Mac Mini 2011 i7 16 GB Ram 256 SSD and 2 TB Second Hard Drive running Sierra 10.2.3 - iTunes 184.108.40.206 Every time I open iTunes Match it is determining gapless playback on what I assume is the same 500 songs each time, at least till I add more songs. This problem is not unique to iTunes Match. I had the same problem a year ago with another iTunes library ( Not using iTunes Match ) that stopped tagging songs as being checked for Gapless playback. Nothing that I tried would correct the problem and the number increased in proportion each time I added songs. I eventually gave up and started all over with a new library and had to re-import thousands of songs and recreate all my playlists. I would truly like to avoid this with my iTunes Match library as I have an enormous amount of time invested in getting it configured the way that I want. It seems to me that there should be a way to repair the library or simply turn off Gapless Playback. I have all the songs stored locally as well as in the cloud and I maintain double backups of the media files. I do not see how I can start over without downloading 30,000 songs again from the cloud into a new library and recreating all my playlists. It is not much of a problem right now as it only takes seconds to run through 500 songs each time I start iTunes and otherwise the library functions fine. However as I continue to add more songs to the library the time will increase to the point of becoming a real problem. Thank You for for any response, hopefully someone will be able to suggest a simpler solution. Even more important I would like to figure out what I am doing to cause this problem. My library consists of multiple sources, Over 400 of my own CD's ripped to MP3 320. Songs purchased through iTunes, Amazon etc. and some old out of print music downloaded from various other sources. All of a sudden it just decides to stop keeping track of the songs it checks and keeps rechecking every time I open iTunes. Additional Info: I have the same iTunes Match library running in Windows 7 on another PC that is updating just fine with any additions and changes that I make on the Mac and does not exhibit the same Gapless Playback problem on startup.