The study of loss function distributions is critical to characterize a model's behaviour on a given machine learning problem. For example, while the quality of a model is commonly determined by the average loss assessed on a testing set, this quantity does not reflect the existence of the true mean of the loss distribution. Indeed, the finiteness of the statistical moments of the loss distribution is related to the thickness of its tails, which are generally unknown. Since typical cross-validation schemes determine a family of testing loss distributions conditioned on the training samples, the total loss distribution must be recovered by marginalizing over the space of training sets. As we show in this work, the finiteness of the sampling procedure negatively affects the reliability and efficiency of classical tail estimation methods from the Extreme Value Theory, such as the Peaks-Over-Threshold approach. In this work we tackle this issue by developing a novel general theory for estimating the tails of marginal distributions, when there exists a large variability between locations of the individual conditional distributions underlying the marginal. To this end, we demonstrate that under some regularity conditions, the shape parameter of the marginal distribution is the maximum tail shape parameter of the family of conditional distributions. We term this estimation approach as cross-tail estimation (CTE). We test cross-tail estimation in a series of experiments on simulated and real data 1 , showing the improved robustness and quality of tail estimation as compared to classical approaches, and providing evidence for the relationship between model performance and loss distribution tail thickness.