This article describes key challenges experienced and addressed during the evaluation of the Government of Alberta's 10-Year Fetal Alcohol Spectrum Disorder (FASD) Strategic Plan (2007–2017). The purpose was to understand how the strategic plan was progressing toward outcomes at the fifth year of its implementation. Following a description of the system change initiative and evaluation context, an account of key challenges for one outcome is presented, including attempts to address and the effects on the evaluation. The implications for evaluation practice focused on encouraging evaluation participation and enhancing usefulness of data highlight the need for infrastructure to support evaluation of system change initiatives.