This article presents three in-depth case studies focused on supporting students with learning challenges to learn math strategically. Participants were three eighth-grade students enrolled in a learning assistance classroom who were of at least average intelligence but who were performing significantly below grade level in mathematics. These case studies document the processes by which these students were supported to self-regulate their learning in mathematics more effectively. We begin by outlining important instructional foci in mathematics education for intermediate or secondary students with learning disabilities, along with what research indicates are effective instructional processes. In that context, we introduce the theoretical principles underlying the instructional model used here -- Strategic Content Learning (SCL). Based on analyses of case study data, we describe how SCL instruction was structured to promote strategic learning. Throughout the discussion, intervention processes are described in sufficient detail to be of use to practitioners.