The cognitive and social demands of collaboration can raise significant motivation challenges. Task progression relies on team members strategically taking control of the problems and adapting accordingly. Theory indicates that productive collaboration involves groups using three modes of regulation: self-regulation, co-regulation, and socially shared regulation. Despite research demonstrating the occurrence of all three modes in collaboration, it is unclear how these modes interact and how co-regulation supports the emergence of self- and shared-regulation of motivation. The study aimed to examine the role co-regulation played in dynamically stimulating the emergence of self- and shared-regulation of motivation. A cross-case comparison was conducted between two groups who experienced high levels of motivation challenges but achieved contrasting perceptions of the overall team learning productivity. During analysis, groups' dynamic regulatory processes within the online environment were visually represented using a tool called the Chronologically-ordered Representation for Tool-Related Activity (CORDTRA). Findings demonstrate that co-regulation of motivation may afford and thwart the emergence of self- and shared-regulation, and these processes interacted with the group's situational challenges and the regulatory skills group members possessed. Comparisons between the two groups indicated that groups' motivation regulation should (a) match the demands of the challenges at hand, (b) be positively supported by group members through co-regulation, and (b) involve a more varied strategic responses so that the group may continue to learn and co-construct knowledge effectively as a team.