In the left pick I’ve grabbed a ring and want to extrude. I’ve set my transform orientation to ‘normal’ at the bottom of the 3d view window, and the 3d cursor is showing me the desired direction. As soon as I actually press ‘E’ to extrude, the normal changes to what is shown in the right hand image.
scaling the vertices up or down even slightly and then it knows to align to the average of those normals. Might be worth reporting this on the tracker and see what they think of it, there certainly has been similar issues before https://developer.blender.org/T38592 but didn’t find a matching report.