This was a case study of the principal succession planning practices of a large school district in Oregon. For the study, the researcher interviewed nine principals and nine central office administrators and surveyed 17, K-12 assistant principals within the studied school district. The findings from this study reveal many strengths and weaknesses within the studied district's current principal succession planning practices and is followed by considerations for this school district that might be applied to other school districts. The considerations include creating clarity around the desired qualities and skills of an effective principal, creating more teacher leader pathways to principalships, aligning current practices for the district's aspiring administrators to their partner university's administrator licensure program, and intentionally supporting assistant principals and principals through mentoring and focused professional development. [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.]