The thing I had to wrap my head around is: For a "classic" classifier, the classes are fixed and the data distribution is p(x,y). The calibration is checked over this single distribution. Jev makes the tasks part of the input, so the data distribution is p(task,x,y) and calibration is averaged over that joint distribution. What follows is that while for classic classifiers, calibration brakes down if your x was out-of-distribution, it can now also break if your task is out of distribution. The big question now is: Can subtle differences in phrasing your task already lead to this? And the only way to verify calibration is having ground truth data to validate on. Also: Calibration over p(task, x, y) means calibrated on average across tasks. Even an in-distribution task can be over- or underconfident while the average looks fine.