There is an issue when applying a thread to a hole with a chamfer. The modeled threads do not extend past the chamfer. There is a workaround where you can suppress the chamfer, add threads and then unsuppress. Not ideal in my opinion.
The countersink in the hole command does the same thing when selecting a tapped hole. Can this issue be fixed please?
The first issue applies to threads on a cylinder with a chamfer also i believe?
This should also work with a fillet as well though probably not as common.