The U.S. Air Force’s (USAF) aeromedical evacuation (AE) team and Critical Care Air Transport Team (CCATT) are vital components of the military’s medical evacuation mission, transporting wounded, ill, and injured military members to (and between) medical facilities throughout various parts of the globe. The performance, readiness, and health of such airmen are essential to a wide range of combat and humanitarian-based operations. The goals of the study are to (a) assess self-reported behaviors relevant to sustaining health, medical conditions perceived to be created or made worse by their current assignment, and noted changes in usage of medical, mental health, and alternative health services and prescription/over-the-counter medications; and (b) identify differences in these behaviors and conditions between AE and CCATT members who function in deployed settings to provide critical aeromedical care to military personnel. All AE and CCATT crew members were sent surveys, which were anonymous, voluntary, and self-report. A total of 251 AE and CCATT crew members completed the web-based survey, 168 (66.93%) of which were AE crew members, while 83 (33.07%) were CCATT crew members. The response rate for this study was estimated at 40% for AE and 37% for CCATT. A number of recommendations are provided for line and medical leadership for optimizing health and improving performance for both AE and CCATT members, including, but not limited to, the following: considering ways to decrease occupational stress and increase awareness of social climate issues for sustaining effective team performance, understanding and reducing barriers to behaviors that promote health, as well as embedding mental health providers within the respective units for increasing access to specialty mental health care.