Solution to iTunes files purchased years ago with different email addresses/Pwords that now won't play

Although I may not be able to help, I understand your frustration. All I can do is suggest what works for me and I've been doing this for over twenty years.

To be clear, if you purchased your iTunes content under a different Apple Account (formerly known as Apple ID) then only that Apple Account will be entitled to the privilege of playing that content. Be sure you understand that distinction because it is critical to understand what follows.

For all practical purposes an "Apple Account" is you. As far as Apple is concerned, "you" = your Apple Account. Of course "you" have more than one "you" but only if separate and unique Apple Accounts were created for each one of them. That is never a good idea. One person, one Apple Account is the unwritten rule.

I bought and paid for these songs!

Understood. They are "yours" but only in the context I just explained.

Now... once that point is made abundantly clear, it's perfectly ok and expected that the email account used to create that Apple Account may change from time to time. When changing your email service provider (for example) you must change it within your Apple Account. Never create a new Apple Account. Instead, change the email address associated with it.

That is all explained here: Change your Apple Account primary email address - Apple Support.

If you did that, then all is well and you will not lose access to any previously purchased iTunes content. However, if you purchased that content under a different email address than the one you're using now, upon attempting to play that long ago purchased content you may be harassed to provide your Apple Account credentials multiple times. That can understandably lead you to suspect something is amiss, and that iTunes is looking for earlier email address(es) that simply do not exist anymore — as you wrote. Not so. In that case what I do is to type the password in plain text in Notes or TextEdit or whatever, cut it, and then paste it in the password field as many times as required to placate the nag. In some cases that may mean a dozen times or more, depending on how much content you purchased and under how many different email addresses.

Use this information as you see fit — as I wrote, all I can do is tell you what works for me.

The credentials that you use when you buy or subscribe to something within the Apple environment are the combination of email and password. That is the 'receipt' that is used to authorize your computer and devices to use these purchased files.

The bottom line here is that without the 'receipt', Apple cannot do anything to help you.

Back in the day, Apple was constrained by agreements with the copyright owners and publishers to create and use DRM security on its music store offerings. These agreements were required and allowed Apple to change the music landscape at the time.

You will probably find that bypassing the security placed on early Apple music files, that you cannot authorize, is not easy.

If you are talking about 128 Kbps AAC files with DRM, you are probably hosed. Those are the type of files that the iTunes Store sold up until some time in 2009.

If you are talking about 256 Kbps AAC files that do not have DRM, but that do include metadata that identifies the purchaser, I hope that Apple would not be enforcing any authorization nonsense on them, with regards to playing copies that are already on your machine. (Redownloading those purchases would require having the appropriate Apple Account credentials.)

Apple never removed DRM from music videos, or movies, or TV shows, so if you have any of those that you bought or redeemed ("Movies Anywhere", "Digital Copies"), the above doesn't apply to them.