As students’ achievement is correlated with self-regulation, finding interventions promoting self-regulated learning (SRL) in online courses is a current focus of research. However, few studies have explored the potential of contract learning in scaffolding and developing SRL in non-traditional learners who have work and family and are at risk of dropout. Here, we investigate the utility of contract learning using a qualitative approach. Using a qualitative approach, we collected data from the experience of one teacher and seven non-traditional learners in an online English for Specific Purposes (ESP) course. The data were collected from teacher logs over eight months and semi-structured interviews with the students. The results of deductive thematic analysis of the data indicate that contract learning positively affected the forethought, performance, and self-reflection phases. Further, despite the cognitive, emotional, external, motivational, and behavioral challenges aggravated by the pandemic, the teacher’s efforts to implement contract learning affected the persistence and effort, goal setting, strategic planning, and time management of most learners (N = 4). Possible reasons for the learners’ success and failure and the implications for developing SRL skills in students at risk of dropout in online English courses are discussed.