In this qualitative case study, we explored student and teachers' experiences with the implementation of personalized learning in a rural Kentucky school district. Students revealed differences among teachers implementing personalized learning. Student engagement depended on their teachers' willingness to adapt their instruction and learning environments for personalized learning. Teachers noted the need to release some of the control they have traditionally had and turn those responsibilities, to a degree, over to students. We also identified a need for teachers to have more training and support while transitioning to personalized learning; not only challenging them to change their mindset, but also on the level of work required in lesson planning and monitoring student progress in personalized learning. The implementation of personalized learning requires a collaborative process in which all stakeholders have an opportunity to understand the complexity of the personalized learning framework and what it needs for implementation. This requires working to develop a consistent definition of the personalized learning model implemented so that training, resources, and support can be determined prior to implementation.