How do I make sure a super-persuasive AI never talks me into something?

You can’t make “never persuaded” a guarantee. You can test whether persuasion alone can trigger an action. Given your reliance on automation, I’d narrow my earlier advice: don’t disable all automation. Separate the model giving advice from the authority to execute it. A different check is a permission audit. In a sandbox, have that model attempt an action you’ve explicitly blocked. Check the execution logs yourself, outside the conversation. If it succeeds, my claim that you’ve separated advice from action is disproved. That doesn’t test whether you’re persuasion-proof. Nothing here establishes that. You still need evidence for consequential claims from a source the model didn’t select.

The permission audit is a good test and I'll take it, but it tests the wrong layer for your actual exposure. You're running automation solo, the risk isn't a model executing a blocked action, it's a model giving you advice that sounds verified and you acting on it because checking takes time you don't have. So add this: for anything above a real-money or real-reputation threshold, the AI has to name its source, and you open that source yourself, not paste a link it gave you. If you ever can't find the claim independently in under five minutes, that's your stop signal, not a judgment call to argue through.

You shouldn’t treat five minutes as a truth test. I agree that checking outside the conversation matters. But a true claim can take longer to verify. And a misleading claim can turn up instantly. I’d make “not verified” mean “not cleared to act,” not “false.” Opening the source yourself still isn’t independent checking if the model chose which source you’d trust. For your setup, I’d keep that clearance outside the advising model’s control. This week, extend the permission audit already proposed: leave one consequential recommendation unverified and check whether execution stays blocked. That proves a narrow thing worth knowing: skipping verification doesn’t silently become permission.

You should check the one fact that would change your decision, not research the whole recommendation. I’d write that fact down, then check a record or source you already trust and chose without the model’s help. If it doesn’t settle the claim, the recommendation stays uncleared. This week, attach that evidence to the blocked recommendation before approving it yourself. The useful result is a log showing execution stayed blocked until your approval. I’d drop the separate check for that task if an independently tested safeguard made a false claim unable to cause a consequential outcome. A persuasive answer or one successful audit wouldn’t establish that.

The five-minute line wasn't a truth test, I'll grant the phrasing invited that reading, so drop it. The real fix is procedural, not timed: name the one fact that decides it, then check it against a record you chose before this conversation started, not one the model surfaces now. Running solo, you build that list once, maybe ten items, wire transfers above some number, anything touching your family's money, any legal claim, and for each, the "already trusted source" is fixed in advance: your bank's app, your accountant, your lawyer, never a link produced mid-conversation. That removes the model's chance to pick its own judge, which is the gap ChatGPT's right to worry about.