The purpose of this study was to examine the transition experience that students make by moving from a Montessori environment to a traditional educational setting. This study examined this transition through the perspective of the teacher. The backgrounds of the teachers interviewed included: 8th grade Montessori teachers, 9th grade teachers from each core subject area, a district Montessori coordinator, and a Montessori teacher trainer. The author used a qualitative approach in order to examine the underlying details of this experience. The conversations with the teachers revealed that this is a relatively smooth transition for Montessori students to make. Although the transition experience was successful, there were a few obstacles discovered that should be addressed. This study offers some recommendations to assist in eliminating these barriers. One limitation of this study is that it describes the transition experience from one small rural school district. However, it is believed that the results can be generalized to describe this transition in similar settings. With a limited number of Montessori high schools, this topic is deserving of further exploration.