Despite the increasing availability of human immunodeficiency virus (HIV) testing and emphasis on routine HIV testing, many individuals develop advanced acquired immunodeficiency syndrome (AIDS) and often present to care with an opportunistic infection as the sentinel event. Whereas concurrent opportunistic infections may occur, coexisting Pneumocystis jiroveci pneumonia and disseminated cryptococcosis with cryptococcal pneumonia as an initial presentation of undiagnosed AIDS is uncommon. Human immunodeficiency virus testing is indicated when an individual presents with an opportunistic infection without a known HIV infection diagnosis. Given the wide availability and convenience of rapid testing, individuals may be tested with an oral rapid HIV assay, which can yield false-negatives, even in advanced HIV disease. We present the case of a man with undiagnosed AIDS who presents with concurrent P. jiroveci pneumonia and cryptococcosis and 2 false-negative oral rapid HIV test results.