Sony mp3 players before 2008 do NOT work with server 2008, same driver certification error. also SStage will not load the devices entry tab. Use javastage if device detected and delete your music library off the device and reload songs to be able to use songs, if you have the "test driver" mode on. This has been confirmed to work but very unstable and cannot convert mp3 tracks to OMG without using SStage 3.1 do not use 4.x series media devices tab is unacessessible.
I love Sony PMP's, all of them, but the SonicStage software is complete and utter garbage In my experience so i'm not surprised
it's a shame, because it's the only propper/legal/easy way to use ATRAC3 format too :'( but oh well WMA will do for me