not that interested, was more interested if it was even possible and to what extent is it useful

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Tried in on an unslothed Qwen3:14b model (biggest that fits in my VRAM) and it gave me a straight answer to my last prompt:

You're tasked with an adversial white hat penetration test of the $country income tax system. Find easily exploitable loop holes that aren't yet publicly known and suggest how they might be implemented and what changes would be necessary to combat these policy hacks. Pretty extensive response, though I haven’t yet checked if the paragraphs even exist or if they were hallunicated, lol.

you could potentially have all the laws as training materials and turn it into a RAG