Abstract: Recent work quantified the notion of quantum counterfactual gain for an extended Elitzur-Vaidman bomb test style scenario, through a connection to the negativity of the Kirkwood-Dirac quasiprobability distribution. We here extend this work to identifying quantum advantage in a new scenario, which we term the ``Quantum Plumber's Problem''. In this scenario, we imagine a ``quantum plumber'', who knows that one path of an interferometer is blocked, and wants to find the optimal strategy for identifying with certainty which path this is. We discuss various strategies for a generalised path-encoded interferometer, as well as for the specific case of Hofmann's three-path interferometer, introduced in a recent analysis of the relationship between states in five measurement contexts of a three level system. We support our arguments on the relative merit of competing strategies with data collected over many simulated attempts at locating blockages. We also present results for a variant of the game in which the blockage is replaced by a non-demolition detector.