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I am running a production app on PythonAnywhere. I know its a little crazy but its easy for me.

Anyway, myself and some of my users have had intermittent issues logging into the website, instead being booted to the 502-backend error page instead of properly logging in. I have experienced the issue only once myself and could only fix it by clearing the cache on my browser.

Is there anything I can do to prevent this issue from reoccurring or is it an inherent problem with SQLite/Flask/PythonAnywhere?

P.S. A minor tangent but is there a way for me to customize the 502-backend error page? It would be very useful

There are many things that can cause a 502 error, so we have a help page to help you to debug it: https://help.pythonanywhere.com/pages/502BadGateway/

You cannot customise the 502 page.