We report from the initial steps of a collaboration project between two post-doctoral projects, both using a qualitative action research approach to address challenges related to shifting from a free text to a structured EPR system constituting important preconditions for establishing advanced decision support and reuse of healthcare data. We have started to explore three areas that may influence this process related to: 1) Legislative challenges of getting access to all relevant healthcare data. 2) Challenges of exchanging data between silo systems and open platform systems. 3) Replacing a free text silo EPR with an open platform system – and the practical challenges of defining the content of the context sensitive structured EPR. Hence, we ask the following research questions: How to address challenges related to the shift from free text to structured EPR systems? How will the need for semantic interoperability between different EPRs influence the goal of advanced clinical decision support? Empirically, we draw on the regional FRESK program (2017–2022), in the North Norwegian Health Region, which includes implementing both a new regional open platform based EPR system, and a proprietary medical chart system.