This study explored elementary and secondary school administrators’ perspectives on their attempts to build assessment literacy—an understanding of the principles and practices of sound assessment. Using a semistructured interview format, administrators were asked to share successes and challenges with various types of assessment. Transcripts revealed an imbalance between formative and summative assessment practices and a variety of attitudinal, structural and resource factors that constrain administrators’ ability to foster changes that align with recent assessment research. The implications of the findings are discussed in relation to instructional leadership, capacity building and educational reform.