The implementation of the No Child Left Behind (NCLB) Act in 2002 has increased the emphasis on standardized achievement tests. Principals are asked to lead instruction and improve student achievement through assessment. NCLB has sanctions that could include replacing a school principal. The purpose of this study was to look at the level of assessment literacy of high school principals in the state of Montana. An email was sent to all practicing high school principals (N = 169) inviting them to participate in a survey. The survey asked demographic questions regarding years in the classroom, years as principal, overall education, size of school population, and region. The survey was also designed to test their level of assessment literacy using the Classroom Assessment Literacy Inventory (CALI) as used in similar studies. The principals that completed the survey were also asked to have two teachers of English, science, or math take the same CALI. A total of 32 principals and 14 teachers completed the survey. The responses indicated that the level of teacher assessment literacy closely mirrored the results from studies conducted in 1993 and 2003 using the CALI. The results from the principals' participation showed lower scores in all but one area of the Standards for Teacher Competence on Educational Assessment of Students. The overall score by principals on the CALI was 59% correct in comparison with the teachers' overall score of just under 63%. Findings included the level of teacher scores on the CALI have not changed significantly in over twenty years. In an era of increased use of assessment, principal scores are lower than that of classroom teachers. The study was conducted in one state of a rural nature when compared to populations nationwide. The results are discussed in terms of use to establish a baseline that can be used in further study of assessment literacy of both classroom teachers and principals in the state of Montana. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]