tl;dr don't turn on all the checks for a subset of files, check as many files as possible and add checks on a module-by-module basis This post is a bit of a response to some online complaining by Armin Ronacher about mypy. While I agree in the abstract that mypy-s payoff feels less nice than Typescript's, I spent 30 minutes or so looking at Sentry's codebase and felt that Armin's problems are not "just" mypy problems, but problems compounded by how Sentry is choosing to adopt mypy. Adding typ...