The National Association of School Psychologists developed the "PREPaRE School Crisis Prevention and Intervention Training Curriculum" to help schools plan for and prevent school crises and to help mitigate the effects after a crisis occurs. In this study, 279 participants who attended the PREPaRE training between 1 and 24 months before the survey date completed measures assessing work environment, trainee characteristic, and training design variables as well as the transfer of PREPaRE-specific knowledge and skills. Utilizing structural equation modeling, unique effects of Work Environment and Trainee Characteristic variables on knowledge and skill transfer and the extent to which Trainee Characteristics moderate effects of the Work Environment were assessed. Results indicated a significant moderating effect such that trainees who were less motivated compared to those who were more motivated demonstrated greater transfer when they worked in more supportive, open, and rewarding environments. Overall, results from this study provide evidence to support addressing many individual and contextual variables to improve the transfer of PREPaRE-specific knowledge and skills. Implications for practice are discussed.