Gateway courses in English challenge students to strengthen skills in critical thinking, reading, grammar, and writing structure and strategies -- skills that also help build competency in comprehension and composition. They can also prove to be a particular challenge to many community college students. This case study examines the efforts at three of the seven Achieving the Dream (ATD) Network colleges participating in the Every Learner Everywhere (Every Learner) initiative that focused on English courses as part of their efforts to implement adaptive courseware into gateway courses to help more students persist and succeed. The study suggests that adaptive courseware helped students make connections between mastering discrete skills and their overall progress in writing, particularly when intentionally integrated into class activities.