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The purpose of this instrumental case study was to explore the experiences of resident teachers and mentor teachers who participated in the inaugural year of a teacher residency program to strengthen the program design. As this model gains traction across the United States, it is important to consider the benefits and challenges of participating in a teacher residency program, so these programs can be more effective in training and retaining new teachers. Five resident teachers and five mentor teachers shared their experiences, noting the time in the classroom as the overall benefit, but lack of university communication, misalignment of coursework, and compensation schedules as challenges. Insights into the need for more intentional communication and thoughtful planning are shared.