I think the current LWP doesn't ask anymore. If a module is well-behaved, it will use ExtUtils::MakeMaker::prompt, which knows when a user is at the terminal and when not. There are badly behaved modules, like (I think) Apache::Request, which will enter a potentially infinite loop asking forever (and again) for the location of httpd. Those modules are badly programmed and nothing short of solving the halting problem will provide a general solution for these.

If you're really interested in an evolving solution, have a look at andk's Distroprefs. He maintains snippets of Expect or other canned behaviour, like answers, patches or settings for many distributions, and you can maintain your private set as well, yourself. They get (almost) automatically integrated into your run of the cpan shell.