This paper addresses how the increased use of digital documentation systems in specialized housing units alter and create new kinds of documentation practices within the realm of pedagogical and social workers. The paper is based on a two-year comprehensive field study at five different specialised housing units for various kinds of disabled people. Three distinct consequences of the increased use of digital documentation is identified throughout the paper, first; a decoupling between documentation and pedagogical practice, second; new divisions of labor and third; creating an experienced paradox between documenting ‘everything’ and ‘nothing’ at the same time. We discuss these consequences in light of organizational learning theory, and discuss potential understandings that can be drawn in regard to the field of pedagogical practice in social work and insight into the dynamics between digital documentation systems and everyday practices.