Tuning compiler optimizations for rapidly evolving hardware makes porting and extending an optimizing compiler for each new platform extremely challenging. Iterative optimization is a popular approach to adapting programs to a new architecture automatically using feedback-directed compilation. However, the large number of evaluations required for each program has prevented iterative compilation from widespread take-up in production compilers. Machine learning has been proposed to tune optimizations across programs systematically but is currently limited to a few transformations, long training phases and critically lacks publicly released, stable tools. Our approach is to develop a modular, extensible, self-tuning optimization infrastructure to automatically learn the best optimizations across multiple programs and architectures based on the correlation between program features, run-time behavior and optimizations. In this paper we describe Milepost GCC, the first publicly-available op...