Middle school learners with disabilities, particularly learning disabilities, struggle with organizing their thoughts, expressing their ideas, spelling, the use of content vocabulary, the mechanics of writing, fluency, and overall, the primary elements of written expression (Graham et al., 2015). While writing complicates learning for students with disabilities across the K--12 environment, middle school years are particularly problematic. McMaster and colleagues (2020) suggested bimonthly 3-minute progress monitoring (PM) assessments are required to achieve teacher understanding of student need and align the respective instructional practice (McKeown et al., 2019). The purpose of this article is to introduce a technology-supported PM tool that offers periodic formative feedback on student writing. Developed to be used FtF and across the continuum of various online, hybrid, and virtual learning environments, the progress monitoring tool assesses middle school students, specifically those identified with writing challenges.