School calendar decisions in rural districts are shaped by staffing challenges, financial pressures, and community needs, yet research on the four-day school week (4DSW) has focused primarily on student achievement. This cross-sectional study used parallel surveys of Missouri principals—94 in 4DSW districts and 70 in five-day school week (5DSW) districts, to examine principals’ self-reported perceptions of schedule-related motivations, professional time use, and stakeholder satisfaction. In Missouri, 192 of the state’s 516 public school districts—about 37%, almost all of them rural, operated on a four-day calendar in 2026–2027, up from 34 in 2018–2019. Mann–Whitney U analyses indicated that principals in 4DSW districts more often rated teacher recruitment and retention, operating costs, and family scheduling as important considerations, whereas principals in 5DSW districts placed greater emphasis on student recruitment and academic performance; several of these differences were attenuated after correction for multiple comparisons. Principals in 4DSW districts also reported more weekly time devoted to professional development, planning, and mentoring, with the fifth day frequently used for adult collaboration. No statistically significant differences were detected between groups in the proportion of principals reporting any weekly time for services to English Learners, gifted and talented students, or students receiving special education. Principals in 4DSW districts reported consistently high perceived satisfaction with the schedule. Because the design is cross-sectional and all measures reflect principal reports, the findings describe associations rather than effects of the calendar. The results suggest that rural districts often view the 4DSW through a broader organizational and workforce lens than achievement-focused research typically reflects.