How do I get Lossless audio files of the music I bought?

Blorp,

The preferred outlet for "small cool artists" is Bandcamp. They sell downloads in a choice of formats, including lossless. If they have what you want, you can buy downloads there, and add the tracks to your iTunes library.

blorp1 wrote:

Official answer is "not with windows", how else?

LOL, not sure where you got that "official" answer from.

For the real official answer, go to this Apple support doc => About lossless audio in Apple Music - Apple Support

and read the section about "How to listen to lossless on your PC."

Hi,

Music purchased from iTunes Store is 256 Kbps AAC and can’t be upgraded to lossless as Apple does not sell such format.

With an Apple Music subscription, some purchases maybe available to stream or download as lossless but those tracks have DRM and are only available as long as you have an active subscription. If you want lossless music, you will need to purchase CD or digital lossless download from other sources.

Jim