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Particularly the hard scenarios, with a squash-based GH repo, and maybe a small actual merge conflict. How well does GitButler support such real life scenarios?

GitButler supports first class conflicts similar to JJ letting you perform a rebase and resolve conflicts as needed. Detecting integrated squash commits is a difficult problem. We do try to detect them, but sometimes they slip through. We are are actively trying to improve this system.

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Ooh, you even attempt to detect squash commits? That's cool. I'd love to see more about this Tricky problem to solve 100% in general of course, as the client is not in control of squashing and other commits could have landed onto a PR concurrently.