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But since I didn’t have an account myself aren’t the locked ones (admittedly they unlock in your scenario) registered only to my friend (who I reimubursed)? Of course they would only report if they actually played I think.

But once they're converted to AIFF by burning them onto a CD and reimported as MP3, they don't carry any registration information. I wasn't able to play on PSP a bunch of stuff I bought from the iTunes store so I just burned the CD, imported it as high quality MP3s, and then dragged and dropped them into the PSP music folder. Problem solved.

I wasn't able to play on PSP a bunch of stuff I bought from the iTunes store so I just burned the CD, imported it as high quality MP3s, and then dragged and dropped them into the PSP music folder.

A tip for retaining quality for your original versions: Re-import as Apple Lossless and you don't lose any quality but you now have non-DRM version in iTunes. You can later convert to MP3 for other devices, but you do lose quality. IIRC, the PSP also does AAC, so try that to get some better quality than MP3.