I have mentioned before how the Ring Orientation for the exterior ring of a Polygon is significant when instantiating a SqlGeography object. In this case, a Counter-Clockwise orientation is required so that as an observer walks along the path, the interior of the Polygon is always to their left.
But, what I have never really seen documented (or paid attention to, at least) is the fact that the interior rings, or holes, of a Polygon also have specific Ring Orientation requirements.
In keeping with the "Left-handed" rule, interior rings must be defined in a Clockwise manner - the opposite orientation of the shape's exterior ring. This is because holes within a Polygon are considered to be part of the exterior of the shape, so the observer walking in a Clockwise direction is still keeping the Polygon's interior to their left.
(I should note here that the Ring Orientation for SqlGeography is the exact opposite of ESRI's ShapeFile format, which is why Ring Orientation has been on my mind for the past few days).