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Digital transformation has reshaped the organizational and pedagogical dynamics of educational institutions through the expansion of Virtual Learning Environments (VLEs). However, their incorporation often stems from accessibility and technological familiarity rather than strategic decisions. This paper analyzes, through an institutional coupling lens, how different organizational cultures assimilate the implementation of various VLEs and their management implications. The research followed a qualitative-interpretative approach with a comparative multiple case design. The sample, selected through a non-probability purposive and theoretical convenience sampling, consisted of 162 participants (4 directors of technology areas, 8 computer science teachers, and 150 students) from three Argentine institutions: FAUBA (Moodle), ITLM (Chamilo), and ISPJVG (E-ducativa and Google Classroom). The findings demonstrate that VLE effectiveness depends on the alignment between pedagogical design and management decisions, revealing a critical tension between the technological sovereignty of institutional platforms and the operational convenience of global ecosystems. It is concluded that the main contribution of this research lies in operationalizing the category of institutional coupling as an analytical tool for technological governance, allowing educational management to transcend mere instrumental adoption and strategically mediate between data sovereignty and ease of use.