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Message: <blockquote data-quote="Fanaelialae" data-source="post: 7239824" data-attributes="member: 53980">Outside of combat (where a more nuanced resolution is warranted) I'd ask for a single roll. I find that asking for multiple rolls is punitive (unless it's a group check). It's a level 11 rogue with 20 Dexterity and expertise in stealth. Pretty standard actually (albeit tier 3). Reliable talent allows them to treat any roll of less than 10 as if it were a 10. Certainly an extremely skilled character, but IMO giving them right of free passage is too much in this scenario. One or two guards and/or good cover, maybe. But not in the case of a hundred guards with minimal cover. The fact that I would let it be attempted at all would speak volumes of the rogues skill, and the 95% chance of success would say volumes more. Sure, the Eagle Eye scenario is fine. That's a reasonable way to go. This Eagle Eye must be AMAZING though if he has a chance to spot what one hundred other guards couldn't. I realize that D&D is in many ways part of the superhero genre, and your suggestion works very well in that respect. However, I like it when on occasion the mooks can spot Batman. It shouldn't ALWAYS take a super villain IMO. Even superheroes should slip up on occasion. It keeps them more grounded and relatable (which is why I prefer "normal" Batman over the basically superhuman version of Batman when he's with the Justice League).The average guard is no match for the master sneak. But a hundred of them very well might be. The odds are very much against them, but there's a chance nonetheless.</blockquote>

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