This practice report examines the results of inserting program-specific, contextualised modules and instructors into an online student success course in a two-year college environment. The results of multiple semesters of pre-contextualised instruction (Northern Hemisphere Spring and Fall 2015) and post-contextualisation instruction (Northern Hemisphere Fall 2016 and Spring 2017), showed an increase in next semester retention. Additionally, ten student success course instructors were interviewed to determine critical elements of the course. Instructors revealed that time management, stress management, and program-specific assignments were the most beneficial components of the course.