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The last option is absolutely not unreasonable to expect people to do by hand, as the article states it’s simply a problem of tooling. JJ makes this extremely easy to do, but some of us have been doing just the same in git for a long time and it is extremely achievable once you know your way around a rebase.
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Maybe it just shows my lack of tolerance for process/overhead.

As a fellow rebase enjoyer, I will do it occasionally for smaller PRs but to me, it becomes unwieldy for large ones.

Do you have any tips or aliases that makes it more workable?

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Yep, ensuring RERERE and autostash are enabled eliminate 80% of the tedium for me, but honestly just try jj; it seriously is a gamechanger and (so far, in ~6mth of use) it has had literally zero drawbacks in comparison to git, because it is still git and if I don’t know how to do something with jj, I can use the git commands I do know and it Just Works™
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It's like switching to jujutsu gives people some kind of mental permission to do this - jujutsu justifies its existence just by that alone, really.
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I have had good success lately with asking Claude to do your last option. jj also works fantastically for this, because you can easily jj new up a bunch of empty changes with the descriptions you want to have, and then jj restore the state from your original stack into them. If the process goes poorly for any reason, you still have your original stack around.

You don’t have to do it this way, you could use the oplog to undo it all if it’s not to your satisfaction, but it’s much simpler than trying to edit the commits into the right shape directly.

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