Kaposi sarcoma is a malignancy evolving from the lining of blood and lymphatic vessels. It is caused by the reactivation of human herpesvirus 8, often due to underlying immunosuppression. Classic Kaposi sarcoma occurs in Eastern European males greater than 50 years of age as painless violaceous papules to nodules. We report a case of a 63-year-old man with severe Kaposi sarcoma first diagnosed on the right medial foot with progressive involvement of upper and lower extremities. It was managed with monthly rounds of excisional cauterization, electrodesiccation, cryotherapy, and 5% imiquimod topical cream, leading to overall improvement and avoidance of amputation. However, a year later the patient presented with bullous pemphigoid on the left distal upper arm, suprapubic skin, and right and left pretibial regions. After three months of treatment with mycophenolate mofetil, prednisone, triamcinolone, doxycycline, and clobetasol, the patient's bullous pemphigoid stabilized. Hence, the simultaneous presentation of bullous pemphigoid and Kaposi sarcoma displays a unique problem in the management and treatment of dermatological conditions. Kaposi sarcoma is exacerbated through immunosuppression, whereas bullous pemphigoid treatment requires immunosuppressants. Extensive excisional therapy and cryotherapy for Kaposi sarcoma, alongside careful management of immunosuppressants for bullous pemphigoid, is critical for managing optimal care in concurrent cases. Further research should be performed to better understand the causal interplay of Kaposi sarcoma, imiquimod, bullous pemphigoid, and other dermatological issues requiring immunosuppressant treatment.