Investigating online child sexual abuse (CSA) crimes is challenging for law enforcement agencies, demanding both digital expertise and knowledge about offences against children while exacting a mental toll on investigators. This article identifies challenges in the investigative process, drawing on audit reports, interviews with police management, observations of meetings, and a workshop with online CSA investigators. The findings reveal difficulties in resource allocation due to varying case sizes and rapid escalation. In addition, while online CSA investigators handle most cases, they require support from other police units; however, a widespread fear of these cases among non-specialized investigators complicates collaborative efforts. Lastly, a culture of organizational “compartmentalization” was described as hindering collaboration, as different branches of investigation remain separated. We discuss how these challenges pose problems to online CSA investigation practices.