“My hard drive crashed and I lost all my iTunes music, including about $1000 worth of songs I purchased from iTunes Music Store. I’m already stuck re-ripping a bunch of CDs but what about all those songs I paid for? Can I re-download songs purchased from iTunes or am I out of luck?”
Sorry to hear about your data disaster. Losing files is never fun and I don’t envy you having to rip those CDs. Hopefully I can offer some good news for you with regard to those songs you paid for from iTunes. You can redownload music purchased from iTunes, they just don’t make it easy.
For a long time, Apple did not allow users to redownload songs purchased from iTunes. Thankfully, they changed their policy. You can now download music on up to 10 computers or devices authorized for your account. For most people, that should be plenty since that would mean downloading to any MacBook, Windows PC, iPad, or iPhone in your collection.
There could be a few rare cases where the songs you purchased are no longer available from Apple. In those cases, you won’t be able to redownload them.
First make sure your computer is one of those authorized devices for access to Apple Music.
Once your computer is authorized in Apple Music, you can check for available downloads by selecting Account > Family Purchases. You should see a full list of all purchased songs and albums available for redownload. At this point, you can either choose Download All to restore everything you previously purchased or choose individual songs and albums.
I also strongly recommend taking an additional step and implement a backup plan. This will save you time in needing to re-rip CDs if you ever have another hard drive failure. One option is to use a cloud service like iCloud, Dropbox, Google Drive, or OneDrive to back up files. The other alternative is to purchase an external hard drive and some affordable backup software. I know plenty of people who have lost data because they didn’t back it up the first time – a second time shouldn’t happen if you create a backup plan for the future.
