This work reports the findings of a study about the complex relationship between the production of educational video, its integration within an academic setting and the actual use that its target audience makes of it. A series of studies were conducted within the higher education context, in which mixed methods and instruments were employed to gather evidence from the experiences of the main stakeholders. The five themes that were identified as crucial for successfully producing and integrating video in academic settings are: overcoming technological barriers; student-centred and student controlled content; institutional support; integration of the video enriched learning activity; and the educator's and students' involvement in the conception of the video enriched learning activity. Analyses and findings of this work led to think that the key for producing effective video enriched learning activities lies within the relationship between content and context and is greatly influenced by the roles played by the stakeholders: the producers or video creators; the educators or video users; and the students or video beneficiaries.