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To run guicorn from the CLI in the manner you’re describing, you may need to define a --keyfile and --certfile in order for it.
Because you referenced your Nginx setup (which had these values commented out for the self-signed cert), it looks like there may be something getting mixed up in how to connect the two; I recommend looking at this sample setup for running gunicorn with Nginx:
http://docs.gunicorn.org/en/stable/deploy.html?highlight=ssl
It contains a sample configuration for a known-working configuration, which should be able to get you started.
Best,
Joseph D. Marhee Customer Success Engineer https://digitalocean.com