My conclusion is that OpenAI will help you with cybersecurity and never really block or prevent you from doing the work, but then suddenly warn and/or ban you. Anthropic does the opposite, where they trigger safeguards all the time while working, but never really ban you.

Also, while you may have never heard of this happening I found countless threads on Reddit with frustrated people having been banned from OpenAI for using it for cybersecurity. Since all I’m using AI for is cybersecurity, it’s hard to know exactly why I was banned since they don’t say exactly why.

I tried to appeal, hoping their automated system would take pity on me but predictably it was instantly denied lol

Now granted, I was doing actual offensive cybersecurity work without being enrolled in the cyber program, and I have plenty of spare alternate accounts anyway so it wasn't that big of a deal. It actually already net me a few 0days, so their guardrails aren't very effective.