it seems like a bug,
it can’t handle bridge between loops that on the same surface angle.
If you rotate slightly cube edge loop it bridge as expected.
I think it some sort of limitation for bridge tool, but would be nice if it could work like your first examples.
Experimented with angles when bridge start to work as expected and found angle in 6.36 degree, below this angle - not working.
or in blender - help - report a bug
if you report a bug, pls, put a link here, I want to subscribe
Don’t bother reporting, there’s one in from over 2 years ago. Might be worth adding that the report was resubmitted because the guy reporting it couldn’t find his several years old report from the last time he put it in.
Please report this as a new bug. While T54996 is a complex case which fails, this has a more obvious solution as this is not “multiple rows of faces facing each other”.
cant even understand how it chooses normals.
I think best solution in this case will be add option to Reverse direction or even Reverse Direction for both selection individually: “Reverse first Direction” and “Reverse last Direction”
P.S. can’t upload blend file…