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IANAL but isn’t it illegal to execute something in the event of a document not being signed?

I expect not... provided it's a thing you could do anyway (and it isn't extortion or something).

You could claim you gave someone a contract and they didn’t sign it, so now they owe u a million bucks

I think you missed my proviso.

If you can do X in the first place, I don't think there's any general rule that you can't condition X on someone not signing a contract.