To summarize - I have a part with Z anchor set to bottom, and an outline operation with “clear top” checked. However, if anything other than “outside only” is checked, the paths for clearing the top start at the part top and go upwards to the stock top.
I tested this in multiple versions and it seems like the bug was re-introduced in 3.8 - the “clear top” function works as expected in 3.7.
Thanks for the workspace. I’m looking at it and the first cut plane is at the step down depth below the stock surface. I get the same top Z depth regardless of what which options I check.