[HayZee518]

I don't think there's a proper way of placing a ladder against a gutter so as not to smash or dent the gutter. My thinking is that the ladder's upper rails should be on either side of the nail and sleeve that holds the gutter to the fascia board. If the gutter is pvc, then I would opt spending a few bucks and get a ladder stand off that clamps to the upper part of the ladder. This would distribute weight over a longer distance and be away from the house surface. It's just a "U" shaped aluminum piece of square tubing with rubber crutch tips on the ends. Keeps the ladder about a foot off the surface.