Half of people with human immunodeficiency virus (HIV) have HIV-associated neurocognitive disorder (HAND). Fortunately, cognitive training programs can improve function across cognitive domains, which may translate to everyday functioning. The Training on Purpose (TOPS) Study was designed to reverse HAND by targeting cognitive training to specific cognitive impairments that contributed to the diagnosis. A secondary aim of TOPS was to determine whether such cognitive training improved subjective and objective everyday functioning. In this two-group pre–post experimental design study, 109 adults with HAND were randomized to either: (1) a no-contact control group (no training) or (2) the Individualized-Targeted Cognitive Training group. Each participant received approximately 10 hours of cognitive training in two selected cognitive domains based on her/his individual baseline cognitive performance. Thus, 20 hours of individualized training on these two cognitive domains occurred over a course of 12 weeks in 1–2 hour sessions. Specific to the secondary aim of TOPS, measures of everyday functioning were administered before and after cognitive training to examine transfer effects. The analyses revealed that in general, speed of processing training produced benefits in everyday functioning as measured by the medication adherence visual analogue scale and the Timed Instrumental Activities of Daily Living test. Inconsistent findings were found for the other seven cognitive training protocols in either improving everyday functioning or reducing perceived everyday functioning; however, there may be other contributing factors that obscured such effects needing further research. This study demonstrated that some training protocols vary in efficacy in altering both objective and subjective everyday functioning ability.