Purchased song shows in App Store history, but NOT showing in iTunes Store for download
I purchased a holiday song back in 2010. It is still in my iphone and working fine. When I go to the App Store app and look at my purchase history, the song is there. However, it was on the list of songs in the Apple Music app on my Macbook, but when I tried to download I got an error. I have no idea how it is somehow not downloaded when I have been listening to this song on my computer and iphone for years without issue.
I tried various "fixes" I found in the community. I logged in and out of the Music app. I restarted the app and opened it using the left Shift key so that it wouldn't go back to the last view I used in the Music app. I checked my wifi connection and tried to download the song several times. At one point, it kept asking me to sign in/Buy every time I clicked download and nothing happened no matter how many times I signed in, and yes, I was already signed back into my account in the Music app. Finally, I restarted my computer, which has by the way been restarted recently when I updated my software.
After signing back in to Apple including signing in on the Music app, I can no longer see the song on my list of music in the Music app. It is still on my iPhone without issue. If I can't see it in purchases in the iTunes Store, then how can I re-download it?
If it makes a difference, I did have a subscription to Apple Music for a time, but canceled about a year ago. I purchased this song in 2010 before Apple Music was a thing, so it was not part of a playlist that I made just in a subscription status. I've also listened to the song since I canceled the Apple Music subscription.
Also, I used to download purchased music and it would automatically show up on all of my devices, including my kids' devices since we're all in a family group. It doesn't do that anymore. I also noticed today, when trying to troubleshoot this issue, that when I go to System Settings on my Macbook, click on my Apple ID, click on iCloud, the Music app is no longer on the list of apps that can be synced via iCloud. On my iPhone when I do the same, it shows Music as an option and it is turned on. Seeing that there are these differences is really confusing.
To be honest, I haven't kept up on how features have changed for a long while because mostly the updates haven't affected my use for the most part, so I have no idea how long it has been since Music was removed from this as an option. While I'm generally a savvy computer user, but not someone who spends a lot of time exploring features, I have felt that Music has been unduly complicated an annoying ever since the changes that accompanied the update from iTunes to Music. Everything used to be so easy and intuitive and now I have to Google instructional apps for things that used to be so simple and some stuff can't be done anymore without 3rd party apps.
I do have a subscription to iCloud storage as well and specifically purchased it so that I could ensure that everything, including music, photos, and tons of files that I have zero time to sift through are saved even if my Macbook crashes. I have no idea if there are differences with paid storage vs. free storage.
If anyone can help me figure out how to download this song that is hanging out there in purgatory, actually there are two of them it seems, I would appreciate it. If someone could help me understand why things seem so different on iPhone and Macbook these days, I'd appreciate it. I feel like things on the phone are still pretty easy to do and work well, but there used to be more features on the Macbook and it was easier to do things there, then save things to the phone. I don't get it.
Oh, one last detail, this song I'm trying to get was because I wanted to update my holiday playlist. I can see the playlist on my Macbook and it used to be on my phone. I never removed it from my phone and haven't changed any settings for music downloads or playlists or the like in ages, but the playlist is just missing there. My grand plan was to re-download the missing song, update my playlist with some stuff I got recently, then figure out how to get it onto my phone. It seems I can no longer wirelessly update Music like I used to do. I could connect the phone and do it, but frankly haven't seen my cord in ages since I got a magnetic charger.
Reading back over this, I sound sort of hopelessly out of touch. I swear, I'm not as bad as this sounds, but two hours into what I thought would be a quick fix so that I could listen to my holiday songs via a bluetooth speaker rather than on the crappy Macbook speakers and I'm super frustrated. Any help and shoulder pats appreciated!
MacBook Pro 16″, macOS 14.5