The accelerating pace of technological innovation and development is outpacing both employees’ and employers’ ability to maintain the minimum requisite knowledge, skills and abilities to operate effectively. Future cyber workforce development and the continuous training of existing employees will require new and innovative methods for the creation of vehicles for recruitment and engagement of the broadest possible impact. The CyberTRAINsitions workshop, scheduled for December 6th, will bring together representatives from the Department of Defense, academia, and private industry to discuss these challenges and consider potential solutions. Building from the TRAINsitions workshop hosted by the Institute of Simulation and Training in January 2019, CyberTRAINsitions will feature a morning plenary session, a lunchtime student cyber-project poster session, and four breakout special-topic focus tracks covering Cyber Simulation and Training, Cyber Strategy and Policy, Human Aspects of Cyber Security (HACS), and Integrating Women and Underrepresented Communities into the Cyber Workforce.