Cooperative work differs depending on contexts and tasks, whether co-located, synchronous, or distributed in time and space. New technology allows new opportunities to support cooperation. A central aspect of cooperation is the relation to individual work; when co-located, people enter and exit cooperation seamlessly. This dissertation explores how technology, situation, and context interplay in various forms of cooperation. It addresses two research questions: (1) How do people get engaged in cooperative work? and (2) How can engagement in distributed cooperative work be supported? The work focuses on ethnographic empirical studies that analyse the interaction between humans and technology across various domains. Workplace studies have been conducted in different fields. Emergency service work, truck driver's work, building maintenance workers, and visitor's technology use at a music festival. The workplace studies in the dissertation imply that field studies are conducted to document and analyse how people use technology and how this use takes place. Common to all studies is the work about activities distributed in time and space. These research findings inform the development of new perspectives, concepts, and design challenges for distributed collaboration. The dissertation discusses two primary ways to engage in cooperative work are identified: requesting and choosing to engage through shared materials and artefacts support awareness and enable cooperative work. The results identify four factors to facilitate engagement in remote cooperative environments: supporting requests and choices to engage, providing opportunities to use artefacts, promoting shareability, and incorporating awareness technology. The dissertation contributes new insights into the interplay between technology, situation, and context in cooperation. Providing design insights for distributed collaboration, and the exploration of design concepts and analysis models. The contributions emphasize the dynamic nature of collaboration and the importance of understanding the relationship between individual and cooperative work to support distributed and remote collaboration effectively.