We explore key lessons arising out of target-setting agendas in tobacco control. Two real-world examples are described that illustrate the pitfalls of choosing an omnibus target for a comprehensive strategy: (a) a target to reduce wholesale cigarette sales in Ontario and (b) a First Ministers' target to reduce current smoking. Changing contexts brought about by shifts in illicit tobacco sales made it problematic to interpret success in both cases. The discussion draws attention to key considerations in setting targets, including unintended consequences, data quality, ideal number, and the importance of context such as stakeholder roles in target selection and reporting.