Lower-extremity ulcerations have an estimated prevalence of 1%-2% in the United States and are a common cause of inpatient hospitalization. A systematic approach beginning with the most frequent etiologies is essential to avoiding misdiagnosis and excessive health care expenditure, as more than 90% of cases may be explained by chronic arterial or venous disease alone. The differential diagnosis for the remaining minority of non-healing leg ulcers is extraordinarily broad and includes infection, panniculitis, calciphylaxis, vasculitis or other immune-mediated etiologies (eg, neutrophilic dermatoses such as pyoderma gangrenosum or Behçet disease), and malignancy, among numerous other causes. Herein, we present the case of a 36-year-old woman with a several year history of bilateral lower extremity erythema nodosum (previously responsive to prednisone tapers and hydroxychloroquine) and bilateral leg ulcerations secondary to thrombotic vasculopathy (confirmed on skin biopsy), known chronic venous insufficiency, steroid-induced diabetes mellitus, and obesity was admitted to our hospital with acute on chronic worsening of longstanding leg ulcerations. Physical examination was notable for two large bilateral lower extremity ulcerations accompanied by faintly erythematous, blanching macules and papules coalescing into patches and plaques on the bilateral thighs as well as oral and genital ulcerations. Laboratory evaluation was notable for leukocytosis of unclear significance in the setting of high-dose systemic corticosteroid administration. A repeat skin biopsy revealed an intravascular lymphoid infiltrate ultimately consistent with T-cell prolymphocytic leukemia (T-PLL). Our case demonstrates the importance of repeat skin biopsy in cases of atypically presenting, recalcitrant to therapy, or acutely worsened lower extremity ulcerations.