Although the idea of responding to learners' individual needs is far from new in the middle grades movement, there have been renewed efforts in recent years for schools to tailor programs and practices to students' unique interests and needs through "personalized learning" (Bingham, Pane, Steiner, & Hamilton, 2016). To date, little research has examined how teachers experience the enactment of this increasingly popular approach. The purpose of this qualitative case study was to explore the successes and challenges of 1 middle school teaching team during its first year enacting a teamwide personalized learning class called E-Time. Findings indicated that teachers perceived the primary success of E-Time to be its contribution to stronger relationships with and among their students. The main challenge teachers experienced was structuring the learning environment, including transferring control of learning objectives to students, establishing deadlines, and developing clear expectations for the quality and outcomes of student work. The aspects of the class that contributed to these challenges included relinquishing control over key classroom activities, the multiplicity of student projects, and a misalignment between teachers' core classroom practices and those required in E-Time. Overall, findings suggest that personalized learning may represent a substantial shift in practice for many middle grades teachers given the heavy reliance on direct instruction in many middle schools (McEwin & Greene, 2011). Findings are used to identify potential areas for professional development to support middle grades educators in the transition to personalized learning, including scaffolding student-directed learning, facilitating and managing diverse student projects, and individualizing student assessment.