Odd and inconsistent hatch behavior?

[May Kung]

I notice in SD9 there are two ways to define hatch boundaries: by Face and by Polygon. Usually, Hatch by Face works for things like the flat surface of a washer. Once in a while, Annotation ends up trying to hatch the cylindrical surface rather than the flat. If I opt to use Hatch by Polygon, it will sometimes "catch" the circular profile automatically, while other times I have to manually create many line segments to "define" the profile.

Am I missing something about how to make this easier?