iTunes won't sync most purchased songs

[tirerim]

I've run into a problem between iTunes and my iPhone 4S that I'm hoping someone else has seen or can understand. When I attempt to sync music, most of my purchased songs are not transferred to the phone -- instead, just their titles seem to be transferred, and if I try to play them on my phone, they get downloaded from iCloud or something. Which is great, except that I don't always have cell service, and I have plenty of space on my phone, so I would like to actually transfer the files.

It's inconsistent -- some of them get transferred, but others do not, even from the same album. In the "On My Device" section in iTunes, the ones that aren't transferred show as greyed out, with a small dotted circle next to them. Note that I do not have iTunes Match, but it seems like some sort of broken feature related to that. This is currently happening with iTunes 12.1 and iOS 8.3, but it's been going on for at least the past few versions of both.

I've tried turning off music syncing and then turning it on again to force everything to resync; I've tried manually managing music and dragging the ones that didn't copy to the device. So far, nothing works

 

[Pharmscott]

Are the purchases actually downloaded to your computer? Are the purchases from iTunes or another source?

 

[tirerim]

Are the purchases actually downloaded to your computer? Are the purchases from iTunes or another source?

All downloaded to my computer, and playable there; all from iTunes (Purchased AAC).

 

[tirerim]

I should note that regular AAC and MP3 files (ripped from CD or purchased elsewhere) all work fine; the only files it has problems with are those purchased through iTunes. I suppose it would be possible to strip the identifying information out of the purchased files in order to make iTunes think they were just ordinary AAC files, but that a) seems a little silly, and b) might make it think I hadn't downloaded them, and result in duplicates.

 

[gnasher729]

I've never encountered that problem. Maybe this happens if you select "Entire Music Library" under "Music" in iTunes. In that case try switching to "Selected Playlists" and make a playlist for your entire library.

 

[tinapanpan]

You can try this: plug your phone into your computer, click on the iPhone icon (top right) choose music from the list along the top of this page. check the box sync entire library. This will ask you if you want to remove and sync your entire library to your i phone. say yes to this. takes a little while but i finally got my entire library on the phone.

 

[mgroot]

COuld the files you're trying to play be old ones that still have DRM in them (from another apple id?) That's the only thing I can think off right now

 

[balamw]

Syncus interruptus.

I've been battling these grey circled tracks on my wife's phone for some time now. Apparently it means that they started syncing at one point and are in the library database, but the files aren't there. Then, it rejects any future attempts to overwrite the files.

My travails are in this recent thread. https://forums.macrumors.com/threads/completely-wipe-music-from-iphone.1886123/#post-21363612