Ctr-Alt-T
Apart from that it just sits in the background doing nothing....... (lol probably a CIA monitoring app....I hope its doing nothing but these days who knows).
Anyway like I said I love it and its one of the first apps I install when setting up a new pc.
Long story short I found in Server 2008 it stopped working, it would run no problems eg in the ProgramFiles (X86) folder but hitting Ctr-Alt-T didn't cause windows to stay on top.
The solution and although obvious I'm posting it here for SEO reasons in case anyone else gets caught out is to simply right mouse click the exe file then click on Compatibility tab then check the "Run this program in compatibility mode for - Windows Server 2003" check box and hit apply.
The restart the app......sweet all good again :)