Apple Music library won't sync between computer and iPhone

[DualShock]

I have an iTunes library in Windows that I had originally synced to my iPhone via USB. I then started an Apple Music subscription and up to today, just streamed some music by searching or using Siri.

Today I turned on iCloud Music Library in iTunes, and it ran through the process of matching my music and uploading the matches that were not found. This appears to have worked successfully.

Now on my iPhone I turned on Sync Library, which took a couple of seconds, and also appears to have worked successfully.

However, now when I add albums or songs from Apple Music through either iTunes or my iPhone, the updates don't appear in the other location. I'm baffled as to why this is happening.

I checked the Apple Music support pages and they indicate to sign in with the same Apple ID on both devices. I have 2 Apple ID's, my main iCloud one, and another that I had previously been using to buy songs on iTunes (I will call this one the "iTunes" Apple ID.). I have signed in using the main iCloud one on my phone, which I use for all iCloud services, and also the iTunes one on my phone for music purchases. (In the iCloud settings page on my phone, the one at the top of Settings with my name in it, the iTunes Apple ID appears under "Media & Purchases".) I also used my iTunes Apple ID when I originally signed up for Apple Music through my iPhone. This same iTunes Apple ID is signed into iTunes on my computer.

Given all that, does anybody have any ideas as to why albums I add on iTunes on my computer and on my iPhone do not show up on the other device? Thanks!

 

[Terbor]

Using iOS14? I think this is connected to that update. I logged out of iCloud and did a reset on my iPhone. Now the only music and playlists that I have are purchased (not subscription) on that device despite being logged in again. I noticed that anything I do in iTunes on my iMac syncs to the Web Player (https://music.apple.com/) but not to my phone. I created a new playlist and it appears on the web. The reason I suspect iOS14 is that my iPad is also not syncing with the new playlist.

 

[DualShock]

Using iOS14? I think this is connected to that update. I logged out of iCloud and did a reset on my iPhone. Now the only music and playlists that I have are purchased (not subscription) on that device despite being logged in again. I noticed that anything I do in iTunes on my iMac syncs to the Web Player (https://music.apple.com/) but not to my phone. I created a new playlist and it appears on the web. The reason I suspect iOS14 is that my iPad is also not syncing with the new playlist.

Interesting. Yes I'm using iOS 14. I deleted all the sync'd iTunes music from my phone and re-enabled cloud sync in iTunes and my phone, and I'm also only seeing my purchased music showing up on the phone. I also tried to add an album in Apple Music to my library in iTunes, and it indeed showed up on the web player.

Very strange. I'm actually on the phone right now with Apple Music support so we'll see if they have any other info.

 

[Terbor]

Or it could be a timing issue? There was some sort of issue with Apple Music and some of their other services yesterday morning and into the afternoon. Last night, my phone and iPad both managed to sync. They both show the new playlist that I created and also my phone seems to have all the songs in the library (although it has not downloaded everything).

 

[DualShock]

OK so here's how it all went down. I got it working with the help of Apple's support over the phone, took about an hour and a half with screen sharing on my phone and computer. I did encounter the minor services outage when initially running the sync but everything was appearing and syncing in the web player so we ruled out the iTunes side of it.

Turns out that it appeared to be my having 2 Apple ID's (one for iCloud, the other for iTunes / App Store) that was causing the issue. The sync surprisingly worked perfectly fine on my retired iPhone 5S on iOS 12 that is now effectively an iPod Touch.

To resolve the issue, I logged out of my 2 Apple ID's on my current phone and logged back in with both. Then the sync started working properly.

Unfortunately we only discovered this after I did a Reset All Settings and a Reset Network Settings as recommended by the Apple support person. This caused its own issues because every setting was reset for every app (notifications, Apple Pay, etc.), so I then restored from a backup from that morning. This caused me to lose a couple of important iMessages because I did not have iCloud messages turned on (again, due to having a different Apple ID set up for iMessage). I promptly switched the iMessage e-mail to be the same as iCloud so that I could take advantage of iCloud messages. ?