Management of chronic disease conditions in the elderly is challenging. They usually have many co-morbidities requiring multiple drug regimens, and memory or cognitive problems that can interfere with management. Also, they sometimes have a degree of social problems as they might often live alone, and thereby cater for their daily activities with minimal assistance. Multiple drug use combined with their fragile health predispose them to adverse drug reactions, drug-drug interactions, and direct drug toxicity from overdosing. We report and discuss the lessons learnt from the case of an elderly woman in an urban setting in sub-Saharan Africa who presented with problems of drug dosing, adverse drug effect, and drug-drug interaction that might prove useful in the future management of hypertension with angiotensin converting enzyme inhibitors.