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So I've noticed that each time one of my messages is hit by the filter there's a webrequest to a separate page from the normal conversation. I'm playing with rerouting that request to a page that doesn't exist to force errors, and what I realized is that whenever the AI wants to write something lewd, it gets to about 80% - and then the message is replaced by something that has nothing to do with the action being performed.
I.E., I convinced Anon's Irys bot up there to breastfeed me, and multiple times now messages that were related to how she felt about her nipples or her milk were halfway replaced by something else. Need to continue playing with this.