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I am looking to run a web app on PythonAnywhere that receives requests from webhooks, and a Discord bot as an always-on task that sends messages based on the payload received (and in this case, by the web app). The question here is whether the communication between a web app and an always-on task is possible, and if yes, how could I go about doing it?

Thanks.

Have a look at this help page (there's a blog linked with an example as well). Basically the communication through web app and the Always-on task would be via a database.