Q: Songs are greyed out with a dotted circle next to them and won't sync

So I have a 6S + 128, and ifunbox didn't work for me. I think mostly because I don't get my songs through itunes. I have... uh... other ways. Anyway, what I did was delete all the offending songs from itunes. Then I put them back on one album at a time, syncing to my phone with each sync. I think originally I tried to load several hundred at once and for some reason that caused problems. When I took it slow and steady, I had no more dotted circles. (I'm still in the process of doing it, but all spot checks are passing and I've already put on a bunch of songs that failed to load before.)

How to make your music available at all times:

Here is a workaround for the above issue of Apple removing your music from your phone without asking, forcing you to redownload the music you own. All of your music will be available offline.

I am using OSX 10.11.1 and iTunes 12.3.2.35.  I am not using Apple Music, iTunes Match or any such nonsense.

I am not a techie or a pro, just a guy who wants to be in charge of his data.

Use your good judgment if you do this.

It is a bit long but Apple is no longer in control of my music!

WARNING: You will be resetting your phone which erases all data -- be wise and do what you must to backup/protect your data.

1. Back up any files you need outside of iTunes
2. Shut off iCloud, cell data and WiFi on iPhone; shut off router (it can't hurt to put phone in airplane mode as well).
3. In settings choose General>Reset>Erase all content and settings
4. When phone resets skip entering Apple ID (I told the phone I don't have an Apple ID)
5. immediately shut off cell phone data
6. Start iTunes on your computer. Hit the musical note icon in upper Left. Check the boxes on songs you wish to have on phone
7. Plug iPhone into computer -- DO NOT LET iTUNES SYNC ANYTHING!
8. Click on the phone icon in upper left
9. Select "Music" from the On My Device list on Lower Left, not from the top Settings list
10. Click on "Edit Playlist" on the Right
11. Drag individual checked songs to Music Playlist on right (you may be able to select your entire music library and drag it over. I have heard that only the checked songs will be added to the playlist but I am not positive).
12. My version of iTunes immediately added the songs to my phone. You might have to click "Done" button and/or manually sync depending on your software.
13. Check out your phone-- ALL THE MUSIC IS ACTUALLY RESIDING ON YOUR PHONE! 
14. Restore other files, settings and software.

I am hoping that I don't have to go through all of this each time I want to change up my music. We'll see.

Oh, and be sure to shut of Cellular access to Music in Settings

2 years, 2 annoying years I've been trying to fix this and you fixed it in 8 seconds. You are my Apple HERO!!!!!

Nice to know I could help someone. Kinda makes it worth all the trouble.

I want to start a REVOLUTION against Apple--David turned Goliath!

Thank you for providing this solution.  I had gone through several other steps including erasing my music using both the device and iTunes, and resetting my iTunes Library to no avail.

This worked!  Thank you!

Three years later and that post is still helping. Thanks Jerrill!

I downloaded ifunbox, deleted the purchases folder, logged out of iTunes on my PC and on my phone, logged back in, and guess what?  ALL of the songs on my iphone are grayed out now!!!!!

HELP!!!!!!!!!!!!!!!!!!!!!!!!!!!

The following steps should help, assuming all of the content you want is in your library.

(If it isn't see Recover your iTunes library from your iPod or iOS device.)

1. Backup device.
2. Restore as a new device.
3. Restore the backup you made earlier.

tt2

iFunbox and deleting the purchases worked for me as well... although I did have to hard reboot the phone, this was not mentioned in the original post.

You ROCK! With my new car, the first song on my play list starts as soon as my phone syncs, except it was one of those grayed songs I was done with!!!! They are so gone now! Thank you!

If you did not go to the file/library/organize library, then your files were not copied to your computer. You may need to delete these songs, reload and try the above instructions.

This is the most helpful reply I've ever seen. FINALLY someone was able to offer a legitimate fix. My savior.

Hi people- Actually in some cases (like mine) I think for some reason iTunes is not downloading the file to the iPhone, and rather keeping it in the "cloud."

To fix, I went to Music on my iPhone, selected the red menu in the center (Songs, or artists, etc) then scrolled down and unchecked "Only Downloaded Music"

Additionally it looks like at the top right you can choose "Show All Music"

Then I could find my missing albums, and they had the magic "Cloud with down arrow" icon next to them. I clicked it and it appeared to have downloaded them locally to the iPHone.