As a change in a setting displaying scarcity of resources, plurality of choices and technological change, Digital Transformation implies paradoxes of change. Following this, we wonder how paradoxes and Digital Transformation interact and unfold. We investigate the case of a records management company engaging with digitizing and digitalizing of their offers. We implement 23 hours of semi-directive interviews, two site visits and written sources analyses that we code thematically. We find that paradoxes of Digital Transformation can be managed leveraging specificities of digital technologies. Organizing and performing paradoxes are addressed through temporal and geographical splitting strategies, relying on external and internal skills, before developing the resources to hire. National-level reflection complements the strategy. Performing is demonstrated via expertise-oriented online and offline communication supports. The paradox of belonging, fuelled by splitting strategies is the most difficult to manage, addressed through reframing discourses, posters representing the human stories behind the file and expertise-raising actions. On the basis of these dynamics, we suggest an exploratory model.