Barbed bisimilarity is a widely-used behavioural equivalence for interactive systems: given a set of predicates (denoted "barbs", and representing basic observations on states) and a set of contexts (representing the possible execution environments), two systems are deemed to be equivalent if they verify the same barbs whenever inserted inside any of the chosen contexts. Despite its flexibility, this definition of equivalence is unsatisfactory, since often the quantification is over an infinite set of contexts, thus making barbed bisimilarity very hard to be verified. Should a labelled operational semantics be available for our system, more efficient observational equivalences might be adopted. To this end, a series of techniques have been proposed to derive labelled transition systems (LTSs) from unlabelled ones, the main example being Leifer and Milner's reactive systems. The underlying intuition is that labels are the "minimal" contexts that allow for a reduction to be performed. We introduce a framework that characterizes (weak) barbed bisimilarity via transition systems whose labels are (possibly minimal) contexts. Differently from other proposals, our theory is not dependent on the way LTSs are built, and it relies on a simple set-theoretical presentation. To provide a test-bed for our formalism, we instantiate it by addressing the semantics of mobile ambients and HoCore, recasting the (weak) barbed bisimilarities of these calculi via label-based behavioural equivalences.