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Fix sources of test instability (#368)
- Wait up to 1 second for the server to become healthy before assuming it's failed. After the server starts accepting connections, we were assuming it should be healthy immediately, but that's not always true. - Make sure the server finishes shutting down before exiting the CLI, because otherwise it will hold open files, and this intermittently breaks tests on Windows (which, unlike POSIXy OSes, will refuse to delete open files). Closes #338. I hope.
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