3rd Attempt Also a Fail: My Experience Enabling iTunes Match 2-2018

My 4th Attempt Was the Charm!!!

(Posting here as a "technical solution" or at least a conclusion, to the original post where iTunes Match failed.)

I may be a glutton for punishment, but I really wanted to get my music library into the cloud for use with my new HomePod, so decided three days ago I would bite the bullet and give in if I had to by: Re-running iTunes Match; then adapt my "perfect" metadata back to align more with what Apple has in their library, and attempt to update my playlists to deal with all the idiosyncrasies I've encountered before when trying iTunes Match ...sort of a reverse match. On February 9, I purchased iTunes Match again and began the process once more. The net result: My latest iTunes Match of 26,045 tracks has been complete and active for more than 2 days across my iTunes for Mac, iPad Pro, iPhone X, Apple Watch, Apple TV and HomePod ... and it's PERFECT with almost no complaints. I'm both surprised and pleased, but still also extremely paranoid given my previous painful experiences. Following are additional details for those interested.

Environment

Same as before: My (macOS-based) iTunes library has 26K+ tracks: approximately 20% purchased from iTunes, with nearly all the rest having been ripped from my personal CD collection into ALAC (Apple Lossless). I've used iTunes since it's inception and have spent years carefully curating the library: Album Art is consistent and physically imbedded in the file as part of each and every track; Album Artists (and track Artists) are consistent across my entire library; Genres are consistent; 100% of my tracks have Star Ratings and I've begun additionally using the "Love" tag. I have nearly 100 (mostly Smart) Playlists, primarily oriented towards combinations of Artists, Genre and Star Ratings for use on my Apple playback devices and extracting tracks for further manipulation onto a dedicated USB SSD in my car.

Enabling iTunes Match

To hedge my bets if I needed to back-out of iTunes Match, I:

1. Backed-up the common and music parts of my rather massive iTunes Library (9TB of which 450GB is Music)

2. Deleted all formerly sync'd music and playlists from both my iPad and iPhone

3. I then purchased and turned-on iTunes Match via my Mac and let the process begin

Whereas the initial matching process on my 3rd attempt completed in around 12 hours just 9 days ago, this time using the exact same library, at around the 10-11 hour mark the matching process ended with no error messages, but thousands of tracks marked "Removed". As puzzling as that was since I had both cleared the cloud library at the end of my previous 3rd attempt (or at least I thought I had), and my service had been "Cancelled" several days before, I rapidly sorted and selected all the "Removed" tracks, then selected "Add to iCloud Music Library" to start the upload process. It took nearly 12 additional hours for those tracks to eventually upload and the matching process to truly complete. To my surprise, the result was terrific: I had the same number of tracks, albums, genre, and album artists as I had started with. Ratings and Love were still there. Track, Album and Artists metadata did not appear to have been changed -- AT ALL. "Ineligible" and "Duplicate" tracks appeared to be reasonable and as expected. I manually ran "Update iCloud Music Library" a couple more times, and no changes took place.

Next, I took a deep breath and enabled iTunes Music Library on my iPad and iPhone. The Apple servers must have been swamped, but after a period of time, my playlists populated. I had no new spurious iOS-only playlists as I had in my 3rd attempt the week before. I proceeded to begin downloading the playlist tracks I was interested in on both devices, and went in to check my master iTunes library... Each time I tried iTunes Match before, within an hour after completing the initial match or certainly soon after enabling it on any of my iOS devices, metadata problems began to creep into my master iTunes library ...but not this time.

What IS Different in the Present Result

It does not impact track or metadata content, or any track playback, but this time enabling iTunes Match, of the 26K+ tracks in my library, more than 21K show as "Matched" and 4K as "Uploaded". Only 3 tracks show as "Purchased" and those are the ones I purchased via iTunes since enabling iTunes Match a couple days ago... (There are actually thousands of purchased tracks.) IOW, on my latest attempt, iTunes does not show as many uploaded and purchased-designated tracks via iCloud Status as has in the past ...and matched items appear over-inflated depending on one's interpretation of that -- while all the tracks I should have remain available everywhere, and things seem to be operating just fine.

Perhaps someone else can explain why I have this difference now. It's puzzling to me why iTunes Match this time has changed it's mind in these three iCloud status categories, but I'm not going to dwell on it or try to change something, as long as things operate as well as the seem to be.

It Just Works

I can't tell you how many times in the past 2 days I've checked various counts in my iTunes library and on my iOS devices to see if "the cloud" has made some unexpected changes. It always has in the past, but there are still no odd changes to my library other than the iCloud Status differences I mentioned above. I've tried all the things I can think of that may trigger problems I've had in the past, but nothing unexpected has happened -- it's just all working and I'm sorry to come across so pessimistic, but I can't believe it. I've waited more than 24 hours. I've tried shutting down/starting up iTunes and my Mac multiple times, rebooting my iOS devices, changing ratings and love tags via iTunes and iOS, changing album name, album artist, artist names, and genre on one or more tracks. I've added a new playlist and changed it's name on both iTunes and iOS. In each case, the data has updated and become available to other devices within moments, and nothing negative has (yet) happened to my carefully curated iTunes Library as has happened so many times before.

Summary

Things can always change as we put our data up into the cloud and rely on someone/something else to be part of it's management. I get that. But, right now, I have a picture postcard version of iTunes Match operating across all my devices, including my new HomePod that can play any of my 26K tracks or playlists with a verbal command -- and as importantly for me -- MY album art and metadata is in-tact the way I have always had it for all of my purchased physical and electronically-downloaded music.

I wish I could say with certainty what I have done to make this work so others could benefit from the precise steps I've gone through. I've documented everything I can in these posts to perhaps assist, but I can only guess that something beneficial happened with my more recently using iTunes Match, turning it off for a few days, having it "Cancelled" and then re-enabling and going back through the process, or Apple has made system changes up in the cloud improving with iTunes Match. IDK. Perhaps someone here has a theory?

If iTunes Match all of a sudden goes nuts on me in the next few days, I'll be sure to update this thread. Good luck to all. When iTunes Match works, it really is awesome! It's pretty terrific being able to access all of my (purchased) music library from all of my devices, including via voice on HomePod.

I spent only perhaps an hour looking for anomalies and trying to figure out if I could live with it or develop workarounds, so with 26K tracks, my observations wont be real scientific. 😉 My impression is though, nothing was blatantly an error, e.g. no tracks were discarded, but a lot of what was changed simply wasn’t done in proper Album context (match is at a track level). The problem gets exacerbated when match for whatever reason only matches and changes some tagging on only a few tracks in a single album. It wouldn’t be as apparent for people that maybe buy only specific tracks, and don’t have the old LP or CD POV. E.g. having a different album artist name for only some tracks in most albums isn’t generally “right” if we were tagging by hand, or having album titles for different tracks that really are part of the same thing isn’t “right“ either, if you care about sort order or ever want to access all the tracks with a single sort of keyword via automated playlist, search, or Siri voice command. Sure, if all we use is playlists, I suppose one could build even more sophisticated and generic rules to attempt to capture the correct variations, but IMHO that just isn’t practical in most use cases, for most people. As the matching process eventually finalized in my trial, I would have had hundreds or thousands of situations where being able to play my music by genre, album (title), or artist name would have provided incomplete results using most may access method from what my original track tagging is without iTunes Match.

FWIW: I too have used iTunes since the month it first became available for Windows back in the day... then migrated the library to Mac a number of years ago. A couple times over the years I have spent untold hours across many months checking and rebuilding single album art for each track, ensuring album naming is consistent (esp Theatre and Performing Arts), and fixing Album Artist and how multiple Artist names are represented throughout my library. It’s benefited me greatly now being able to have a few handfuls of playlists, than I can put on random, and enjoy similar music wherever I may be, while still being able to get to everything by a single artist or to listen to a whole album in sequence. If you’ve done the same sort of curation, and have a relatively large library of various genre, I caution you from attempting enablement of iTunes Match unless you have the time and like to experiment. Just be sure you have a complete backup before you begin. Good luck.

Hey Jeff!

I've not noticed any slow-down whatsoever with any sort of add/change/deletions of music, playlists or other media within my library. I am running iTunes for Mac on a quad core 4.0GHz iMac -- but it appears iTunes does not make use of any more than a single core at one time anyway. While Match was underway doing it's uploads of my library (likely doing thousands of ALAC->256AAC conversions for upload), there were times when iTunes became unresponsive and podcasts I had playing would occasionally stutter, but once all that was complete, I've not had an issue playing, changing or modifying playlists, etc., etc. since.

FWIW, after 3-days of near bliss with my new iTunes Match environment, I've given up trying to break what I've got and moved my 1TB of pre-Match music backup files to an external drive just-in-case. Next up for me is to try and completely stop checking if something has mysteriously changed.

As crazy as it may be, I made a 4th attempt at iTunes Match with (so-far) stellar results. Check out this post for the detail.