Implementing school choice programs and bolstering parental engagement are both frequently touted as critical steps in improving educational outcomes in US schools. Many policy makers contend that by providing parents with more schooling options for their children, parents will become more involved in their children's education, resulting in better and more equitable opportunities. The authors consider whether more school choices necessarily translate into more robust parental involvement, by chronicling for 5 years both the opportunities for and barriers to engagement that parents encountered in the Clarksville School District as it underwent a significant period of reform. The authors conclude that school choice does not always have a positive impact on parental engagement, and engagement in turn does not always translate into better or more equitable opportunities. In some cases, increased choice may present additional challenges to parents as they struggle to find accurate information, weigh a variety of problematic options, and consider the impact of their personal decisions on their children and on the overall well-being of the district.