In this article, I discuss educational boundaries as experienced by the learner across different contexts, activities and interests. Learning is understood as a trajectory beyond situated contexts. The analytical focus is how learning trajectories are experienced as continuity or discontinuity by students across in-school and out-of-school settings. The analysis draws on findings from a longitudinal project in one multicultural community of Oslo, using mainly observational and interview methodologies. The findings show that educational boundaries are often blurred and represent different learning trajectories beyond simple dichotomies of continuation or discontinuation in learning.