Are you experiencing these problems with a Clip+ or a Clip Sport?
For the Clip Sport, I am aware this device has the following limitations.
-> Will not play wma files with digital rights management (drm)
-> The Music database will not recognize more than 2000 audio files
Also, make sure all your music audio files (and subfolders) are placed inside the main Music folder.
How are you attempting to play your music in your car, with an audio connecting cable?
Or are you attempting playback via micro USB cable? (Just a wild guess.)
