We present experimental results on the extraction of oil trapped in the confined region of a wedge. Upon addition of a more wetting liquid, we observe that oil fingers develop into this extracting liquid. The fingers eventually pinch off and form droplets that are driven away from the apex of the wedge by surface tension along the gradient of confinement. During an experiment, we observe that the size of the expelled oil droplets decreases as the unstable front recedes towards the wedge. We show how this size can be predicted from a linear stability analysis reminiscent of the classical Saffman–Taylor instability. However, the standard balance of capillary and bulk viscous dissipation does not account for the dynamics found in our experiments, leaving as an open question the detailed theoretical description of the instability.