Many models of online student engagement posit a “more is better” relationship between students’ course-related actions and their engagement. However, recent research indicates that the timing of engagement is also an important consideration. In addition to the frequency (how often) of engagement, two other constructs of timing were explored in this study: immediacy (how early) and regularity (in what ordered pattern). These indicators of engagement were applied to three learning assessment types used in an online, undergraduate, competency-based, technology skills course. The study employed advanced data collection and learning analytics techniques to collect continuous behavioral data over seven semesters (n = 438). Results revealed that several indicators of engagement predicted academic success, but significance differed by assessment type. “More” is not always better, as some highly engaged students earn lower grades. Successful students tended to engage earlier with lessons regardless of assessment type.