Introduction Simulation is a key aspect of the military unique curriculum at the Uniformed Services University (USU). The Department of Military and Emergency Medicine conducts rigorous high-fidelity simulations for military medical students during each year of their medical school training: Patient Experience (first year), Advanced Combat Medical Experience (second year), Operation Gunpowder (third year), and Operation Bushmaster (fourth year). There is currently a gap in the professional literature regarding students’ progression through each of these simulations. This study, therefore, explores the experiences of military medical students at USU in order to understand how they learn and develop as they progress through these high-fidelity simulations. Materials and Methods Using a grounded theory approach to qualitative research design, we analyzed qualitative data from 400 military medical students across all four years of military school who participated in the four high-fidelity simulations during 2021–2022. Our research team used open and axial coding to categorize the data and to make connections between each of these categories, which we articulated in a theoretical framework and illustrated in a consequential matrix. This research was approved by the Institutional Review Board at USU. Results During Patient Experience, the first-year medical students described the stress, chaos, and lack of resources that military physicians face as they experienced the realism of the operational environment. Later at Advanced Combat Medical Experience, the second-year medical students practiced their medical skills hands-on for the first time in the simulated stressful operational environment. As a result, they gained confidence and began to formulate their professional identity. Next, at Operation Gunpowder, the third-year medical students advanced to more complex tactical field care as they performed prolonged casualty care, forward resuscitative care, forward resuscitative surgical care, and en route care as a team, often revealing gaps in their knowledge that needed to be filled. During the capstone simulation, Operation Bushmaster, the fourth-year medical students closed these gaps and solidified their professional identity as leaders and physicians, culminating in a strong confidence regarding their readiness for their first deployment. Conclusions Each of the four high-fidelity simulations impacted the students in unique ways as they were incrementally challenged to practice and build upon their knowledge, skills, and abilities related to combat casualty care, teamwork, and leadership in the operational environment. As they completed each of the simulations, their skills improved, confidence grew, and professional identity solidified. Therefore, completing these rigorous simulations progressively over the course of 4 years of medical school appears to be a vital process and foundation for the deployment readiness of early-career military physicians.