This paper explores the role of learning technology professionals (LTPs) in supporting a Higher Education institution (HEI) that is migrating from one virtual learning environment (VLE) to another, through interviewing five participants to generate an in-depth study. The literature underpins the central thesis of this paper positing that the complexities of VLE migration, combined with ambiguous role definitions and unclear transition protocols, affect LTPs’ ability to support institutional change. This project was driven by a desire to understand how best to support the use of a VLE when change is being thrust on its users. Activity-Oriented Design Method (AODM) was used to generate open-ended interview questions investigating possible contradictions that emerge specifically during the VLE migration process, and then the interview transcripts were analysed using to explore tensions within and between elements of the migration activity. Analysis through Activity Theory (AT) revealed that key challenges during the transition stemmed not from technological issues, but from unclear regulations, policies, and expectations surrounding the migration process. Particular tensions emerged round the division of labour and tool requirements during the transition period. This research contributes to the growing body of literature on managing VLE migrations, offering practical insights for other HEIs planning similar platform transformations. Future research could explore the broader implications of these findings across related activity systems involved in educational technology transitions.