Title: Quantifying Task Complexity Through Generalized Information Measures. Abstract: How can we measure the “complexity” of a learning task so that we can compare one task to another? From classical information theory, we know that entropy is a useful measure of the complexity of a random variable and provides a lower bound on the minimum expected number of bits needed for transmitting its state. In this paper, we propose to measure the complexity of a learning task by the minimum expected number of questions that need to be answered to solve the task. For example, the minimum expected number of patches that need to be observed to classify FashionMNIST images. We prove several properties of the proposed complexity measure, including connections with classical entropy and sub-additivity for multiple tasks. As the computation of the minimum expected number of questions is generally intractable, we propose a greedy procedure called “information pursuit” (IP), which selects one question at a time depending on previous questions and their answers. This requires learning a probabilistic generative model relating data and questions to the task, for which we employ variational autoencoders and normalizing flows. We illustrate the usefulness of the proposed measure on various binary image classification tasks using image patches as the query set. Our results indicate that the complexity of a classification task increases as signal-to-noise ratio decreases, and that classification of the KMNIST dataset is more complex than classification of the FashionMNIST dataset. As a byproduct of choosing patches as queries, our approach also provides a principled way of determining which pixels in an image are most informative for a task.