The study aimed to identify and understand practices and strategies for enhancing learning through collaboration among a master’s degree in vocational pedagogy (MVP) program, vocational teacher training institutions (VTIs), and workplaces. Using in-depth semi-structured individual and focus group interviews, data were obtained from administrators, mentors, supervisors, students, teachers, officers/managers of the MVP, two VTIs, and four workplaces from central and eastern parts of Uganda. The data analysis was based on Engestrom’s cultural-historical activity theory (CHAT) particularly the concept of expansive learning for resolving contradictions within human activity systems. The findings revealed a need for involving actors in timely planning and disseminating the activity plans, increasing duration for collaborative activities as well as involving the students in the tracking of MVP activity record in fostering the institutional capacity to plan and implement collaborative activities. To strengthen the institutional capacity to supervise learning under collaborative activities, findings indicated a need to engaging workplace mentors and facilitators in learning at the MVP as well as joint supervision and collaborative development of supervision guidelines. To foster the communication between partners, the findings revealed a need to institute a collaboration focal person, providing feedback to collaborating actors and government support on a policy encouraging workplaces’ involvement in vocational training. Relationship issues revealed a need to initiate collaboration based on a signed memorandum of understanding as well as organising workshops and symposiums to equip and orient actors to MVP work methods and practices. Due to contradicting learning cultures and traditions amongst the activity systems, some of the suggested strategies required renegotiating the system especially the university before being implemented to minimise further challenges.