Tobacco control advocates have played an important role in Ontario's tobacco control efforts. As with other advocacy work, their efforts have been mostly unexamined. Based on Ontario's tobacco control advocacy work, this article highlights the challenges of evaluating the work of advocates (e.g., having multiple aims, multilayered structures, shifting time frames, measuring longterm goals, dealing with external factors, having goals change at midstream, having different approaches working simultaneously) and summarizes some theories and tools (e.g., Bellwether Methodology, Agenda Setting Theory, Context-in approaches, Pathways of Influence, and logic models) that have been used to conduct effective advocacy evaluations.