This article attempts to answer the questions: What are the challenges, problems and obstacles of involving less self-motivated students in MOOCs and how do they relate to their learning connectivism? The correlations between connectivism and contextualized learning through a formative experience of the Open Educational Movement was analyzed in order to propose strategies that result in greater perseverance, active participation and retention of less self-motivated students in MOOCs. A mixed method approach was used to survey students, interview students and coordinators, and analyze relevant documents. The findings were classified as (1) Challenges: self-motivation, self-regulation abilities, extra time invested, release requirements, goals and inductive activities before the course opening, unsatisfactory identification of students, difficult activities, feedback monitoring and a platform incompatible with balancing its use with that of social networks; (2) Problems: limited information and communication technology skills, difficult feedback research in forums, uncertain peer feedback when not theory-based or scaffolded by teachers, scarce theoretical support in evidence portfolios and a lack of means to help low self-motivated or self-regulated students; (3) Main contextual obstacles: some students cannot count on their employers’ support or continuous technology access, some students basic wellbeing needs are not met, and inability to contextualize learning; (4) Connectivism: students’ motivation in the MOOC content and their expanding knowledge networks. Based on these findings, a MOOC design requirement template aimed at supporting students’ self-motivation and self-regulation through connectivism is provided.