Issues of non-use of available health information technology (HIT) have been referred to as the ‘last mile problem’ impeding harnessing the full potential of HIT. We reflect upon which competencies are needed to address the last mile problem by ensuring a context-sensitive implementation. We argue that there is a need for context-sensitive digital integrators, who can navigate the realm where technological systems meet practice. This entails a situated, socio-technical, context-sensitive approach and competencies which are not easily addressed through formal training but require lifelong situated learning, as the field evolves continuously. Our ambition is to highlight the complexities of implementation and integration into local practice. This paper emphasizes the role of digital integrators in the hope of fostering further discussions on how to acknowledge and nourish these competencies in order to address and go beyond the last mile problem.