One promising intervention to support the writing skills of students with and at risk for emotional and behavioral disorders is self-regulated strategy development (SRSD). The purpose of this study was to extend this line of inquiry to a residential setting with teachers serving as interventionists and determine the effects of the SRSD using the STOP and DARE mnemonic for persuasive writing on the writing performance (Correct Word Sequences, Essay Elements, and Essay Quality), and academic engagement of secondary students. In addition, this study extended this line of inquiry by looking at implementation of the intervention only 2 days per week, a lower treatment intensity than previous research has used to find statistically significant gains in writing. Results of a piecewise hierarchical linear model suggest statistically significant gains were made over the course of the intervention in writing and academic engagement when compared to baseline. In addition, student variables such as writing achievement, externalizing/internalizing behavior patterns, age, and attendance predicted writing and engagement. Results of generalization, fidelity, and social validity also are reported.