Background/Context Tensions between university-based teacher preparation courses and field placements have long been identified as an obstacle to novices’ uptake of promising instructional practices. This tension is particularly salient for writing instruction, which continues to receive inadequate attention in K–12 classrooms. More scholarship is needed to develop a theory and practice of methods education that accounts for these tensions. Purpose This study investigated how opportunities to learn to teach writing in preservice preparation mediated teacher candidates’ learning. The investigation's aim was to add to our knowledge of how teachers learn and the factors that impact this learning to offer implications for improving teacher education. Participants and Settings Participants included literacy methods course instructors from two post-baccalaureate, university-based, K–8 teacher certification programs and participating candidates enrolled in these courses (N = 20). Settings included methods course meetings and participating candidates’ field placements. Research Design This comparative case study examined opportunities to learn and preservice teachers’ uptake of pedagogical tools across two programs. A cultural–historical theoretical lens helped to identify consequential differences in the nature of activity in preservice teachers’ methods courses and field placement experiences. Data included instructor interviews, methods course observations, teacher candidate focus groups, and field placement observations. Patterns of field and course activity in each program were identified and linked to patterns of appropriation within and across the two cohorts. Findings In one program, methods course activity included opportunities to make sense of the approaches to teaching writing that teacher candidates encountered across past and current experiences. The instructor leveraged points of tension and alignment across settings, prompting teacher candidates to consider affordances and variations of pedagogical tools for particular contexts and goals. This permeable setting supported candidates to develop habits of thinking about pedagogical tools, habits that facilitated uptake of integrated instructional frameworks. In the other program, methods activity focused almost exclusively on the tools and tasks presented in that setting. This circumscribed approach did not support sense-making across settings, which was refected in the fragmented nature of teacher candidates’ pedagogical tool uptake. Conclusions Findings challenge the notion that contradictions in teacher education are necessarily problematic, suggesting instead that they might be leveraged as entry points for sense-making. In addition, permeability is identified as a useful design principle for supporting learning across settings. Finally, a framework of pedagogical tools for subject-matter teaching may provide novices with a strong starting point for teaching and a scaffold for further learning. “I felt at the beginning of the school year that writing was not going to be a strong point for me…. Maybe part of it was the way [my cooperating teacher] modeled it for me; it was just free flowing, kind of … jumping from thing to thing [each day]…. It wasn't like the way [our methods instructor] had modeled for us … [using] four-week units.” –Sheri, teacher candidate, Madrona University