Here is another blog written selfishly, because I always forget where I put the entries that need to be added to the web.config files, in the offending pipeline, when needing to troubleshoot an RMS issue.
If you are having problems with RMS, and your standard IRMCheck, and DebugView checks are bearing no fruit, on a WS2008 server (usually for tough group expansion issues), you can open the web.config files in the c:\intetpub\wwwroot\_wmcs\certification and c:\inetpub\wwwroot\_wmcs\licensing directories, and add these couple of lines right after the </DRMS> *closing* tag, fire up DebugView, then go to a command prompt and issue an 'IISReset' command.
Go ahead and repro your problem, and you should get a lovely log (assuming the problem is on the server, and not a client issue), of all of the junk RMS is doing behind the scenes. All of the functions being called, and the return values as well as any error messages.
<add name="TMS Trace" value="4" />
*Warning*: Always make a back-up of your web.config files *before* you do any modification. If you don't...then you can save your tears for the Friday night 'chick flicks' on Oxygen television (I used up all mine when Tom Brady (from the New England Patriots) got injured a few weeks ago). You've been warned.