This study describes the Reflection Connection Cycle professional development designed to support teachers' use and appreciation of students' out-of-school practices related to school mathematics. The year-long program incorporated group lesson design, readings, and video analysis for 14 elementary school (ages 5-12) teachers. Analysis of lesson development, written reflections, and analysis of teacher talk revealed important patterns related to the difficulty in writing lessons that built on students' informal understandings. While initial lessons focused solely on the context of practices like gardening and sports, subsequent lessons show a greater concern for the mathematics in which children were engaged within a practice. A Multi-approach Engagement Framework is presented both as a tool to support further professional development efforts and as a means to describe stability and change in teachers' efforts to connect in-school and out-of-school mathematical understandings.