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Herpetic whitlow is a viral infection of the fingers or toes caused by the herpes simplex virus. Herpes simplex virus is a common pathogen that causes infections in any cutaneous or mucocutaneous surface, most commonly gingivostomatitis or genital herpes. However, infection of the digits is also infrequently reported. Herpetic whitlow occurs when the virus infects the distal phalanx of the fingers or toes by means of direct inoculation, causing pain, swelling, erythema, and vesicle formation. The proper diagnosis is important because the condition can mimic various other podiatric abnormalities such as paronychia, bacterial cellulitis, or even embolic disease. Improper diagnosis often leads to unnecessary work-up, antibiotic therapy, or even surgical intervention. This case will help illuminate the clinical presentation of herpetic whitlow in an atypical location, and the patient’s subsequent treatment. We present an atypical case of right hallux herpetic whitlow with delayed diagnosis and associated cellulitis. The patient was admitted after seeing multiple providers for a progressive right hallux infection that presented as a mixture of vesicular lesions and apparent cellulitis. His history was positive for biting his fingernails and toenails, and the lesions were noted to be honeycomb-like, with minimal drainage. The lesions were then deroofed and viral cultures were obtained, which were positive for herpes simplex virus type 1, thus confirming a diagnosis of herpetic whitlow. Although he remained afebrile with negative wound cultures during admission, a secondary bacterial infection could not be excluded because of his nail avulsion and surrounding cellulitis. He was discharged on oral antibiotics, antivirals, and wound care recommendations. Herpetic whitlow should be included in the differential diagnosis of pedal digital lesions that appear as vesicular or cellulitic in the pediatric population.