Procrastination can theoretically be conceived of as a motivational selfregulatory failure and is assumed to be a risk factor of college dropout in the higher education context. It was hypothesized that students' procrastination and college dropout intentions are closely related with their motivational regulation-in terms of the effectiveness of their efforts to self-regulate their motivation and in terms of the strategic knowledge behind the actual regulation attempts (conditional knowledge about the suitability of different motivational regulation strategies in different motivational problem situations). Data from 515 college students, who participated in an online study and stem from a variety of fields of study (58% female; average age of 23.2 years), was analyzed to test the hypothesized relationships. Structural equation modeling indicated that conditional motivational regulation strategy knowledge was positively linked to the effectiveness of motivational regulation, which in turn was negatively linked to academic procrastination and college dropout intentions. Subsequently, academic procrastination was positively related with college dropout intentions. A total negative indirect effect of conditional strategy knowledge on college dropout intentions was mediated by effectiveness of regulation and academic procrastination. The results are in line with the assumption that good competences to regulate one's own motivation are an important protection factor against academic procrastination and college dropout.