This paper explores timelines as a web-based tool for collaboration between citizens and municipal caseworkers. The paper takes its outset in a case study of planning and control of parental leave; a process that may involve surprisingly many actors. As part of the case study, a web-based timeline, CaseLine, was designed. This design crosses the boundaries between leisure and work, in ways that are different from what is often seen in current HCI. The timeline has several roles on these boundaries: It is a shared planning and visualization tool that may be used by parents and caseworkers alone or together, it serves as a contract and a sandbox, as a record and a plan, as inspiration for planning and an authoritative road, as a common information space and a fragmented exchange. Serving all these roles does not happen smoothly, and the paper discusses the challenges of such timeline interaction in, and beyond this case.