In recent years, the problem of managing comorbid patients with HIV infection has become increasingly important. The association of chronic dermatoses with HIV infection can significantly change their clinical presentation and course and complicate diagnosis and treatment. However, current antiretroviral therapy can substantially reduce this negative impact. Changing the typical course of chronic dermatoses with a tendency to aggravation and persistence, together with adverse medical and social aspects, are alarming factors and require in-depth testing for HIV infection. Clinical cases of HIV-associated dermatoses are presented. The paper highlights the features that can raise suspicion of HIV infection at the early stages of dermatosis. The changes in the course of dermatoses during antiretroviral therapy are described. The above examples demonstrate the modification of the clinical presentation of the skin lesions in comorbid HIV infection and the need to solve the issues of early diagnosis and management of patients for both dermatologists and other physicians. HIV-associated dermatoses in patients with extracutaneous clinical manifestations of HIV infection have mutually detrimental consequences, which require a uniform interdisciplinary patient management algorithm.