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I am new to D&D 5th ed. I have purchased the books but not played in a group. One of the first big things I see is that advantage (or disadvantage) replace most of the die roll modifiers.

Is there EVER a case where more than 2 dice are rolled? (either adv. or disadv.)

I have seen the probability charts that display exactly what the 2nd d20 does on advantage or disadvantage, to your probability of rolling a certain number or higher. Is there ever a case, in the DMG, etc., where a DM might choose, or would be recommended to, ask player(s) to roll a 3rd die? (I.e., that those graphs should be a bit more sloped.)

Example: What if a rogue has a modifier that gives advantage to climb a wall. (feat, special gloves, etc.) If it is also raining, the wall is covered in algae, and he has a wounded thumb, do the + and - really just cancel out, so he has a straight chance? Or would these hypothetical disadvantages just add to the DC?

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Advantage/Disadvantage NEVER uses more than 2 dice

With one weird exception: The Lucky feat allows you roll 1 extra dice (after rolling the first 2) and pick 1 of the dice you rolled. This can turn advantage or disadvantage into a kind of super advantage especially since you can see the first 2 dice before spending a luck point. Obviously, lucky people can be more lucky when they are really pushing their luck.

There are other features (e.g. halfling luck) that may cause one of these to be rerolled but that is not an extra dice - it is one of the originals. The difference is only semantic pedantry but I like semantic pedantry.

You only roll when there is a chance of success or failure

If the advantage/disadvantage is so overwhelming that the creature CAN'T fail/succeed then don't roll dice - they just do/don't do it.

You set the DC and you decide what constitutes advantage/disadvantage - they are independent mechanics

In theory, the DC represents the inherent difficulty and advantage/disadvantage represents situational effects. Where you draw the line between them is your ruling and as DM, you can't be wrong about it.

However, there is guidance:

  1. If a rule says it affects DC, or adds a modifier (they do still exist), or gives advantage/disadvantage - do that.
  2. If it is a permanent feature of the challenge - lean towards the DC.
  3. If it is a temporary or intermittent effect or something that affects only some creatures - lean towards advantage/disadvantage.

For your example:

  • "feat, special gloves, etc." - the rule says advantage so advantage it is.
  • "raining" - could go either way - if its always raining like in a rainforest then change the DC, if the PCs can wait for the rain to stop then make it disadvantage.
  • "algae" - sounds permanent to me - DC. If the PCs remove the algae somehow then change the DC.
  • "wounded thumb" - not really a thing that D&D contemplated but OK. Its temporary - disadvantage.

So the algae makes the Easy (DC10) climb Medium (DC15). 1 advantage and 2 disadvantage means neither. Roll 1 dice against DC15.

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    \$\begingroup\$ @LinoFrankCiaralli Yep - fixed that \$\endgroup\$ – Dale M Jan 16 '18 at 0:05
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    \$\begingroup\$ The Elven Accuracy feat allows you to reroll 1 of the 2 d20s when you make an attack with advantage. \$\endgroup\$ – AprilRyanLavellan Jan 16 '18 at 11:00
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    \$\begingroup\$ @jasonfm Lucky is a weird outlier, and stands on its own as a curious example of this edition's quirks. It doesn't work for every roll, but when it works it works ... luck > skill. \$\endgroup\$ – KorvinStarmast Jan 16 '18 at 16:56
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    \$\begingroup\$ Weird as it is, lucky can easily turn a terrible situation into an amazing one. 2d20l1 becomes 3d20h1 (rolz.org syntax). Lucky overrides the Disadvantage mechanic (specific beats general) unless fixed in future errata. \$\endgroup\$ – Nick Brown Jan 16 '18 at 18:23
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    \$\begingroup\$ They talked about Lucky extensively in the Sage Advice bit in the DragonTalk podcast for 12/1/2016. He said that in the Sage Advice article, he gave a RAW ruling that Lucky on a Disadvantaged roll let you pick any of the three dice; but the 'as intended' version (and what he uses in his game) is that you roll your 2d20 and take the lowest; that's the initial result of your roll, then roll the Lucky die and pick either that die or the initial result die. (i.e., the 'high die' from the initial 2d20 roll is gone by the time you decide to use Lucky) \$\endgroup\$ – Darth Pseudonym Jan 16 '18 at 20:00
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The Lucky Feat

PHB pg. 167, pertinent text cited:

You have 3 luck points. Whenever you make an attack roll, an ability check, or a saving throw, you can spend one luck point to roll an additional d20.

The only current case where you can get "greater advantage" is with the use of the Lucky Feat. If you choose to utilize one of your Luck Points, you may roll an additional die during a time when you have advantage or disadvantage, and then pick any of the three die to use.

Other than this, there isn't a mechanism for greater advantage/disadvantage.

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  • \$\begingroup\$ OP's question: Is there EVER a case where more than 2 dice are rolled? (either adv. or disadv.) Also, that's not what lucky says. It says you can use any of the dice, unless this was errata'd somewhere I can't find. \$\endgroup\$ – Lino Frank Ciaralli Jan 15 '18 at 23:42
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    \$\begingroup\$ mobile.twitter.com/JeremyECrawford/status/600731432437174272 \$\endgroup\$ – NautArch Jan 16 '18 at 0:02
  • \$\begingroup\$ It seems, from the twitter comment by JECrawford, that (with the Lucky feat) that you get a reroll, on one die of the 2 rolled, in an advantage or disadvantage roll. That means, you sort of (semantics) get the best d20 out of 3 d20s, on advantage. But, I do not see how that prevents you from having to pick the worst die for disadvantage. Best case, you get to reroll the lowest, and so you could effectively chose the 2nd lowest out of the 3. \$\endgroup\$ – jasonfm Jan 16 '18 at 2:00
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    \$\begingroup\$ The feat literally says: You choose which of the d20s is used for the attack roll, ability check, or saving throw. RAW, and you may refer to the tweet above for confirmation (even though he admits to wanting it redesigned in the future), lucky+disadvantage = roll 3 and pick any of them. \$\endgroup\$ – Nick Brown Jan 16 '18 at 18:21
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    \$\begingroup\$ @jasonfm In the DragonTalk podcast for 12/1/2016, Sage Advice section was all devoted to Lucky. According to Jeremy, the intent is that advantage/disadvantage applies first, before you 'use' Lucky. If you have disadvantage and use Lucky, you roll your 2d20 (say, 18 and 4) and pick the lowest (the 4) -- that resolves the disadvantage. Then roll an additional d20 (say, a 12), and pick whichever of those two (4 and 12) you like best. (That isn't precisely what the text says, but as he says many times in the episode, that's what they meant to happen and how he runs it at his table.) \$\endgroup\$ – Darth Pseudonym Jan 16 '18 at 21:22
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Elven Accuracy

No, but... with Xanathar's Guide to Everything, the Racial Feat Elven Accuracy allows you to reroll one die in some situations. From XGtE, p74:

Whenever you have advantage on an attack roll using Dexterity, Intelligence, Wisdom, or Charisma, you can reroll one of the dice once.

This effectively gives a third die.

Anydice: http://anydice.com/program/1e0a

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