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  1. Starting with iTunes 11 without any reason Apple removed gapless playback check box under track Options. Apple claimed that iTunes would now automatically determine if the album needs gapless playback which judging from numerous posts never worked reliably if at all. Allegedly albums that were previously marked for gapless playback in earlier versions of iTunes would continue to work. I upgraded to iTunes 12 a couple of days ago and it appears that now gapless playback is completely broken. I tried to experiment. I imported one of my CDs on older iMac with iTunes 10.7 and OS X 10.6 and I marked it as gapless. I then copied imported AAC files to my retina MacBook with iTunes 12 and gapless playback no longer works. I poked around trying to figure out how iTunes determines if the album is gapless and it appears it is getting this information from iTunes Music Library.xml file located under iTunes folder in user's home folder. If a track is a part of gapless album, there is a string that marks the track as part of gapless album: <key>Part Of Gapless Album</key><true/> Correct me if I am wrong, but the gapless flag must be contained within AAC tag and iTunes 12 appears to be parsing the tag and adding this information to iTunes Music Library.xml file, but it doesn't seem to pay any attention to it during playback. I synced freshly imported gapless album to my old 5th gen iPod and on the iPod the album plays perfectly. I am not sure if it's bug in iTunes or Apple decided to abandon gapless playback completely, but it would be very unfortunate. It's a very useful feature and it's a shame that Apple decided to just arbitrarily remove it from iTunes. P.S. I placed a call to AppleCare and they told me that gapless playback was removed from iTunes 12 completely and suggested using product feedback page at http://www.apple.com/feedback/ to request to put the feature back into iTunes. Perhaps if enough of us do it we'll get gapless playback back. In the meantime, stick with iTunes 10.7 if you can. It was the last version of iTunes that supported it.