Strong evidence supports the efficacy of cognitive behavioral therapy for insomnia (CBTI). A significant barrier to wide dissemination of CBTI is the lack of qualified practitioners. We describe challenges and decisions made when developing a CBTI dissemination program in the Veterans Health Administration (VHA). The program targets mental health clinicians from different disciplines (psychiatry, psychology, social work, and nursing) with varying familiarity and experience with general principles of cognitive behavioral therapies (CBT). We explain the scope of training (how much to teach about the science of sleep, comorbid sleep disorders, other medical and mental health comorbidities, and hypnotic-dependent insomnia), discuss adaptation of CBTI to address the unique challenges posed by comorbid insomnia, and describe decisions made about the strategy of training (principles, structure and materials developed/recommended). Among these decisions is the question of how to balance the structure and flexibility of the treatment protocol. We developed a case conceptualization-driven approach and provide a general session-by-session outline. Training licensed therapists who already have many professional obligations required that the training be completed in a relatively short time with minimal disruptions to training participants' routine work responsibilities. These “real-life” constraints shaped the development of this competency-based, yet pragmatic training program. We conclude with a description of preliminary lessons learned from the initial wave of training and propose future directions for research and dissemination.