The authors conducted two studies as part of a federally funded project to improve the writing performance of students identified as at risk for behavioral difficulties and struggling with writing. One study focused on improving persuasive writing abilities, whereas the second study focused on improving story writing abilities. Many of the students they worked with needed accommodations or modifications to the Self-Regulated Strategies Development (SRSD) approach. As Tomlinson (1999) noted, instruction can be differentiated or modified for students in three different areas: (1) content; (2) process; or (3) products. Content can be differentiated two ways: (1) by adjusting the materials the teacher uses with the student; or (2) by amending what the teacher wants the student to learn. Process involves meeting the learning needs of the student through different activities. Product involves students demonstrating their learning in ways that reflect their abilities. In this article, the authors present the cases of Ben, Cory, and Mara, students who presented unique challenges that needed to be addressed in order for them to develop powerful writing and self-regulation strategies that made a real difference in their writing. These students attended an elementary school in the Southeast that implemented schoolwide Positive Behavioral Support (PBS). The intent of PBS is to prevent and respond to problem behaviors by instituting a three-tiered model of prevention that begins with an instructional approach to behavior. The authors discuss how instruction in the SRSD approach and writing strategies can be differentiated within a PBS approach for second-grade students in need of additional supports. (Contains 4 figures.)