I have never been able to get my iPod Shuffle to work with Media Center even after upgrading to the lates release.
The steps I follow are:
1) redetect devices
2) plug shuffle in usb port
3) device recognition dialog appears
4) Hit OK
5) Option dialog appears
6) Hit OK
7) Dialog asks to initialize and erase ipod
Answer yes
9) Nothing happens
10) Unplug and plug in again
11) Flash 'Drop Files Here' appears in lower left for 5 seconds and disappears
12) Click on Hand-helds and am told that none are attached
iPod works fine with iTunes. iTunes is not running during all of the above
Media Center Registered 11.1.118 -- C:\Program Files\J River\Media Center 11\
Microsoft Windows XP Workstation 5.1 Service Pack 1 (Build 2600)
AMD Athlon 1989 MHz MMX / Memory: Total - 523 MB, Free - 209 MB
Internet Explorer: 6.0.2800.1106 / ComCtl32.dll: 5.82.2800 / Shlwapi.dll: 6.0.2800 / Shell32.dll: 6.0.2800 / wnaspi32.dll: N/A
Ripping / Drive D: PLEXTOR CD-R PREMIUM Mode:Normal Type:Auto Speed:Max
Drive F: Mode:Normal Type:Auto Speed:Max
Digital playback: Yes / Use YADB: Yes / Get cover art: No / Calc replay gain: Yes / Copy volume: 32767
Eject after ripping: Yes / Play sound after ripping: No
Burning / Drive D: PLEXTOR CD-R PREMIUM Addr: 0:0:0 Speed:52 MaxSpeed:52 BurnProof:Yes
Drive F: PLEXTOR DVDR PX-708A Addr: 0:1:0 Speed:40 MaxSpeed:40 BurnProof:Yes
Test mode: No / Eject after writing: Yes / Direct decoding: Yes / Write CD-Text: Yes
Use playback settings: No /