Bad Idea. It is very dangerous becuse the feet of the ladder sitting on a pitched roof can easily kick out. When they do, the lack of bearing is multiplied greatly causing you to fall. This will more likely happen when coming off the higher roof. If you do decide to use this technique, make sure your in the middle field of the first roof to set the ladder, then secure the top of the rails to the gutter, make sure not to have too much extension so to properly be able to round the ladder on your desent. Too short of an extension is bad too. Aproximatly 2' is good. Your first step when desending is most important. Adjust the ladder so the first run is about 10" from roof line for good footing. Always have your cell phone with you when on a roof and secured well to your body. Best if you use two ladders so that a helper can hold the ladder for you if situation is available. Avoid this situation with one ladder if possible.[:-thumbd