snap perpendicular not working

The Entity Snap "perpendicular" is not working accurately.  Try stretching an object or group of objects and snap to line perpendicular.  I wait for the tool tip, telling me the snap is engaged I release the mouse button and it lets the objects go but none on the line I was trying to align with.  If I 'shift+right-click' and select snap perpendicular it works however.

Any solutions?

Mac version 2015

Lion 10.7.5