Some governments require that educational leaders working in underperforming schools create school improvement plans (SIPs) to guide change efforts. Extant research describes two common approaches to SIPs: (a) a "traditional" approach where leaders create a single plan for an entire academic year, and (b) a "short-cycle" approach where leaders create two plans during an academic year (e.g., one for each semester). Despite widespread appeal, surprisingly little research has been conducted on SIPs and their influence on outcomes of interest. Nearly all studies investigate the traditional approach, and no published studies examine the potential influence of short-cycle SIPs on outcomes of interest (e.g., student achievement). In response to these gaps, the purpose of this study was to explore potential associations between short-cycle SIP quality and student achievement in English/language arts (ELA) and mathematics. We used a publicly available rubric to score 389 short-cycle SIPs on 12 planning domains and then employed a correlational design to examine potential relationships between short-cycle SIP quality and student achievement. Results concluded that short-cycle SIP quality increased over time, but despite small, positive relationships between increased short-cycle SIP quality and increased student achievement, there were no statistically significant impacts. Given the number of factors found to influence student learning, these results are unsurprising, but nevertheless encouraging. We close by discussing how educational leaders might need training to best leverage the short-cycle approach and how future research efforts can continue contributing to a sparse, but growing knowledge base on school improvement planning approaches.