Old iTunes music

Hello JeffL007,

Thank you for reaching out to Apple Support Communities, and we'll be happy to help in any way we can. We understand you're having issues with downloading previously purchased music. Try the steps here to see if they resolve the issue: Redownload music - Apple Support

"Learn how to redownload music that you purchased from the iTunes Store.

Redownload music in the iTunes Store app on your iPhone, iPad, or iPod touch

1. Open the iTunes Store app.

• On your iPhone or iPod touch: At the bottom of your screen, tap More , then tap Purchased. 
• On your iPad: Tap Purchased.

1. Tap Music. If you use Family Sharing, tap a family member’s name to see music that they purchased.
2. Find the music that you want to redownload, then tap it.
3. Tap the download button  next to a song or album.

Don't see the music that you purchased?

Redownload music from the iTunes Store in the Apple Music app on your Mac

Before you can redownload music that you purchased from the iTunes Store, you need to authorize your Mac using your Apple ID.

1. Open the Apple Music app.
2. From the menu bar at the top of your screen, choose Account > Purchased. If you use Family Sharing, you'll see Family Purchases instead of Purchased.
3. Find the music that you want to redownload. If you use Family Sharing, choose a family member next to Purchased to see their purchases.
4. Click the download button  next to a song or album.

 Don't see the music that you purchased?

Redownload music in iTunes on your PC

Before you can redownload music that you purchased from the iTunes Store, you need to authorize your PC using your Apple ID.

1. Open iTunes. 
2. From the menu bar at the top of the iTunes window, choose Account > Purchased. If you use Family Sharing, you'll see Family Purchases instead of Purchased.
3. Choose Music from the menu in the upper-left corner of the iTunes window.
4. Find the music that you want to redownload. If you use Family Sharing, choose a family member next to Purchased to see their purchases.
5. Click the download button  next to a song or album.

Don't see the music that you purchased?"

We hope this helps.

Cheers!

Hello JeffL007m

Thanks for checking. Please contact Apple Support to investigate this with you further.

Get Support

Thanks.