Exchange Password Required for Mac notification

1) You have to open up iTunes on the computer

2) Go to your Library and and find the song you're looking for that isn't playing and that is greyed out on the phone.

3) Click on the 3 little dots next to the song and choose 'Show Album In Library' and this will take you to that album

4) Click on the 3 little dots next to the song and choose 'Delete From Library' or you can click on the 3 dots next to the album name and delete the album from your Library

5) Do a search for that album/song and then add them back to your Library/Playlist

6) FIXED!!!

I dealt with this for like a year with songs that were there in Apple Music but wouldn't play in my playlist anymore. Just deleting from your playlist and re-adding will NOT work. You have to delete from you Library. From what I've noticed is that when the artist adds a new song to the album they re-upload the entire album with the new songs on it. This creates a duplicate of the album in iTunes. So then they remove the old album (that your playlist was pointing to). This means the songs in your playlist are pointing to old metadata and not the actual song. Hope that helps!

See the post from ApexSpeed where they explained how to solve it-->https://discussions.apple.com/thread/250290897?answerId=250548118022#250548118022

Try deselecting every song, in iTunes & synch. This will remove every song from your phone. Then reselect the songs, and synch again. I think the Metadata was screwed up in the last update. I think that moving all songs from synch, reset it. At least it worked for me.

I fixed the issue for myself. I downloaded iOS12.3 to my computer, synced my phone (TWICE) and all the missing songs that were grayed out are now back to normal. For some reason sometimes the first sync doesn't work so I did it again (the second time only took a minute anyway). Glad I got things back to normal as I have a 3 week road trip in June. Hope that helps.

I booked a service call yesterday with Apple (amazing service) and a really helpful guy called Antonio from Portugal helped me out. Short answer is that there is no clear understanding of what has caused this to occur. I originally used only my own music synced via iTunes on Windows to my phone. Since switching on Apple Music and moving my library to the cloud, everything initially worked perfectly but something screwed up over the past 4-5 weeks which caused my iTunes account to 'forget' my personal library (items greyed out, clicking them gave me the 'not licensed for your region' error message) and only gave me the option to play music for what it knew about in the Cloud. The only solution was to disable iCloud music and recreate my entire library by adding my music folder back into iTunes, wait for it to import, re-sync to my phone and switch iCloud music back on. Took an absolute age (10k tracks) and I've now got to wait a few days to see if it all works (takes a while to re-sync to the Cloud). I'll report back if it doesnt work, but for now, if you are seeing this message and you've tried the other suggestions, the only other option is as I've described.

What worked for me was:

leave the music app open on phone before syncing

disconnect wifi on phone

sign out of itunes account on pc

i was also signed out of icloud

when i synced again all the songs that were greyed out before and said “not available in your region” were downloaded to my phone. If i look under songs the only songs that are greyed out now are purchased songs that i deleted from my pc or some purchased songs that i edited will have a second copy of the original song. If i connect to wifi and sign into my apple id all those greyed out songs will show a cloud download icon to let me download them or play them while connected to wifi.

I think I FINALLY FIXED IT!!!

If you notice the grayed out songs or darkened songs in dark mode on your iPhone's iTunes app,

1. Then, connect your iPhone to your computer
2. Go To iTunes on your computer
3. Go To your iPhone within iTunes browsing to it under "Devices", drilling down to "Music"
4. If you notice ALL of the songs that are grayed out in the iPhone's iTunes app just may have a "dotted circle" next to each one

Note, the song is there, you can view it's properties, it confirms the song is indeed on your iPhone

Note, the song is indeed on your computer as well, within iTunes, you can browse the hard drive and find the song functioning fine

There are 4 ways listed at this link what to do to fix the issue, however, within 30 minutes I found another way. For now, it is fixed. The link is here: https://techgearz.com/fix-dotted-circle-itunes/

I did try solutions 2,3, and 4 in the past, all failed. I refuse right now to do solution 1. That is to find EVERY song manually, delete it off your drive's folder, and drag'n drop back in or import back into iTunes library then resync. That solution requires to go to the properties of every file, locate it, then delete, re-add, resync.

My fix, I hope not a temporary work-around, is easy and fast.

1. Within iTunes on your computer, drill down to Devices, select your iPhone, and go to the song or Play List, find the song,
2. Right-click the song and select Add to Device, then select your iPhone.

Not only did the dotted circle go away on that song, but it went away on all my songs that were similar.

I hope this brings and end to this problem which occurs weekly, definitely every month.

I've been having this problem with music on my Mac that I added from my CD collection, not from iTunes purchases, this hit me after I had purchased a new iPhone last fall but hadn't updated to Catalina and couldn't manage my phone manually. I finally cleared / updated my incompatible software and updated to Catalina.

This problem went away in Catalina / iOS 13.3, after I did a couple of things, any of which might have made the difference:

1. On Mac, in Music>Preferences>Restrictions, I disabled Apple Music
2. On Mac in Music>Preferences?Advanced, I reset warnings
3. On Mac in Finder>iPhone>Music tab I could see the same Sync music settings I used before (selected artists, genres, and playlists), so I didn't change anything.
4. I synced my phone, which took quite some time (10-15 minutes) and finally the grayed out songs will play on my phone. The storage usage audio jumped for me as well.

I think some combination of disabling apple music (so it wouldn't try to find songs in the cloud) and letting a long sync complete got me to where I can play music from my CD's onto my phone again.

I had this same issue for a ton of new songs I'd just purchased on iTunes. I signed out of my account on my phone and when I signed back in it let me download all the music.

I randomly had this problem tonight with a few songs. I went into the Info for the songs in iTunes and all of them had composer info. I removed it and re-synced and they all work now.

iOS 13.1.2

Thanks for the help Lawrence. Since the issue only occurred after I synced my phone, hence my computer backup was already “faulty”, so I ended up deleting all my music off the phone and itunes, and added everything back in afterwards. It was a lengthy ordeal but it fixed the problem.

I had the EXACT same problem!

I updated to IOS 12 and my phone didn't recognize a portion of the music on my computer(not a Mac). So this is what I did, I deleted the Apple Music app on my phone and reinstalled it. And re-added the music, re-synced my phone to my computer. Added the music to my phone and BAM, the songs were back on my phone.

My Ipad mini did this too after a WiFi sync. Took the advice in previous replies to physically plug in my mini to the computer. Had to unlock it, and once my computer recognized the mini, I re-synced and all the greyed out songs returned to life. Thanks everyone. :)