This study was designed to evaluate whether Microsoft Learning Tools is useful for enhancing reading and writing instruction and learning. Four 4th grade and four 6th–12th grade teachers from Bellevue School District in Bellevue, Washington participated. We interviewed them and analyzed reading assessment data to gain an initial understanding of whether the product supported learning. Results indicate overall that Learning Tools appears to be a useful digital tool for supporting not only reading, but also writing and other skills for elementary, middle and high school students, who range from struggling to above grade-level in their skills. Moreover, for struggling readers, Learning Tools “levels the playing field” by supporting access to learning materials beyond their reading skills.