Q: Download all purchased music from iCloud.

Hey thanks, kpizle.  I was having this same problem after a system crash and wanting to re-download all my stuff from itunes match, and your solution, which I initially missed despite the fact it really should have been blindingly obvious, worked perfectly. 

It’s just plain stupid that the Download All button doesn’t download all songs for everyone. If you’ve bought less than 2000 songs, the list of recent purchases will show every purchase and Download All does indeed download everything. If you, however, have invested more money in your music collection you only get 250 songs at a time from the list of recent purchases. Confusing, inconsistent, and entirely unnecessary by Apple. It creates tempered and frustrated forum threads like this one for no reason what so ever. You can still download everything in one go but you have to go about it in a weird way that is non-intuitive. Especially because you have to sit and wait for an empty view (with no progress indicator) is downloaded and starts filling up with your music collection. To be fair, iTunes downloads all metadata and albumart for all your songs in this process. This is a significant chunk of data so it stands to reason that it will take time. But like everything in this process, it adds to the feeling of frustration.

Remember to backup your iTunes libraries! iTunes in the Cloud could disappear day, according to Apple’s terms of service. You can’t really on it saving you every time until infinity.

I tried the download all and am being prompted for my password on each song...

Is there a way to get the music I purchased (not many, but, more than I want to re-enter my password for) w/o having to enter my password for each song?

Apparently if you select the remember password for free content it will proceed w/o prompting for password after each song...problem fixed.

I just found the solution and thought I'd share for version 12.2.1.16.

Music (top left) > iTunes Store (top middle) > Download All (bottom right)

Sign in with Apple ID. Choose 15 minutes for purchases on computer.

Ta-da!!

I spent some time with this issue as well.  I finally came across a resolution and hope this helps. Simply type in the search bar "All Albums" while doing an album search and then click "download all" in the lower right.

iTunes/iClous is not an intuitive setup and has long been so. 

Hope this helps!  

This works for windows too if you ctrl+a then right-click and press make available offline! Make sure you don't have anything else downloaded otherwise that option won't show. instead you will see "remove downloads". But you can just press that, then try again.

this is actually pretty annoying ! I didn't find a solution rather a short cut I suppose. If you go to your music then select genre then make available offline it should make is a lot easier ! youll have to do it for each genre but it could save you 3000 clicks lol

Thanks! this worked perfectly! The option is actually called "Make available offline" in the latest version of iTunes

Genius.

@cjsporl I am using the Windows version 12.4.3.1 and do not see "show iTunes in the Cloud purchases" in Preferences > Store

@macman44 No, as already said by my fellow frustrated users, the Download All button only downloads the most recent purchases (or 'what's on the screen')

@kpizle The problem is getting them into the library or 'My Music' first.

I think cjsporl might be on the money here.  Perhaps it's due to being the Windows version?