I have this exact same issue (I have about 4500 songs on a Microsoft Zune), so it is not a Apple v. Microsoft issue. I think several of the respondents are right - simply too many songs to index. I have left it indexing just out of curiosity on long trips, and eventually it indexes the songs, but it can take an hour. I leave it plugged in, but it will still "de-sync" when the car is off, so I have decided to used an older Zune I had, delete everything, and only add in the podcasts and a few playlists I really like. I am hoping that does the trick. As an alternative, I also purchased a 3 foot long RCA male-to-male splitter cable from Amazon - it has a 3.5mm headphone plug on one end, and the RCA red and white plugs on the other. I leave the red and white plugs hooked into the AV inputs in the console, and plug the other end into the headphone plug and control the songs via the MP3 player, using the "A/V" input to the stereo. It works perfectly, and sound quality is much better than bluetooth (works for my phone, too).