The theoretical framework of the paper combines the notions of school disengagement and educational trajectories. Our current research has demonstrated that several trajectories of school disengagement can be distinguished: "unanticipated crisis, parabola, downward spiral, boomerang, resilient route, shading out." The text focuses on two trajectory types -- the parabola, when youngsters facing increasing school disengagement are provided with substantial support and their trajectory changes its direction, and the downward spiral, which despite the support leads to further school disengagement and school leaving. Analysing the educational biographies of students from secondary schools in Warsaw, we focus on their perceptions of the support provided by different formal and informal sources. Investigating the protective factors and successful interventions might thus be useful in fostering the educational success of youth at risk. An analysis of the trajectories might be treated as guidance as to how to offset the negative impact of social and educational inequalities and hence to reverse the negative direction in one's educational trajectory. The text is based on qualitative analysis of data obtained within an international research project: individual semi-structured interviews with Polish students at risk of early school leaving and youngsters who left school early.