In review of assessment and grading systems, there is often discord regarding best practice to foster student learning. Problems and disconnect between assessment and learning were identified as the area of focus of this study, more specifically examining the usage of student self-assessment as an effective gauge for learning and instruction, in addition to assessment. The team has focused the research on the perceptions of student self-assessment knowledge, training, and application by building level administrators in order to formulate recommendations for implementation. Guiding questions based upon background research fit into four main categories: research-supported criteria that define effective student self-assessment, are schools implementing the criteria to achieve high-fidelity student self-assessment, are schools valuing the importance of student self-assessment in the education of their students across grade levels and content areas, and perceived barriers to successful implementation of student self-assessment. A survey was conducted, focused on these areas to gather information from current building level administrators in Missouri public schools in fall of 2020. Information was collected regarding the level of resources districts allocated to student self-assessment, student and teacher familiarity with self-assessment practices, teacher usage of self-assessment in the classroom, and knowledge of building level administrators regarding self-assessment. Based upon data accumulated through the survey, researchers devised four recommendations based upon patterns and trends within the responses regarding this practice, in conjunction with previous background research. Recommendations suggested: include provisions and resources to shift culture in buildings for implementation of SSA, focus resources to assist integration of this skill into personal professional practice, creation of an educational environment in which best practice in student self-assessment can be supported and full inclusion of student self-assessment in a school district after previous recommendations have been satisfied. Recommended further research proposes analyzing teacher perception of SSA specifically, researching the barriers to implementation of this practice in more depth, and conducting the study again at a later date following the COVID-19 pandemic. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]