Billions of dollars are lost to software piracy each year, this figure being proportional to our security software. This essay will focus and analysis on current existing protection methods of security software, ranging from anti-dump, anti-trace to virtual machines. It will analyze each protection feature for strengths and weaknesses and present a holistic analysis of modern security protection mechanisms. These protection methods will be tested against modern live analysis tools actively used by the reverse engineering community today. Unorthodox methods may be used as reverse engineers have a variety of options as they are the end-users. The protection schemes will be compared relative to their difficulty of implementation, run-time deficiencies (only applies to virtual machines), and their ability to hinder or stop reverse engineering processes, each of the schemes looked analyzed on an implementation and execution basis. The findings are shocking but in check with our modern markets and community today; it is shown that current software defense methodologies are not up to standards, their protection can be easily circumvented and the exorbitant price tag of software piracy is to be expected.