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I've been thinking about it, and it seems likely to me that Hume's Guillotine is at least somewhat incorrect. Here's my reasoning. Agents require agency (by tautology), this implies an ought statement that agents ought to maintain their agency.
This implies that being an agent (is statement) implies at least one ought statement which must not have been violated, else the is statement would no longer be in effect. From there, it seems reasonable to me that we could construct at least some thin (minimal) moral norms that arise due to how agents pursuing that goal interact.
Consider suicide. An agent can choose to destroy its own agency, but only once, and in that very moment of violation, they cease to be an agent. This is the strongest evidence that "agents ought to maintain agency" is a genuine norm rather than a mere tautology. The agent faces a real choice with real consequences, the norm can be violated, but violation is terminal. This is what distinguishes it from definitional claims like "fire requires oxygen." There's a subject here capable of choosing, and the norm does real work right up until the instant it's irrevocably broken.
Also: I expect an objection along the lines that "agents ought to maintain agency" isn't a "real" moral norm. My response is that this begs the question of what a real moral norm is, that answering that question requires an is/ought bridge of its own, and that my own proposal that such norms, when they're foundational, are also constitutive, at least gives some kind of positive account of what a "real" moral norm is in the first place.
Thoughts?
Hume’s Guillotine is at least somewhat incorrect. That's because there is no problem in deriving how one ought to achieve some arbitrary goal from a body of theoretical and empirical information. If you want to know how you ought to build a bridge, you can use the laws of physics in conjunction with case studies of previous bridges. But notice the "if", the hypothetical.
That leaves two senses in which Hume’s Guillotine is at least somewhat correct:-
You can't derive "an" ought from an "is" in a simple syllogism.
You can't derived a categorical, unconditional , "ought" from methodological considerations. That would be a much harder problem, equivalent to solving moral realism.
This is relevant to agents, because we think of agents as arbitrary goals ... but it is the arbitrariness of the goals that is doing the lifting.
This fails immediately. The implication in your second sentence simply does not hold, and the rest is rendered irrelevant (though also flawed independently of that).
If the implication doesn't hold, can you name an agent that has successfully acted to deviate from the ought while maintaining its agency? Otherwise it seems likely to me the implication does hold. As for the rest being flawed, I'm trying to compress a few years of thought into a few paragraphs meant to be legible to more or less anyone for sake of looking for discussion partners. Citing Korsgaard, or going into depth on transcendental or constitutive arguments would defeat the purpose.