With a scarcity of research on multiple working arrangements, the aim of the paper is to contribute empirical data from a Norwegian engineering, procurement, and construction enterprise that shed light on the challenges and benefits of a 14-21 working arrangement in itself and in relation to other working arrangements. We combine a sociotechnical system perspective with systematic content analysis using QSR NVivo, which reveals organizational complexity comprised of indirect, direct, positive, negative, and mutual interplays between various aspects of the enterprise, including processes and outcomes. We find that the 14-21 working arrangement, in combination with other factors of the work system, sets the premises for work processes and outcome factors that are both beneficial and challenging to individuals and the organization. We also find that work process factors, such as work and information flow as well as follow-up and facilitation, depend on the presence of, and dynamic coordination and communication among, individuals across the organization. This in turn requires a support network, work groups, and supervisors to be on the same working arrangement.