Why do organizations adopt information systems? Is it just because of financial reasons, of concerns for efficiency? Or is it due to external pressures, such as competitor pressure, that an organization adopts an information system? And, how does the adoption take place? Is it a linear process, or is the process one of conflicts? Does a specific person govern this process, or do we have multiple parties involved? What happens if these conflicts occur among those involved? How does the organization move on and achieve a successful information system adoption? By investigating two organizations, one international academic journal and one South American manufacturing company, this thesis aims to investigate the whys and hows of information system adoption, and aims to contribute to the discourse on information system adoptions in small organizations – an often underrepresented segment in information system adoption literature. By adopting different theoretical lenses throughout the five research papers included, this body of work suggests that even when seemingly simple, information system adoptions can become rather complex. The cases reveal that the role of information systems and issues related to information system adoptions are often not well thought-out in the early days of the organization. The actors’ understandings of adoption and consequences mature and the information systems become more intertwined. Common use of stakeholder theory introduces general stakeholders and their interaction with the focal organization. The cases reveal that the adoption process involves multiple actors, even within what would initially appear as a stakeholder, and that those actors can be in conflict with each other. These conflicts often lead to negotiations, and the cases reveal that these negotiations are opportunities of learning; the actors engage with the information system and with each other, gaining new knowledge about the issues at hand. The dissertation argues that there are various social worlds in information system adoptions, and various factors – ranging from organizational structure to social norms – that often affect why and how the organization undergoes an adoption process. The multiple power relations and divergent interests of stakeholders in these adoption processes, and how information systems affect other parts of the organization, reinforce the need for a well thought-out, flexible and reflexive approach to information system adoptions.