Windows taught me that Debian was in this instance 100% correct. I noticed that even though my computer was configured to take updates automatically, the system tray icon indicating updates were available to install had been around for a few days. I clicked on it only to find that critical updates were waiting for me to assent to their license before they installed. Um, no, just not OK. I never want to have to go around to all the managed computers in an organization and agree to a bunch of licenses just to avoid security problems. Anything that gets in the way of automatic upgrades for the sake of licensing is not acceptable.
The obvious next stand is to argue that the software should wait for assent when it is run not when it is installed. Unfortunately that just doesn't work for libraries. I'm picturing a situation where your display manager attempts to open an X connection so it can present the login window only to be told that X will not be available until the user assents to the latest license in the font rendering engine.