Kaposi sarcoma (KS) is a malignancy of viral etiology whose course ranges from cutaneous limited lesions to fulminant disease with multi-organ involvement. Four clinical variants of the disease exist: classic, endemic, iatrogenic, and epidemic. Iatrogenic and epidemic variants of Kaposi sarcoma develop in the setting of immune suppression. Transplant recipients who develop iatrogenic KS typically demonstrate improvement of lesions following de-escalation of immunosuppressive therapy. Similarly, HIV-infected patients who begin highly active antiretroviral therapy (HAART) experience immune reconstitution, which can induce KS regression. We describe two patients with varying clinical outcomes of cutaneous-limited HIV-associated KS after immune reconstitution with HAART. We propose that immune reconstitution with HAART, followed by clinical and radiographic surveillance for disease progression, may be an appropriate initial management strategy for limited cutaneous HIV-associated KS. In patients with more extensive disease at presentation or failure of HAART alone, antineoplastic therapy should be instituted.