If I repurchase a formerly DRM protected album, will I get it without DRM?

Mapachusetts,

Assuming you are still using the same Apple ID as the original purchase, the iTunes Store will not let you buy it again. It will say Play instead of giving the price. (Go ahead and verify this in the Store.)

You can buy an unprotected copy from a different music download store and add it to your iTunes/Music library, and delete the DRM-infected copy.

As U recall, it was Apple that convinced the record companies to sell music in electronic form at all.

All of the early music services that had major label music used DRM. When the record companies allowed Amazon and Apple to sell music without DRM, Apple dropped it, and offered the ability to upgrade many DRMed songs to non-DRMed ones (for a fee). The reason you don’t remember the other “services” is that they withered and died instead of making a transition to be competitive and DRM-free.

Songs that you buy from the ITunes Store and Amazon MP3 Store are still internally marked to identify you as the purchaser, although they do not contain DRM.

The behavior you are seeing suggests that iTunes/Music thinks it is a different album than the old one you bought, e.g., remastered. That message about transferring is annoying, but at least you got the new unprotected version. :-)

I would think rhat you would want it to transfer copies of the purchased files back to the computer.

How does it shackle you to have the music on the computer as well as on the phone?