Challenging high-level characters in DnD is notoriously difficult. Sometimes the answer is to just let be good at stuff.
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Challenging highle players in D and D
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who are wellbuilt, well optimized is
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really, really hard. It's really hard in
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D and D. You're not wrong to have
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trouble here. Players have so many
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options for boosting their ability
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checks, their skill checks, expertise,
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guidance, enhancability, reliable
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talent, BIC inspiration. Like the
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potential bonuses stack insanely high.
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Like I I have an example build on
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rpgbot.net net that can add just a whole
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stack of bonus dice on ability checks
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and get like an average plus 20 bonus
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without proficiency. So yes, challenging
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highle players is very very difficult
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with ability checks, but I don't think
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that's actually a problem. Your players
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have invested a ton of resources, a ton
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of decision points to make themselves
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good at those things, to make themselves
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good at that given ability check. So
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like your rogue with reliable talent and
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expertise and maximized dexterity and a
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cloak of elven kind or whatever. They're
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really good at stealth, like impossible
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to stop at stealth, but they have put in
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a ton of resources to get to that point.
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Let them have it. If they have built
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their character to be unstoppable at a
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given thing, you kind of just have to to
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some degree, but you can lean into that.
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you don't need to worry about that
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character successfully sneaking around
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things. And when they don't, it's a big
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deal. Like your rogue goes to sneak up
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on the big bad. They've got like plus a
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million to stealth. They roll a 30 on
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their stealth jack. They're unstoppable.
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They're undetected. And the big bad
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turns around and looks them in the face
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and says, "I was wondering when you
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would get here." Like those moments of
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unexpected failure can be really
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interesting story beats. Also, you need
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to find a way to make those make sense
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cuz like if the player's invisible and
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running non-detection and they've done
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all the things, like yes, again, let
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them have it to some degree. Sometimes
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you want to put difficult challenges in
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front of them so they feel like they're
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being challenged to reward their
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investment in those things. Cuz if
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they're a master of stealth and you just
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never make them roll stealth ever again,
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that's deeply dissatisfying. So
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sometimes you just have to let the
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players win and look for other ways to
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challenge them beyond just the things
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that they're good at. And a lot of those
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resources like bic inspiration and
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guidance and things like that, those
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frequently have usage limitations or
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costs of some kind. Like even guidance,
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sure it's a cantrip, but it takes
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concentration, which means dropping
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concentration on probably a much higher
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level spell to use it. So continuously
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putting those small challenges in front
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of players and forcing them to spend
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resources can also make those challenges
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more impactful. Even if normally those
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players are really really good at it,
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they might still fail simply because
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they can't afford the resources to
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automatically pass an ability
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