Successful flight crew team performance in today’s advanced technology cockpits is essential for mission accomplishment and contingent on crewmembers monitoring each other and providing the appropriate backup (Kontogiannis & Malakis, 2009; Tullo, 2010). Flight crew monitoring can serve as the last line of defense against aviation accidents and monitoring failures are evident in many recent accidents (Dismukes & Berman, 2010; FAA, 2017). In our study, thirty U.S. Coast Guard cockpit flight crews flew automated and non-automated instrument takeoffs as both pilot flying and pilot monitoring in the Coast Guard’s MH-65 Operational Flight Trainer. We explored the effects of shared situational awareness, aviation experience, and level of cockpit automation on monitoring and backup performance. Instructor pilots observed the interaction of the cockpit flight crews to evaluate the level of monitoring and backup during the nighttime overwater instrument takeoffs. Based on the study’s findings, the U.S. Coast Guard is redefining monitoring and backup in aircraft cockpits, defining critical behaviors for effective cockpit automation management, and changing how Coast Guard pilots are trained and evaluated to successfully perform in advanced technology multi-piloted cockpits.