iTunes Match and Apple Music both allow you to sync up your tracks to your iCloud Music Library, where you can can stream and download them to any iPhone, iPad, Mac, or Apple TV without having to take up physical storage space.
While both services are incredibly convenient when they work, they aren't completely error-proof either. Whether they're hanging up while trying to sync, or your music isn't showing up on your iPhone or iPad, here are some steps you can take to try and remedy your issue.
1. Check iCloud's service status
Sometimes Apple does routine maintenance on specific iCloud services. If you're getting stuck with iCloud Music Library giving you an endless "Sending information to Apple" error, this is most likely the reason. Before trying to log in, log out, or troubleshoot elsewhere, try checking Apple's Services, Stores, and iCloud system status website.
If the indicator next to Apple Music, iTunes Match, and iTunes in the Cloud is green and you're still having trouble, try the next step listed below. If it's showing up as yellow or red, Apple may be doing a system update; check the status page again later.
2. Turn iCloud Music Library on and off on all iOS devices
If you're having an issue with iTunes Match appearing on , or if you're missing a bunch of stuff that should be there, turning it on and off again in Settings could resolve the issue.
Open the Settings app and go to Music.
Disable the iCloud Music Library switch.
Turn back On the option for iCloud Music Library and when prompted, tap on Enable.
Launch the Music app.
If you still aren't seeing the music you want synced, there may be a problem with iTunes. Continue on to the next step to try and resolve it.
3. Update iCloud Music Library within iTunes
Even though iCloud should update itself regularly, there are occasions that it doesn't happen for one reason or another. Before trying anything else within iTunes, try updating your iCloud Music Library manually.
In iTunes, go to File > Library > Update iCloud Music Library.
The Activity dialog will appear in the upper right corner, tracking iCloud Music Library's status.
Any tracks listed as "Waiting" should shortly be uploaded or matched to the iTunes/Apple Music catalog (depending on whether you have iTunes Match or Apple Music).
4. Turn iCloud Music Library on and off in iTunes
If you absolutely want to force iCloud Music Library to re-sync all your music, turning it on and off is the way to go. I'd recommend this step for anyone who is experiencing freezes or hangups when trying to sync with iTunes Match or Apple Music, especially if you've already tried all the above steps. Just be aware that your whole library may have to be scanned again and, depending upon its size, this could take hours or even days.
On your Mac, go to the iTunes menu and select Preferences.
In the General tab, uncheck the box next to iCloud Music Library.
Repeat the same process, but re-enable iCloud Music Library.
5. Sign in and out of iTunes on all devices
If simply turning iTunes Match itself off and then back on doesn't seem to fix the issue, try signing out of iTunes completely on all your devices, including your Mac or PC. Then sign back in and try syncing your iCloud Music Library again.
On your Mac or PC, launch iTunes.
Select the Account menu at the top.
Click Sign Out.
Repeat the same process, but sign in.
Follow the prompts to re-enable iCloud Music Library.
More iCloud Music Library help
If you're still experiencing trouble with iTunes Match, Apple Music, and iCloud Music Library after trying all of the above steps, our iTunes forums are a great place to ask for help. If you still can't find what you're looking for, it may be time to contact Apple to see if they can directly solve your problem.
Ally Kazmucha contributed to an earlier version of this article.