Cryotherapy is a commonly used topical treatment for various dermatological conditions. Although a generally safe and effective treatment, cryotherapy presents potential adverse risks, including frostbite injury. Frostbite is a vascular condition leading to tissue damage, secondary to prolonged exposure to freezing conditions. Prompt treatment is critical to prevent severe complications, including tissue necrosis and subsequent amputation. Patients with predisposing risk factors, such as vascular conditions that impede blood flow, may pose a higher risk of cryotherapy-induced complications. Additionally, military personnel who endure extremely cold environments are especially vulnerable to developing frostbite and other cold-weather injuries. We herein present a documented case of iatrogenic frostbite in a 23-year-old active-duty United States Navy sailor who required a diverse range of treatment modalities including pain management, sildenafil, nitroglycerine paste, and hyperbaric oxygen therapy. The treatment regimen provided significant clinical improvements, with minimal long-term structural damage. This unique clinical presentation underscores the need for delineated treatment guidelines: best practices for safe cryotherapy administration and ideal dosing amounts to minimize adverse sequelae.