This case positions the reader as the superintendent of Jefferson City Public Schools (pseudonym). Like many urban school districts in the United States, Jefferson City faces a complex milieu of fiscal challenges attributed to inadequate state funding and declining student enrollment. Within this case, the superintendent must address the failing implementation of a district-wide initiative, which converted K-5 elementary schools to K-8 combination schools in response to declining middle school enrollment. The case invites the reader to consider how the district might engage in strategic planning to revise or eliminate the initiative. The case is appropriate for use in administrator preparation programs, particularly those preparing district-level administrators.