[dustfinger]

That has been my concern as well. The script I wrote tries to bucket entries into categories, including "Backward Incompatible Change" so those are easier to spot. Since it is automated I am trading some accuracy for time saved, which seemed like the only practical choice for me, since I had to backfill a lot of history, but it’s been surprisingly decent so far.

I am also planning to add some PR templates so contributors include the context up front, which should make any release note generation more accurate.

Are you using any tooling to help with changelog curration? I know towncrier is all about fragments, so contributors must had write a brief summary of their contribution, which would be more in-line with your preference.