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Although patient-controlled analgesia (PCA) is considered the standard in postoperative pain control, research examining PCA use among cognitively impaired older adults is lacking. The authors reviewed a case series of 10 adults aged 65 years and older admitted to the geriatrics or orthopedic services of an urban tertiary care center in New York City with acute pain and cognitive impairment or dementia who were administered PCA. Four patients from this cohort are presented in detail, demonstrating the challenges of PCA use in this population. A series of clinical pearls follows each case, outlining strategies for improving pain management. The authors’ findings suggest that cognitive evaluations limited to alertness and orientation and failure to perform functional assessments may hinder the identification of patients who are poor candidates for PCA. Once PCA has been initiated, clinicians must regularly review device use and document cognitive function and pain score patterns to identify PCA underuse or misuse. Finally, rapid fluctuations in cognitive or functional status may require adoption of a more flexible pain management strategy. Despite these challenges, a subset of cognitively impaired older adults can successfully understand and operate PCA devices. Additional research is needed to (1) develop screening tools for identifying and monitoring older adults who may benefit from PCA and (2) create innovative approaches for improving pain management in the cognitively impaired.