Before I begin I'll say that I restored all my music from Crashplan backups. What was lost was my iTunes metadata and all stats I've generally considered myself over the years very adept at moving and organizing my iTunes library from one computer to the next, as well as keeping all files nestled neatly in the iTunes Music folder. How I went from being comfortable with managing my music to losing a majority of my music I still am not totally sure. A Random Cleanup on a Random Day I keep all my music consolidated on my NAS because I like to have everything kept in one place. I have iTunes make a copy of any new music into this music folder because why not, I trust it. With the new iTunes I realize that the File menu has a Library sub-menu for "Organize Library", foolishly I use the "Reorganize files into iTunes Music" option. I would figure that iTunes would update it's file paths for all files so that any syncing doesn't cause any problems. Perhaps it doesn't, I don't know. But I do know that I used this option and on the next sync, **** was gone. Music Disappears The iPod Classic (80GB) that I keep in my car rarely leaves to get synced, but after certain periods of time I will bring it inside to sync it based on how much new music I have added. I haven't added much in the past 6 months but regardless I wanted to sync my iTunes library and update stats and playlists and what not. I plug it in, it syncs, and is done in about 3 minutes. Way too fast. I look and now see the iPod only has 20Gb used, where as my Library is about 70GB and typically all fits on the iPod. I look over my Library and everything looks fine, 70GB of music are still in my Library. But as I go to play my music something strange happens, the file I just double-clicked disappears and then iTunes starts playing some other random song. I do this a few more times and more stuff disappears. I now realize that somethings wrong and go look in the music folder in the Finder. The music folder is now down to about 20GB of music. Everything's gone. Restore from Backup Crashplan is pretty damn awesome but it's also pretty damn slow to restore 70GB of music! I don't blame Crashplan or my internet speed for this, it simply is what it is. After restoring (4 days later) I just put my music folder back together and aim iTunes at the restored library and after a long iTunes Match/Genius updating the same thing happens! All music is more or less gone! Now I start to wonder if some weird iTunes Match problem is occurring. I kind of like iTunes Match. I'm sort of weary of iTunes Match. I kind of don't like dealing with iTunes Match. I won't use iTunes Match anymore. I can't say for certain but I sort of feel that after my first restore that once I opened iTunes again "Match" did something to my library or downloaded changes that caused the same weird deletion to occur. I think this because this time I wasn't using my iPod Classic to do a sync and yet my music disappeared (mind you I used a restore from a month ago just to be sure I wasn't restoring a messed up library). I restored twice from Crashplan and did complete swaps of my music files and the same thing kept happening once iTunes Match finished doing it's initial updates, which BTW took forever for it to do. So possibly in it's hour long update, it was systematically deleting music locally that possibly wasn't "matching" with the database of music that it had cataloged in iCloud. This doesn't seem to make sense IMO because Match should just be uploading anything it doesn't recognize but I don't know. Starting Over At this point I had started doing local backups on my NAS again because I didn't want to deal with a third Crashplan restore. This time I decided I would cut my losses and just build a completely new iTunes Library. It was a sad day to realize that the, nearly, 8 years of music info was going to be lost. I would sometimes have a few late night beers and sort by "Date Added" and I could totally recall when and where (and from whom) I had borrowed CD's to rip, or when I borrowed an external HDD to copy a crapload of music to my library. It was a strange walk down memory lane, but over 8 years of music you can really trace your life steps based on how you imported your iTunes music. I know it sounds brutally sad, but try it, it's fairly intriguing. But now this is all gone. Now all "Date Added" is January 9, 2013. Now all "Play Counts" are 0. Now all "Ratings" are 0 stars. Call me Crazy If you've made it this far into this post then hopefully you've found this story interesting and not just some sad rant about some dude who lost his tunes. It's kind of strange having to start over with your iTunes collection, especially when you've taken a small bit of pride in having such a weathered and meticulously organized collection of digital music. Hopefully some of you out there have some advice, but hopefully something in this TL;DR post someone will avoid the crap that I've had to go through. Perhaps it will inspire a LOT of you out there to get Crashplan, for without that, all truly would have been lost.