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spelling words wrong and using figurative or garbled speech trips them up, and another way to test if someone is a bot is to ask them to draw a simple picture in mspaint (e.g. "a house with a red '4' to the left of it") and then reciprocate, so you know you're having a convo with an actual human and vice versa
unfortunately, the majority of 4chan pass users are bots, so don't expect jannies/mods/admins to ever give a shit