The U.S. Department of War (DoW) has great interest in its commitment to eliminating sexual harassment (SH) and sexual assault (SA) within its ranks, including at the military service academies (MSA). A key component of creating a safe environment at the MSAs involves improving the SH and SA programs and resources available. The Contextual Insights from Service Academy Survey Comments study explored qualitative data from existing data collections to glean insights into contextual factors in an effort to understand the decline in rates of SH and SA at the MSAs as measured on the Service Academy Experiences Survey (SAES). Open-ended comments left by cadets and midshipmen across the MSAs from the 2022 and 2024 SAES, as well as a selection of comments from the 2022 and 2024 Defense Organizational Climate Survey (DEOCS), were analyzed using natural language processing techniques to identify key themes in the written responses. Themes identified from this analysis included sexually harassing behaviors, prevention of sexual assault, sexual assault reporting processes, and academy leadership. Overall, the comments suggest that positive changes made at the MSAs have appeared to help drive the decline in experiences of SH and SA.