Assigning advantage and disadvantage is the purview of the DM. Page 239 of the DMG reads, in part:

you [the DM] decide whether a circumstance influences a roll in one direction or another, and you grant advantage or impose disadvantage as a result

Does this mean the DM should (or must) choose either one or the other for a given circumstance, or can the DM choose to have one circumstance simultaneously apply advantage to one party and disadvantage to the other?

The books make clear that one circumstance can apply a (dis)advantage. It's also explicit that multiple circumstances can apply to a contested roll, resulting in possibly multiple parties receiving an advantage and/or disadvantage. I'm interested in whether or not a single circumstance can simultaneously impose advantage on one party and disadvantage on the opposition on the same check.

The example situation in the book on the following page gives multiple examples of (dis)advantage in a wizard-vs-ogres situation. However, all of these examples are one party vs. the environment or some other context, not compared to the other party.

Here's one situation where a contested roll might have ambiguity on which party should get the (dis)advantage [which leaves open the option that they both get it simultaneously from one circumstance]. A and D are wrestling. A is much larger than D. Does A get advantage, D disadvantage, or both?

  • \$\begingroup\$ Could you provide another example? As far as I know, "advantage" and "disadvantage" modifiers are applied due to environment circumstances. For circumstances like "the opponent is larger" or "the opponent is stronger" we have respective stats ("size" and "strength" in this case), and aren't suppose to use advantage-disadvantage mechanics. \$\endgroup\$
    – enkryptor
    Oct 1, 2016 at 12:27
  • \$\begingroup\$ @enkryptor I chose that example specifically because that's how it came up in the answer linked under "both" (the last word in my question). I think it's a good enough example to illustrate intent. Even if it runs afoul of the grappling rules, it's still a DM call on who gets advantage when. If you have a better example, I encourage you to edit it in. \$\endgroup\$ Oct 5, 2016 at 3:37

5 Answers 5


Yes, A DM could impose disadvantage and grant advantage on the same contest.

There is precedent for it. The Cloak of Elvenkind grants both advantage and disadvantage to a Wisdom (Perception) vs Dexterity (Stealth) contest. From the SRD:

While you wear this cloak with its hood up, Wisdom (Perception) checks made to see you have disadvantage, and you have advantage on Dexterity (Stealth) checks made to hide, as the cloak's color shifts to camouflage you. Pulling the hood up or down requires an action.

It is therefore possible to imagine other situations in which a Dungeonmaster could grant similar concurrent bonuses/penalties. Note that items which do this are very few. A ruling such as this based on a current situation should be just as rare. Advantage vs Disadvantage contests are pretty much a foregone conclusion, and almost beg the question "why bother to roll?"


Your example is a poor choice because wrestling is covered by the grappling rules and if A is more than 2 size categories larger than B then B can't grapple A at all, if not there is no effect due to size.

Notwithstanding, an effect can only push one way on a given roll and it's a DM judgement call on which way that works. Sticking with grappling, imagine B is covered in butter and therefore slippery as an eel.

If A initiates a grapple on B, I would rule that this gives A disadvantage on he check as the butter causes their grip to slip; B is unaffected. If B tries to grapple A then B gets the disadvantage as B's hands are slippery.

If B is grappled and trying to escape its more of a close call: is A disadvantaged in holding on or is B advantaged in slipping away? If B is trying to escape using Strength (Athletics) then maybe the butter has no effect as all: this is a brute force contest in which slipperiness plays no part. If using Dexterity (Agility) the butter would come into play. There is no objectively right answer here so use your own judgement and then be consistent.

Be aware that there is a mechanical impact to this if there are additional sources of advantage/disadvantage. For example, if our buttered up hero is exhausted, they already have disadvantage on ability checks; giving them another has no effect but giving their opponent advantage has a huge affect.

In general, think about if the circumstance applies to one character more than the other: if so apply the advantage/disadvantage to them.

  • \$\begingroup\$ I agree the example isn't great, but I took it explicitly from the now-linked q&a. In fact, my comments on that answer show I don't think the example works at all, which might be why I had trouble coming up with another one. \$\endgroup\$ Sep 30, 2016 at 22:35
  • \$\begingroup\$ I've updated my question to clarify that I'm looking for one circumstance conferring multiple (dis)advantages in one contest. However, your line "an effect can only push one way on a given roll" seems like it answers that question. \$\endgroup\$ Oct 1, 2016 at 2:33

You could, but it would be largely pointless.

There could certainly be a situation where you could, technically, apply advantage to one side and disadvantage to the other side in an opposed check. For example, if two people were competing in a simple footrace: one person might have special knowledge of the course, and get advantage, while the other is winded after running all day, and has disadvantage.

However, if you have a situation like that, the chance of the disadvantaged character succeeding is very slight. The rule of thumb when applying advantage or disadvantage is to add or subtract 5 to the normal modifier to get a ballpark estimate of where the (dis)advantaged roll will lie. In the case where one side has advantage and the other has disadvantage, it's statistically similar to adding +10 to the advantaged roll. In a case like that, it's very unlikely for the disadvantaged character to win.

If you're doing a contest between characters with vastly disparate skill levels, then giving advantage to the lower-skill character and disadvantage to the higher-skill character could be a way to even the odds, and make the roll interesting. If both characters have similar skill levels, there isn't much point in rolling for the check. If you want to roll it anyway, that's your prerogative, but I'd rather just declare "there's no way Mr. Disadvantage is winning this one" and move on rather than spend time on a check like that.

  • \$\begingroup\$ I've updated my question to clarify that I'm looking for one circumstance conferring multiple (dis)advantages in one contest. It does get a bit more interesting again when advantages and disadvantages cancel. \$\endgroup\$ Oct 1, 2016 at 2:30
  • \$\begingroup\$ It's not that unlikely. Using pure d20s with no modifiers, a disadvantaged character will still defeat an advantaged character about 15% of the time (with another 3% or more being ties); that's just the same as needing an 18+ on a pure d20—not fantastic odds, but quite possible. \$\endgroup\$
    – user31662
    Oct 1, 2016 at 7:43

I'm not going to use the Grapple as an example to answer this question. I will however say that Yes, there are situations where one event can confer advantage for one party and disadvantage for another.

The example I will use is that of a Warlock with Devil's Sight and a Darkness spell. A Devil's Sight Warlock can see through magical darkness. When both the Warlock and an opponent are within magical darkness and the opponent has no means of seeing / sensing through it, then the Warlock has advantage on attack rolls since his opponent is in effect Blinded. The opponent however has disadvantage on attack rolls for the same reason.

from the Player's Handbook, pg 290:


Any attack rolls against the creature have advantage, and the creature's attack rolls have disadvantage

The same effect would hold true even if the opponent was outside the magical darkness and the Warlock was within - at least in a contest between the two of them - since the Warlock can still see the opponent, but the opponent cannot see the Warlock. In this instance, I would say the Warlock is Invisible to the opponent.

From page 291 of the PHB:


Attack rolls against the creature have disadvantage, and the creature's attacks have advantage.

Another situation that can confer advantage to one party and disadvantage to another would be if one party were in some fashion (and there are multiple ways for this to happen) Restrained.

From Page 292 of the PHB:


Attack rolls against the creature have advantage, and the creature's attack rolls have disadvantage

I would say that each of these situations can arise in a variety of ways, and there could be a number of other situations that might cause the advantage/disadvantage event.


Typically any situation which favors one and disfavors another is already covered by rules in the PHB or flat out ruled impossible.

For instance the case of size you listed above is already factored into grapple checks: PHB 195

The target of your grapple must be no more than one size larger than you, and must be within your reach.

In the context of the grapple, size is already considered as trying to grapple something that is more than one size larger is flat out deemed impossible. While you are always allowed to try to escape from the grapple at no penalty.

However, assuming that context was not there, the game rules imply that the advantage or disadvantage only happen once for a specific favorable condition - at the discretion of the DM of course. So if you were going to impose adv or disadv based on size, you should not apply advantage to the check made by the grappler and also impose disadvantage to the person trying to avoid it without having a different reason while the person avoiding it should receive disadvantage. (For instance, the grappler is larger than the grappled target and the grapple target just happens to be blinded by a spell).

PHB 173 If multiple situations affect a roll and each one grants advantage or imposes disadvantage on it, you don't roll more than one additional d20. If two favorable siutations grant advantage, for example you still only roll one additional d20.

These rules don't explicitly prevent the DM from doing what your suggesting, but consider the conflicts you can create if you assign advantage and disadvantage this way. Use the following example to see the potential problems:

I could pose advantage on the grappler initater's contest check because he's large. The opposed check for the contest is either Strength (Athletics) or Dexterity(Acrobatics). Thus I could rule that because of your size difference your Strength isn't likely to help you so your Strength(Athletics) roll if used suffers disadvantage as well but your Dexterity isn't directly affected by my opponents size so I may rule my Dexterity(Athletics) is unaffected. Lets say you do cover yourself in something slippery, you could receive Disadvantage to your Strength(Athletics) if used to defend against the grapple but receive Advantage to your Dexterity(Acrobatics) used to prevent a grapple.

As you can see this does serve inhibit the defending player's ability to use Strength while still making the grappler have a strong roll regardless of which roll the contested opponent uses.

However, you will notice the contradiction in rationalization that I just made in the roleplay. I just tried to impose both advantage to the attacker and disadvantage to the defender -okay good so far. However, as the defender, I ended up using my dexterity which I ruled wasn't affected by size, but then I gave advantage to the grapple iniater's check because of size. So I essentially imposed a penalty to the grappled persons role by ruling the grappler gets advantage, and my reason for imposing the penalty is no longer valid and rational.

This is why the notion of advantage and disadvantage is typically unidirectional. In the example it would have been more appropriate to leave the grapple initiater's check alone but impose disadvantage on Strength check of the grapplee. It is not pointless to do this at it inhibits the defending character's ability to use Strength to counter the grapple, and capture's your point that size is a problem. In this context however, the attempt to avoid the grapple is not "impossible" if I attempt to use my Dexterity.


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