Although this paper would have been ultimately written, much impetus was provided by the Federal Government's (U. S. Custom Department's) investigation into Drink Or Die (DOD), the "underground" software securities group. The following critique on software licensing systems given in this essay is meant to increase the effectiveness of already available software protections by shedding light on their vulnerabilities and strengths. This paper will also attempt to demonstrate how software hackers think, what tools they use, why they attack certain targets, and how to keep software from being "cracked".