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We extend the data-driven approach to inferring preconditions for code from a set of test executions. Prior work requires a fixed set of features, atomic predicates that define the search space of possible preconditions, to be specified in advance. In contrast, we introduce a technique for on-demand feature learning, which automatically expands the search space of candidate preconditions in a targeted manner as necessary. We have instantiated our approach in a tool called PIE. In addition to making precondition inference more expressive, we show how to apply our feature-learning technique to the setting of data-driven loop invariant inference. We evaluate our approach by using PIE to infer rich preconditions for black-box OCaml library functions and using our loop-invariant inference algorithm as part of an automatic program verifier for C++ programs.