For people with serious mental illness, research demonstrates the potential positive effects of having an advance directive with specific instructions for mental health care. The Commonwealth of Virginia has undertaken efforts to incorporate the completion of psychiatric advance directives into routine mental health services for individuals with serious mental illness. The inherent complexities of advance directives-a single legal tool for use by a heterogeneous array of consumers, providers, and organizations-have led to more barriers than had been anticipated. This article describes challenges encountered in the first three years of implementation efforts. Data are from feedback on early training attempts and experiences of staff at pilot sites and work groups convened for the implementation project. The authors describe a range of challenges, such as how to present a complete and clear message about the nature, purposes, and potential advantages of psychiatric advance directives to various audiences, in particular their use in recovery-oriented care; how to promote cross-system collaboration among potential users of these directives; and how to overcome resource constraints and sustain interest in the process. Virginia's experience reinforces the importance of developing multifaceted implementation strategies, such as the creation of informational and training tools to spread implementation more effectively, the identification of "champions" or staff members who are invested in implementation, and the development of multiple approaches to facilitating completion of advance directives by consumers.