Background: Female service members tend to have a higher level of foot injuries than males. The United States Army spent $103 million in 2017 on fractures in toes and feet. Fractures of the tibial and fibular sesamoids are problem that often can be nonspecific, mainly related to pain at the plantar aspect of the first metatarsal head without an obvious traumatic event. Anatomic variation in these sesamoids exist after ossification which results in the possibility of multipartite sesamoids. Of the multipartite sesamoids, bipartite sesamoids are the relatively common and tripartite sesamoids are quite rare. The overall prevalence of bipartite sesamoids is presumed to be between 7 and 30%, with a majority occurring bilaterally. Methods: We completed a case series on three female active-duty Airmen. All three patients were active with their pain beginning following activity. All three were subsequently misdiagnosed, resulting in at least 6 months of pain prior to diagnosis and treatment. Results: Plain film radiography and subsequent imaging confirmed the diagnosis of a tibial or fibular sesamoid fracture. Following conservative treatment all three patients made a full recovery as confirmed by imaging and self-reported pain levels and they were able to return to full activity. Conclusion: Providers should keep a sesamoid fracture in the differential diagnosis when evaluating active female patients with pain in the area around the base of the great toe, especially in women in the military and others that may do higher levels of physical activity compared to the average patient. While the diagnosis of sesamoid fractures can be challenging, it is standard practice to obtain multiple views if using plain film radiography. Magnetic resonance imaging, weightbearing computed tomography and bone scans can be useful confirmatory studies.