Agreed; however, since this is HN, I'd like to suggest that it should be totally doable to improve on the squashing workflow using tooling. Programmatically it'

Agreed; however, since this is HN, I'd like to suggest that it should be totally doable to improve on the squashing workflow using tooling. Programmatically it's easy to verify that the signed-off commits induce the same diff as the squashed commit; they're either equal or not. Then, if the interface where signoffs are registered (e.g. github PR) enforces that all PR's are signed off while allowing a squashed, un-signed-off commit if it has the same diff as a signed-off commit, then you can squash at will. Optionally you could also require that the signers additionally sign-off the final commit, under the tool-provided guarantee that the diff is identical.