Despite a growing recognition of the significance of student transportation for promoting equitable school choice, to date, there has been limited understanding of the implementation of school transportation policies, particularly in choice-heavy settings. Moreover, little is known about the challenges associated with managing student transportation in large school districts or how school and district administrators working in distinct contexts respond to these challenges. This brief draws on interview data collected from district administrators, charter school leaders, charter authorizers, and stakeholders in three choice-rich school districts with distinct transportation policies and public transit infrastructures—Detroit, New Orleans, and New York City—to identify the common challenges associated with implementing student transportation policies and administrators’ responses to them. The brief includes a discussion of the implications of high transportation costs, logistical complexity, and student safety challenges as well as non-uniform transportation provision and transportation policies for equitable access to charter schools. It ends with a review of some potential policy alternatives that policymakers should consider when designing transportation policies or working to improve existing transportation practices.