I would use standoffs and put on the shingles there, I myself don’t lay ladders on gutters.
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Yeah, the ladder isn’t sitting properly but I need that angle for the roof hook on the end of my ladder to hook the railing. The roof line under the railing keeps the ladder from reaching the railing and I need to be able to grab the railing before I get off the ladder.
Those railings aren’t always secured the best, if the ladder touches the gutter as you are climbing, it can fulcrum. Put a bullhorn on it and rest it on the shingles. Be safe. I know you probably are, I worry about safety more as I get older.
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