Learning Expectations and Academic Preparation (LEAP) was a two-year pilot offering a cohort (20 students) of our lowest scoring English and mathematics developmental students an intensive cross-disciplinary semester to accelerate through their developmental courses. Blending learning community and summer bridge best practices, LEAP incorporated significant scaffolding to help students develop transferable cognitive, academic, and college skills. In both pilot semesters, we achieved early successes; however, our retention/success rates over time tended to match rather than substantially exceed that of traditional courses. While LEAP did not achieve long-term sustainability, we reflect in this article on our "take-aways" as individual instructors, developmental program coordinators, and faculty members promoting stronger academic and college skills on a university-wide level.