I don't know if it's an issue with Webpack, or something else, but sometimes after deploying new asset changes, they don't necessarily take effect unless I clear my browser's cache.
A documented example: T207776#4892987
Webpack is giving it a new file name as it should (example). It's possible the issue is specific to the code for T207776, but I don't really understand how clearing the cache a single time would fix it.