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Prior, I had no issues reloading the webapp. However now, it's always returning the timeout error.

My error log only returns: 2020-02-12 02:34:26,478: OSError: write error

How can I troubleshoot this?

It looks like it took more than 10 seconds for web app to respond to the first request from our infrastructure after reloading. The app reloaded happily, but slowly.

You can add some logging to see how long does it take for different stages of your web app to get ready.