Building natural language inference (NLI) benchmarks that are both challenging for modern techniques, and free from shortcut biases is difficult. Chief among these biases is single sentence label leakage, where annotatorintroduced spurious correlations yield datasets where the logical relation between (premise, hypothesis) pairs can be accurately predicted from only a single sentence, something that should in principle be impossible. We demonstrate that despite efforts to reduce this leakage, it persists in modern datasets that have been introduced since its 2018 discovery. To enable future amelioration efforts, introduce a novel model-driven technique, the progressive evaluation of cluster outliers (PECO) which enables both the objective measurement of leakage, and the automated detection of subpopulations in the data which maximally exhibit it.