In an example method, a system obtains, during a first subterranean drilling operation, first data indicating one or more characteristics of a drill bit of a drilling system, second data including sensor measurements regarding the drilling system, and third data indicating historical information regarding one or more additional subterranean drilling operations. The system determines a first metric based on the first data, a second metric based on the second data, and a third metric based on the third data. Further, the system determines a fourth metric based on the first metric, the second metric, and the third metric, where the fourth metric is indicative of a risk of a stuck pipe in the drilling system during the first subterranean drilling operation. The system generates a graphical user interface for presentation to a user, including an indication of the fourth metric.