Get runner tests working on Windows

Summary

Runner tests on Windows are not reliable/do not complete. This prevents us from being able to confidently release a Windows container executor.

Steps to reproduce

Run the tests

Actual behavior

First execution runs incompletely; second execution hangs indefinitely

Expected behavior

Tests should successfully complete

Relevant logs and/or screenshots

Paste any relevant logs - please use code blocks (```) to format console output, logs, and code as it's very hard to read otherwise. Please paste both build log and Runner's log.