Well in the case of the CrossWorks package they make you sign an agreement and send that in before they will give an activation code for the software. I'm sure that the large part of "enforcement" is the good conscience of the licensee. Maybe from time to time they do spot check web searches looking for products appearing or monitor web forums for certain types of comments.

From what I've read on the web there is also some type of usage license you need to put in place to be able to use the Segger EDU adapter. Since I've not purchased that I'm not fully aware of how the activation for the J-Link EDU actually works.

One does have to get some type of adapter though so the debugger in any package will be useful.

Michael Karas