Principals' decisions play an important part in determining whether or not teachers are offered contracts, and school principals face prominent challenges that predictably work against recommending contract non-renewal for teachers. Some of the commonly identified challenges include time, teacher unions, and laws protecting teachers (Nixon, Packard, & Dam, 201 la; Nixon, Packard, & Dam, 2011b; Painter, 2000). Learning more about the criteria that principals apply to teacher contract non-renewal decisions affords an opportunity to improve the teacher preparation process and in-service teacher professional development. This line of inquiry also assists the identification of themes for principal development. Further, identifying barriers that hinder principals from addressing ineffective teachers serves to improve the prospect of learning for students. It is unclear if principals have all the tools that they need to work toward having an effective teacher in every classroom, and recent reforms to teacher evaluation processes make it more dubious. This quantitative study investigated reasons for the contract non-renewal of probationary teachers and the obstacles that school principals face in dealing with ineffective teachers. School principals in Colorado, Idaho, Montana, and Utah provided demographic information and reasons they would be likely to recommend contract non-renewal for probationary teachers. Findings from these four states, representing the Rocky Mountain region are addressed in this paper.