Software protection is an essential aspect of information security to withstand malicious activities on software, and preserving software assets. However, software developers still lacks a methodology for the assessment of the deployed protections. To solve these issues, we present a novel attack simulation based software protection assessment method to assess and compare various protection solutions. Our solution relies on Petri Nets to specify and visualize attack models, and we developed a Monte Carlo based approach to simulate attacking processes and to deal with uncertainty. Then, based on this simulation and estimation, a novel protection comparison model is proposed to compare different protection solutions. Lastly, our attack simula...