Patients who are infected with human immunodeficiency virus (HIV) are at increased risk of developing laryngeal squamous cell carcinoma. This malignancy on average appears in a younger age group at a more advanced stage and has a more aggressive course in HIV patients. These patients have difficult management challenges, diagnostically, in staging, and particularly in determining the optimal treatment for each individual patient because their underlying HIV infection can markedly increase morbidity associated with active treatments. They frequently have problems associated with swallowing both before and after treatment. We present two cases that highlight difficulties in the diagnosis and management of these patients as well as post-treatment complications, with particular emphasis on swallowing problems.