One Song Not Syncing To iPod

The song that won't sync is probably unchecked. You can check/uncheck all displayed songs using ctrl-click on a checkbox, or if you want to find it then you can use some smart playlists. Create a smart playlist with the rule *Playlist is Music* and the option *Match only checked tracks* and call this playlist Checked. Now create a smart playlist matching all the rules *Playlist is Music* and *Playlist is not Checked* (if necessary clear the option to match checked tracks) and call this playlist Unchecked. All unchecked tracks will be here.

If that doesn't solve things then the other possibility that comes to mind is that you've created two library entries for the same physical file. In this case only one file is placed on the device during syncing. One way to narrow down the search for these entries is to hold down the shift key and then select *File... Display Exact Duplicates*. iTunes will display files with matching details, one pair of which could be the culprit. For each pair examine the Get Info. Summary tab to see if both have the same location. If so, delete one entry while not letting iTunes delete the underlying file so the other can remain connected.

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