Abstract: We derive information theoretic generalization bounds for supervised learning algorithms based on a new measure of leave-one-out conditional mutual information (loo-CMI). In contrast to other CMI bounds, which may be hard to evaluate in practice, our loo-CMI bounds are easier to compute and can be interpreted in connection to other notions such as classical leave-one-out cross-validation, stability of the optimization algorithm, and the geometry of the loss-landscape. It applies both to the output of training algorithms as well as their predictions. We empirically validate the quality of the bound by evaluating its predicted generalization gap in scenarios for deep learning. In particular, our bounds are non-vacuous on image-classification tasks.