To my knowledge, covenants would enable confirmed transactions to include “can’t spend” conditions on outputs (such as block height), but thats not quite what I’m after.

I want to sign a transaction sends to regular addresses, but includes a stipulation that the whole TX is only valid if included before some height.

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I don't think this exists. The issue I am thinking is that even if you send a transaction today, it might get confirmed next week... Heck it might get confirmed in a couple of months.

I've not thought too hard about this, but that might be the reason why it isn't possible.

Agreed that the time-to-confirm is unbounded. Nevertheless, I believe it’s within the realm of possibility for there to be such a feature. I’m fairly certain such a feature does not yet exist (and I’m aware of no proposals).