Increased expectations for writing performance have created a need for formative writing assessments that will help middle school teachers better understand adolescents' gradeappropriate writing skills and monitor the progress of students with or at risk for writing disabilities. In this practice piece, we first explain research-based recommendations for highquality writing prompts that are interesting to students, provide clear directions, and ensure accessibility and fairness. Then, we use lessons learned from working with adolescents in Tier 2 literacy intervention classes to demonstrate how teachers can apply the recommendations to identify or develop prompts that will encourage students to write responses. In addition, we explain how analytic rubrics may be used to evaluate responses as a means of informing instruction and further refining the prompts.Standardized writing assessments have become an established facet of today's educational system (Olinghouse & Colwell, 2013). After repeated calls for greater attention to writing in the literacy curriculum to better prepare adolescents for their future educational and occupational endeavors (Graham & Perin, 2007), states have been adopting more rigorous writing standards as well as accountability assessments in recent years (Shanahan, 2015). Rather than the formulaic five-paragraph essay that would have been considered proficient a couple of decades ago, current standards require middle school students to demonstrate expressive writing that is complex in both content and structure (Campbell & Latimer, 2012). Thus, there is a need for formative writing assessments to help teachers identify and plan Tier 2 interventions for students at risk of not meeting the more rigorous on-grade-level expectations.