Senior leaders rightly expect defense systems to be reliable and experience supports this expectation. However, todays competitive electronics design and manufacturing environment has led to components and software equally sourced by military and commercial entities. These technologies are in the supply chain of Critical Defense Systems. Wide availability permits reduced cost and increased communication, but also opens access to subversion by an Advanced Persistent Threat. Senior leaders must consider including trust as a design discipline. Senior leaders resist focus on trust because its complex, dynamic, and non-data driven. Trust has interdependent elements that place it in the category of a Wicked Problem, one whose requirements and solutions are always changing. Research for this paper included a review of internal and external literature to understand human responses to trust; wicked problems; the relationship between trust and current technology, quality assurance and production practices; and examples of successful subversions of the past. The paper concludes with how the three principles of trust, prevention, detection, and mitigation, may be implemented, and presents paths for senior management to establish trust and resolve wicked problems.