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It's probably related to the last import of the songs you've done. You'll probably find that it's only happening when you move songs to another computer or same computer and during the move it does not succeed in properly identifying the gaps between songs properly.
While I'm interested in more intelligent method of fixing this, here is what I've done to fix this.
NOTE: this will erase all your ratings. It does not delete the playlists or any other media.
1. Create a temp folder outside of the music folder, such as in the Documents or Downloads folder (same computer)
2. Move everything that is under the Music folder (in iTunes Music) to this temporary folder.
3. When done, go to iTunes and delete everything under Music in your library.
4. Click on File, Add to Library, and select that temporary folder.
5. Once it's done, test the songs, and they should play fully and properly.
At this point you might want to redefine the gapless play, if you like.
You should go and delete all the music from the temp folder you created earlier, as you don't need a backup copy of it at this point.
If you find a more intelligent way of doing this without having to delete and reimport all the songs, please let me know.1 vote by Dmitri Ivanenko
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