How do I re download music Ive purchased in 2014
Where’s my music from 2014?
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Redownload apps, music, movies, TV shows, and books - https://support.apple.com/HT201272
Are you trying to re-download using the same Apple ID?
Also read the fine print:
Legal - Apple Media Services - Apple - https://www.apple.com/legal/internet-services/itunes/us/terms.html - "DOWNLOADS You may be able to redownload previously acquired Content (“Redownload”) to your devices that are signed in with the same Apple ID (“Associated Devices”). You can see Content types available for Redownload in your Home Country at https://support.apple.com/HT204632. Content may not be available for Redownload if that Content is no longer offered on our Services." Always download everything and keep multiple backup copies on local storage.