Recent iTunes song downloads not playing

I have recently downloaded numerous songs and albums from iTunes to Apple Music.


These recent downloads are (seemingly arbitrarily) becoming non-functional.


I download the song or album, and it plays on Music as expected.


Then, at some point in the relatively near future, it stops working.


  • It's visible in Music
  • The file is present in the hard drive folder with other functioning songs
  • Trying to play the song does not work - as in clicking the "Play" arrow has no effect
  • If these songs are synced to my iPhone 6S, they fail to play and a "Cannot open media damaged" error appears.
  • This has not happened to any music burned from discs as far as I can tell (substantial sample size)
  • I am pretty sure it is only affecting music downloaded through iTunes in the past month or so
  • I can delete the music and re-download it, and it will work for a while, but then the issue reoccurs, repeatedly
  • I have run "first aid" through the disc utility on the external drive that is hosting all of the music, and it is functioning fine, no issues



I have paid a substantial amount of money to Apple to download this music, and it is not playing properly.


I am also attempting to maintain an Apple Music subscription in case Apple is requiring that to continue to license ongoing use for paid downloads, but that has no effect. (If this is the case I will only buy CDs and burn them going forward! That seems like an exploitive business model.)


Does anyone have any advice as to how I can resolve this issue?


Thank you-

iMac (2017 – 2020)

Posted on May 7, 2024 7:01 PM

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May 10, 2024 11:14 AM in response to Stephmoto

I have narrowed this issue (a little) to a culprit:


Purchased AAC files are problematic resulting in duplicates and/or not playing after the machine is restarted.


The solution seems to be


  • Delete non-functioning Purchased AAC from the Library
  • Re-downloading these files, DO NOT RESTART THE MACHINE!
  • Convert the Purchased AAC files to AAC files
  • Delete the Purchased AAC files and hide them so they don't continue to cause problems


I have literally thousands of songs in my Library with varying states of duplication and "corruption" leading to unplayable music (without days of work scrubbing duplicates and replacing Purchased AAC Files manually)


If I could go to another platform, I would, but I have thousands of dollars invested in unconvertible Apple platform specific files that I paid Apple for.



Where are the Apple software engineers on this? This is really unacceptable!

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Recent iTunes song downloads not playing

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