Expressive writing is important for school and life success, but remains challenging for many students with emotional and behavioral disabilities. Emerging evidence reveals promise for teaching students with learning and behavioral issues to improve written expression with self-regulated strategy development instruction. In that research, students are taught to criterion performance (e.g., demonstrating mastery performance for each lesson) for instructional periods sometimes as long as 50 days (see Mastropieri et al., 2009). What is unknown, however, is given the more limited time constraints within a school setting, whether students with emotional disabilities, many with comorbidity, can successfully improve within a school's allocated time for teaching persuasive essays. The current study used a waitlist comparison condition and randomly assigned 32 eighth graders to either an immediate intervention or a waitlist delayed intervention condition during which an organizational and planning strategy for writing persuasive essays was taught. Findings revealed students were able to successfully learn and apply the strategy within a reduced time period as evidenced by statistically significant higher quality essays that contained more essay elements, words, sentences, and transition words. Student interviews revealed positive attitudes toward instruction and strategy use. Two months following posttesting, surprise maintenance measures were administered that yielded equivocal results suggesting periodic review sessions may be appropriate. Implications for the classroom practice are discussed.