This paper examines caseworkers' efforts to plan and find appropriate interventions for troublesome young people. Strauss's concept of trajectory is applied to analyse how Swedish caseworkers shape and manage the evolving care trajectories using assessments for young people in secure accommodation, i.e. institutional youth assessments. The empirical material consists of surveys to 82 caseworkers concerning 85 institutional youth assessments and interviews with 16 of these caseworkers. The findings reveal ongoing care trajectories that are out of control where the assessments are seen as an opportunity of change for the youths. Diagnoses, confirmations and plans for action are provided through the assessments and used by the caseworkers in negotiations for resources. Three orientations of contributions to the caseworkers' management of care trajectories were found, all reflecting the many uncertainties of child welfare work: child centred, professional and discharge of liability. In conclusion, the caseworkers searched for the right measures to manage change and achieve youth compliance, but it was also a matter of managing professional and organizational contingencies and passing on responsibility.