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Message: <blockquote data-quote="Quickleaf" data-source="post: 8190850" data-attributes="member: 20323">That's key information. There was no time pressure. And, as I'm reading "no immediate guards", there was no threat of being discovered while breaking in.So I think the question to ask is: What was at risk? What was at stake? What was unknown?From your description of the "old, crumbling 80-foot tower wall with loose bricks and few handholds", my impression is that what you wanted to have at risk was the actual physical climbing ability of the person doing the unassisted solo free climb and potential for falling as a consequence. If they succeed, they attach the anchor, and everyone else can climb up without needing a check.The DC is going to be somewhere >15 (free hanging rope with no handholds/footholds) but <20 (vertical freeclimb of natural rock with few handholds, climbing a rockfall with a rope in terrible weather or under fire). DC 17 or 18 feels about right.Then, I'd look for ways to add more nuance to a failed check. So fail by 5+ would be outright falling somewhere mid-climb (20 feet + 1d4x 10 feet worth of fall damage). But a fail by 1-4 would indicate an interrupted climb with some kind of complication. For example, falling to a lower balcony for 1d6 or 2d6 damage and smashing through a window as they roll. Or someone opening up a window and emptying a night soil bucket. Or falling bricks creating a hazard for allies below, and making the climb for allies harder. Basically, failing by 1-4 is any sort of complication short of "you fall and fail." But failing by 5+ is the "big fall."EDIT: Oh! If they went the "I want to throw the grappling hook up 80 feet" (and assuming they had long enough rope), I'd consider using either an improvised ranged attack roll (AC 9), a Sleight of Hand check, or a Strength (climber's/mountaineer's tools) check... with disadvantage for long range. A failed check by 1-4 would mean the grapple gets hooked on the wrong thing, and now they have to figure out how to extricate it, while a failed check by 5+ might indicate the rope gets cut on some architectural protrusion and they lose the grappling hook on a balcony or neighboring rooftop.</blockquote>

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