What type of iPod and what firmware level do you have?
Have you read the notes for your device located in the little blue box? http://boards.synccommunity.com/n/do...d-493139bf3002
Most devices have extensive notes that discuss the limitations of that specific device and firmware level and, for example, what may happen if your device has a duplicate playlist on it.
The iPod Touch 2nd Gen at version 2.1.1
has the following notes listed:
In order to upgrade your iPod Touch to this firmware level, the latest version of iTunes is required.
In order to ensure that all digital media on your iPod is indexed, Album, Artist, Genre and Song metadata must be properly populated in iTunes and synchronized with the player before connecting the iPod to Sync. If you need assistance on updating your metadata, please view: http://docs.info.apple.com/article.h.../en/15347.html
When a Now Playing playlist is active on your iPod before connecting it to Sync, Sync will resume playing the Now Playing playlist on the iPod from where it left off and will begin to index the device in the background.
Sync will display AUTOPLAY UNAVAILABLE if there is no active Now Playing playlist on the iPod when it is connected to Sync.
When turning your vehicle on and off, the Now Playing playlist on your iPod Touch plays by default and may not match the last playlist you selected using Sync.
When attempting to play a playlist on the iPod, the Sync screen may display BAD MEDIA. This may mean that the music that the playlist contains is not compatible with Sync (this may be due to copy protection) or that the playlist is empty. If you are able to play the media that is contained in the playlist by playing it through another method, such as disconnecting the iPod from Sync and successfully playing the music through the headphones, re-connect the device to Sync and attempt to play the media again. If media playback does not resume, you will need to perform a Master Reset of Sync and reconnect the device to Sync. Once you have performed a Master Reset, the information can be retrieved after you reconnect your iPod to Sync.
NOTE: Performing a Master Reset will completely erase all media files and phonebook and text messaging information, and the information will not be able to be retrieved. Any customization will not be saved and the Sync unit will return to the factory default settings. For complete instructions on performing a Master Reset, view page 34 of the glovebox manual at: http://www.nsapp.fordtechservice.dea.../08sycsu1e.pdf
When connecting your iPod to Sync or resuming play after you turn the vehicle back on, your iPod may not communicate properly with Sync. Resetting the iPod and making sure it is fully charged may allow the player to reconnect.
When playing the last song in a playlist or last chapter of an audio book in a playlist, pressing the radio SEEK RIGHT button will not take you back to the beginning of the playlist.
You may not be able to find and play your On-The-Go playlist using Sync with this iPod version.
When attempting to play an empty playlist on your iPod (such as On-The-Go,) Sync will display BAD MEDIA. You may then make another selection.
When playing albums with multiple artists, Sync may not play the tracks in numerical order.
If you are playing a song and select the same song for playback by using the voice commands or radio controls, the song may not start over. Pushing the SEEK LEFT button once may take you back to the beginning of the track, but you may have to press the SEEK LEFT button a few times quickly, or make another selection.
There are times when the track counter on the display may freeze, yet audio may still continue to play. If the track timer does not recover after twenty seconds of playback, wait until the next song is queued for playback or select another playback option such as pressing the SEEK RIGHT or SEEK LEFT buttons.
When using voice commands with this device, you may hear: "Speech control not available with this device." If this happens, there may be a duplicate playlist on your device. To correct this, remove the duplicate playlist using iTunes, resynchronize iTunes with your device, and reconnect the device to Sync.