Subscription required for access to full text of most articles, but I wanted to point out a couple of articles that you might find it worthwhile to track down:

What Hackers Learn that the Rest of Us Don't: Notes on Hacker Curriculum

The hacker culture has accumulated a wealth of efficient practices and approaches to computer technologies -- in particular, to analysis, reverse engineering, testing, and software and hardware modification -- that differ considerably from those of both the IT industry and traditional academia.

The above article references the article by Greg Conti that appears in the same issue as Academic freedom and the hacker ethic. It also references a book by Jonathan Rosenberg, How Debuggers Work.

The End of Black and White, by Dan Geer

It's no longer just black hats or white hats in computer security. The more someone has to lose, the less likely they should be to trust the computer. It means that all people, all programs, all transactions are shades of grey. Black and white are just a memory.

This one appears to be freely available:

Estimating Software Vulnerabilities

Any given piece of software has some number of publicly disclosed vulnerabilities at any moment, leaving the system exposed to potential attack. A method for identifying and analyzing these vulnerabilities uses public data from easily accessible sources.

Latest Issue of IEEE Security & Privacy