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There has been increasing enthusiasm for the use of continuous improvement (CI) methods to improve school systems. These methods are designed to better grapple with some of the uncertainties of the field of education, but little research to date has directly explored how uncertainty influences educators’ use of CI. This paper addresses that gap by developing a typology of three kinds of uncertainty (technical, representational, and environmental) that influence organizational improvement efforts, and uses that typology as a conceptual lens to investigate how educators in two districts respond to a system-wide CI initiative. It finds that this CI initiative adeptly manages some forms of uncertainty, but underestimates or is inattentive to other forms of uncertainty, often with problematic consequences.