Cybersecurity is a constant, and, by all accounts growing, challenge. Although software products are gradually becoming more secure and novel approaches to cybersecurity are being developed, hackers are becoming more adept, their tools are better, and their markets are flourishing. The rising tide of network intrusions has focused organizations' attention on how to protect themselves better. This report, the second in a multiphase study on the future of cybersecurity, reveals perspectives and perceptions from chief information security officers; examines the development of network defense measures, and the countermeasures that attackers create to subvert those measures; and explores the role of software vulnerabilities and inherent weaknesses. A heuristic model was developed to demonstrate the various cybersecurity levers that organizations can control, as well as exogenous factors that organizations cannot control. Among the report's findings were that cybersecurity experts are at least as focused on preserving their organizations' reputations as protecting actual property. Researchers also found that organizational size and software quality play significant roles in the strategies that defenders may adopt. Finally, those who secure networks will have to pay increasing attention to the role that smart devices might otherwise play in allowing hackers in. Organizations could benefit from better understanding their risk posture from various actors (threats), protection needs (vulnerabilities), and assets (impact). Policy recommendations include better defining the role of government, and exploring information sharing responsibilities.