Introduction Medical physician residency program websites often serve as the first contact for any prospective applicant. No analysis of military residency program websites has yet been conducted, in contrast to their civilian counterparts. This study evaluated all military residency programs certified by the Accreditation Council for Graduate Medical Education (ACGME) 2021-2022 to determine program website comprehensiveness and accessibility and identify areas for improvement. Materials and Methods A list of military residency programs in the USA was compiled using Defense Health Agency Graduate Medical Education resources together with the ACGME database. A total of 15 objective website criteria covering education and recruitment content were assessed by two independent evaluators. Accessibility was also scored. Programs’ website scores were compared by geographic location, specialty affiliation, type of institution partnership, and program size. Analysis was performed with descriptive statistics and comparison via an unpaired t-test or Kruskal–Wallis analysis, as appropriate. Results A total of 124 military residency program websites were evaluated with a range of scores from 0 to 15 out of 15 possible points. Six programs had no identifiable website. All three services were represented with 43% joint-service programs. Content concerning physician education and development was more widely available than content directed toward the recruitment of applicants. The number of residency program websites reporting each content criterion varied greatly, but overall, no single service had a significantly higher score across their residencies’ websites. Significant variation occurred among individual specialties (P < .05) but there was no significant difference in surgical and nonsurgical specialties. Civilian-associated programs (18 programs, 14.5%) were associated with significantly greater website comprehensiveness scored best on informatics measures for recruitment and performed 64% better than military-only programs overall. Conclusions Program information in an accessible website platform allows prospective applicants to gain comprehensive perspectives of programs during the application process without reliance on personal visits and audition rotations. Limitations to in-person experiences, such as those caused by reductions in travel and concern for student safety during the global pandemic caused by the SARS-CoV-2 virus, may be alleviated by accessible virtual information. Our results indicate that there is opportunity for all military residency programs to improve their websites and better recruit applicants through understanding their audience and optimizing their reach online.