Learning to operate in technology-driven working modes is topical in many organisations today due to the COVID-19 pandemic crisis. The pandemic has forced especially knowledge-work organisations to quickly shift to remote or hybrid working modes, where all or some of the staff are operating and collaborating via digital tools. The aim of this qualitative case study is to explore and explicate a learning story of an organisation within the public sector transitioning quickly to a technology-driven hybrid working mode during the crisis. As findings, the paper presents the identified immediate and evolving facilitators that point to the organisation’s learning to develop capabilities for operating effectively in the enforced and volatile conditions. Additionally, the potential long-term organisational development effects stemming from the situation are considered. In the findings, social aspects of work, such as open communication, collaboration, and awareness gained emphasis, while digital technology is one of the ground enablers. We apply a frame of dynamic capabilities together with workplace learning and aim to provide new insights into their development processes with a cross-organisational approach. In terms of practical implications, we suggest new understandings for the management on how organisations may learn and fare under uncertainty, volatility, and transitioning to digital collaboration.