We study an infinite-horizon optimal stopping problem for a normally reflected two-dimensional diffusion in the positive quadrant with nonsmooth max-type reward . The paper develops a conditional measure-theoretic framework for the associated reflected obstacle problem. The main innovation is to show that the stopping gain is a signed measure, not a function: the kink of generates an explicit negative surface measure on . We then prove that the correct potential representation uses the resolvent of the reflected diffusion killed on first entry into the stopping set, rather than the unrestricted reflected resolvent. Under explicit monotonicity, regularity, and measure-superharmonicity assumptions, we derive an epigraph representation, a continuation-side boundary-trace condition, and a candidate verification theorem. The framework clarifies hidden regularity and uniqueness assumptions in multidimensional nonsmooth optimal stopping.

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