We consider the structured-output prediction problem through probabilistic approaches and generalize the “perturb-and-MAP” framework to more challenging weighted Hamming losses, which are crucial in applications. While in principle our approach is a straightforward marginalization, it requires solving many related MAP inference problems. We show that for log-supermodular pairwise models these operations can be performed efficiently using the machinery of dynamic graph cuts. We also propose to use double stochastic gradient descent, both on the data and on the perturbations, for efficient learning. Our framework can naturally take weak supervision (e.g., partial labels) into account. We conduct a set of experiments on medium-scale character recognition and image segmentation, showing the benefits of our algorithms.