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Convert Mojave-age iTunes.itl library on external drive to Monterey Music .musiclibrary

Having some issues converting a Mojave .itl to .musiclibrary on Monterey.


As with many users on this forum, I have a large legacy iTunes library I keep on an external drive for space. The legacy library dated back to 2010, but I successfully upgraded it via my 2019 MacBook running Mojave to the .itl database file. (My latest .itl file was created Oct 2021 and updated June 2022). All working great. Side note: I do not use music streaming services, and never will, so have been watching the OSX sea change with trepidation.


Fast-forward to now. I finally made the jump directly to Monterey on my MacBook (I had been running Mojave a bit longer for some 32 bit app support). Didn't even think about the iTunes to Music app issues, since Mojave was running Music app via the .itl database file just fine. I'm realizing that not having my iTunes databases on my local machine meant that the .itl never got converted the new format during my Monterey update.


Shouldn't be an issue, right? I should be able to simply OPTION+click Music and point Music app to my external drive .itl file and have it do its business. But, when I do this, Music app sits around doing apparently nothing, with a "loading" wheel. I've left it for hours, no luck. Overnight, no luck. As other users have seen via Activity Monitor, Music.app seems to be doing nothing but idling. No information is getting gleaned from the old .itl file.


I've read all the various ways folks have migrated their libraries on these boards, have done most of these, and nothing is working. Thinking this was a Music app file permissions / external drive thing, I've granted Music app full disk access (Systems Preferences --> Security & Privacy --> Full Disk Access). Tried again, nada. Maybe the conversion really wants the strict Music app directory structure - I made a copy of the iTunes folder on the same external drive and arranged the directories according to what Music app wants to see (see thread Old iTunes folder to Catalina or Big Sur … - Apple Community). No luck. I'm steps away from restoring my MacBook from my last Mojave Time Machine backup, and moving through a step-wise upgrade to Monterey... but that really, *really* shouldn't be necessary. I *might* have access to a Big Sur machine tomorrow to attempt a Mojave .itl --> Big Sur .musiclibrary conversion. But that also seems excessive. Where do I go from here?


Apologies for posting an issue similar to some older ones, but my Music app behavior seems a bit distinct.

MacBook Pro 15″, macOS 12.5

Posted on Aug 16, 2022 10:37 AM

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Question marked as Top-ranking reply

Posted on Aug 24, 2022 5:24 AM

Hi there!


I spent a week variously playing different tracks, or deleting the album artwork cache to see if I could force Music to load embedded artworks. No love there. The embedded art always appeared at the top play bar thumbnail, but never in the main browser / viewer.


I finally decided that the key might be having the media (with their embedded art) available during the initial .itl --> .musiclibrary conversion that I did on a work machine running Big Sur. I cleared off a travel-friendly large capacity external drive and copied my entire legacy iTunes media library, including all music files, to that. Then I took that in to the Big Sur machine to re-make the library fresh from the iTunes one.


This was key! Having the media files present when you option+click Music to load the .itl library meant that at library conversion, Music (slowly) loaded all embedded artwork present in the music files. This took some significant time. Every single track of mine has manually-embedded artwork ... so I wasn't missing a single album cover. I suspect that some users might see patchiness in the return of album artwork if they had tracks lacking properly embedded images.


Once Music finished loading all artworks, I made sure to copy the artwork cache it built back to my external drive to transfer to my own machine. (~/Library/Containers/ ... /Data/Documents). This included the artwork folder and the SQL files associated with it. Loaded the new .musiclibrary file onto my home external drive, dropped the artwork cache in its home in ~/Library, opened the library .. and voila! Completely re-built library including artworks.


My last question regarding Music app: will adding album covers via Get Info --> Artwork still embed album art in the track? Or will this just put a .jpg in the artwork cache and no longer properly embed to the file?


Thanks for your input!


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Question marked as Top-ranking reply

Aug 24, 2022 5:24 AM in response to turingtest2

Hi there!


I spent a week variously playing different tracks, or deleting the album artwork cache to see if I could force Music to load embedded artworks. No love there. The embedded art always appeared at the top play bar thumbnail, but never in the main browser / viewer.


I finally decided that the key might be having the media (with their embedded art) available during the initial .itl --> .musiclibrary conversion that I did on a work machine running Big Sur. I cleared off a travel-friendly large capacity external drive and copied my entire legacy iTunes media library, including all music files, to that. Then I took that in to the Big Sur machine to re-make the library fresh from the iTunes one.


This was key! Having the media files present when you option+click Music to load the .itl library meant that at library conversion, Music (slowly) loaded all embedded artwork present in the music files. This took some significant time. Every single track of mine has manually-embedded artwork ... so I wasn't missing a single album cover. I suspect that some users might see patchiness in the return of album artwork if they had tracks lacking properly embedded images.


Once Music finished loading all artworks, I made sure to copy the artwork cache it built back to my external drive to transfer to my own machine. (~/Library/Containers/ ... /Data/Documents). This included the artwork folder and the SQL files associated with it. Loaded the new .musiclibrary file onto my home external drive, dropped the artwork cache in its home in ~/Library, opened the library .. and voila! Completely re-built library including artworks.


My last question regarding Music app: will adding album covers via Get Info --> Artwork still embed album art in the track? Or will this just put a .jpg in the artwork cache and no longer properly embed to the file?


Thanks for your input!


Aug 17, 2022 1:45 PM in response to gilyan

Hi folks,


I successfully got my iTunes library read into Monterey Music following the suggestion by JRN on this thread:

https://discussions.apple.com/thread/254093986


Briefly: I have access to a machine running Big Sur at work. I brought my .itl over on a thumb drive, and directed the Music app on that machine to open the .itl database via OPTION+ click. Music on Big Sur was able to bring in my database (minus album art) but maintaining key data like play counts. I then transferred the Big Sur created .musiclibrary database back to my external drive, transferred the music files to the appropriate /Music/Media/Music file structure, and voila.


Any suggestions on replacing the lost album art? iTunes file structure for storing Id3 tag art is a bit opaque, so I'm not sure how to troubleshoot this.

Aug 17, 2022 2:00 PM in response to turingtest2

Thank you! Any clue which iTunes files Music will point to when extracting the album art?


I suspect that since I only had Music convert the .itl file (since it's not my machine), it was missing access to those cached artworks. Perhaps the solution would have been to bring my external drive in and point Big Sur to the whole shebang.


So I suppose I'm asking - think there's any way to point Music to those now (after creation of the new .musiclibrary db) for extraction?

Aug 17, 2022 2:03 PM in response to gilyan

Music creates an artwork cache at ~/Library/Containers/com.apple.APMArtworkAgent/Data/Documents.

iTunes created it at <Library Folder>/Album Artwork.


When Music converts an iTunes Library.itl file I don't think it pays any attention to the old Album Artwork folder. As tracks are processed in the new library embedded art should be added to the cache, or Music will attempt to look for corresponding art in the iTunes Store. It seems sometimes this process stalls and a lot of artwork might be temporarily missing in a newly converted library. It should sort itself out over time, particularly if there is embedded artwork to process. Failing that deleting the cache will force it to be reevaluated.


tt2

Aug 17, 2022 2:17 PM in response to gilyan

Removing that cache doesn't seem to force Music to do anything, as far as I can tell. I removed:

~/Library/Containers/com.apple.APMArtworkAgent/Data/Documents

from the directory. Closed and restarted Music. No love. Also closed Music, swapped libraries, then closed and swapped back. Not sure what process beyond opening the app would force the embedded art scraping...



Convert Mojave-age iTunes.itl library on external drive to Monterey Music .musiclibrary

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