I'm using discord webhook so that everything said in-game is outputted into a discord channel. I have it working, however, when there are too many people talking in-game, it times out.
I checked the wiki and it says there's a max of 500 requests per minute - but, how much is that? What is it counting? There aren't 500 messages being sent per minute.

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How do I know when I've sent too many requests though? I could try making a queue but I'd like to know how much to output a minute.
Well, as you said, requests are capped at 500 per minute. I never have reached that much. The best way to know how many requests you're sending a minute is by in each script that either GetAsync or SetAsync, have it add +1 to a global variable. Check it
Are you constantly reading from the Discord chat?