Principals are responsible for planning school improvement efforts at the school level to leverage increases in student achievement. Recent research underscores how principals engage in satisficing behaviors that result in low-quality school improvement plans (SIPs). To disrupt compliance-based planning practices and produce high-quality SIPs, some districts have shifted from yearlong planning to short-cycle planning. Districts need to establish a coherent understanding of improvement planning to motivate and sustain new principal planning practices. Through the coherence framework, this qualitative study explored one large urban district's shift from yearlong planning processes to short-cycle planning processes to understand principals' perspectives on improvement planning and the potential shift to short-cycle planning. Researchers examined eight principals' short-cycle plans. Principals who participated in a two-year partnership with a University System Leadership Program (USLP) for school-level support for school improvement were interviewed. Principal interviews, USLP site lead feedback, and principal supervisors' interview data to triangulate the short-cycle plans. Data analysis revealed the existence of a perverse coherence that impeded principals' shift to short-cycle planning. Findings suggest that districts examine their internal practices and processes influencing principals' improvement planning practices and attend to principals' understanding and practice of improvement planning by providing continuous professional learning and feedback.