The first steps that new teachers take in their classrooms lead them down a path that presents many challenges, and these challenges are the reason that beginning teachers are a vulnerable population in the context of educational practitioners. This autoethnography examines two new teachers as they transition from their teacher education programs to teaching in the classroom. This research frames their experiences using the perspective of self-determination theory to characterize the psychological nature of beginning teachers' challenges as they transition into a community of educational practice. Participants reported how they perceived feeling ill-prepared for the realities of classrooms and provide ideas on what desired changes in teacher education might look like. The novel contribution of this study highlights intervention sites for alleviating the unique vulnerability of the newest teachers as they make a difficult transition from practice teaching to teaching practice.