When to use Advantage/Disadvantage
Essentially, an advantage allows you to roll 2d20, taking the higher roll result, whilst a disadvantage requires you to roll 2d20, taking the lower result. You never roll more than two dice because multiple advantage/disadvantage conditions don’t stack. If you have conditions that give you both advantage and disadvantage, they cancel each other out and you get neither.
It is up to the DM do decide if you get advantage or disadvantage on a roll. When trying to determine if a situation warrants an advantage or disadvantage, it may be helpful to review the specific situation listed in the PHB. This list does not include special abilities or magic spells or magic items.
Advantage
- If you have inspiration, you can expend it when you make an attack roll, saving throw, or ability check. Spending your inspiration gives you advantage on that roll.
- Using a crowbar grants advantage to Strength checks where the crow bar’s leverage can be applied.
- A magnifying glass grants advantage on any ability check made to appraise or inspect an item that is small or highly detailed.
- A military saddle gives you advantage on any check you make to remain mounted.
- When mounted – You have advantage on melee attack rolls against any unmounted creature that is smaller than your mount.
- Helping another with a task (where your assistance could actually be of help) adds advantage to their check.
- If you are hiding – “the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen.”
- When a creature can’t see you, you have advantage on attack rolls against it.
- Attack rolls against a blinded creature have advantage.
- Invisible creature’s attack rolls have advantage.
- Attack rolls against paralyzed and petrified creatures have advantage.
- An attack roll against a prone creature has advantage if the attacker is within 5 feet of the creature.
- Attack rolls against restrained or stunned or unconscious creatures have advantage.
Disadvantage
- If you wear armor that you lack proficiency with, you have disadvantage on any ability check, saving throw, or attack roll that involves Strength or Dexterity.
- If the Armor table shows “Disadvantage” in the Stealth column, the wearer has disadvantage on Dexterity (Stealth) checks.
- Small creatures have disadvantage on attack rolls with heavy weapons.
- In lightly obscured areas – creatures have disadvantage on Wisdom (Perception) checks that rely on sight.
- When attacking a target beyond normal range, you have disadvantage on the attack roll.
- You have disadvantage when you use a lance to attack a target within 5 feet of you.
- When you attack a target that you can’t see, you have disadvantage on the attack roll.
- You have disadvantage on a ranged attack roll if you are within 5 feet of a hostile creature that can see you and that isn’t incapacitated
- Blinded creature’s attack rolls have disadvantage.
- Attack rolls against Invisible creatures have disadvantage.
- Any level of exhaustion gives you a disadvantage on ability checks
- A poisoned creature has disadvantage on attack rolls and ability checks.
- A prone creature has disadvantage on attack rolls.
- An attack roll against a prone creature has disadvantage if the attacker is more than 5 feet from the creature.
- Restrained creatures have disadvantage on Dexterity saving throws and attack rolls.
Dungeon Master Assistance 
Great recap. I love the idea of this system and thought it was one of the finer parts of the 5E revamp. I just haven’t been able to get a group together to try it… maybe I can convince my wife and teenage kids to play…
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I am in a similar boat. Fortunately, my wife loves to play. Unfortunately, I don’t have a regular group to play with., My daughter is grown and lives 1000 miles away.
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Last night the PCs were going through a tunnel that they basically had to crawl through. I decided that any attacks they made in the tunnel would be at a disadvantage, unless they were small in size. It is an elegant mechanic, and does not require wondering / arguing about whether it is a -2 or a -4, etc. Players just accept it and go with it when you say, “You will be at a disadvantage when attacking while in that tunnel..”
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Thanks for this excellent example of how you are using this is actual game play. I completely agree that this mechanic makes this version of the game run much smoother than earlier versions.
If anyone else has an example they would like to share I am sure everyone would like to hear about it. You never know when a snippet like this is just what someone may need to help them with their game tonight.
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outside of the normal context and examples, my group found a +1 mace blessed by the Morninglord, and when you call on him it does bonus damage to undead. My cleric player wanted to take it, and so the special stipulation I put on it was that when using it normally you swing like normal. But once you call on Lathander you swing at disadvantage because he is not your deity and it upsets Ohgma that you have called on the blessing of another god
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So I am new to D&D and i’m trying to learn so I can play in my community however I am having some trouble with understanding if things cancel each others out. I have created a paladin with 16 strength, 17 dex, and proficient in stealth due to background before I even got to look at armor. Now I am looking and the chainmail I receive has a disadvantage on stealth. Can anyone explain to me how that would particularly work out because i don’t know if they would cancel each other or I would have to roll and add modifier or if I just roll and choose the lowest. I am so confused.
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Hi Clora,
Welcome to my site and to the D&D game.
You are correct that having both advantage and disadvantage will cancel each other out. But being proficient in stealth is not the same as having advantage in stealth. I simply means that whenever you make a stealth check, you roll a d20 and add your character’s proficiency bonus. When wearing Chainmail armor, a character has disadvantage on stealth so when he makes a stealth check he rolls two d20s and takes the lowest number rolled.
So, if your Paladin is wearing Chainmail armor, when you make a stealth check, you roll two d20s, take the lower of the two, then add his proficiency bonus and his ability modifier to that number.
At first level, your proficiency bonus is +2
For stealth checks the ability you use is dexterity, and with a 17 DEX the ability modifier is +3
Putting this all together it works like this:
Assuming your Paladin is first level with a dex of 17 and wearing chainmail armor (his strength has no effect on stealth checks).
Let’s say he wants to make a stealth check. First you tell your DM what you are attempting to do. You might say something like, “The thief spotted a group of Orcs standing around the other side of this wall. Sir Galahad is going to try to sneak up on them.” The DM might say, “OK they can’t see you now, so go ahead and make a stealth check.”
Then you roll two d20’s. Let’s say you roll a 10 and a 14 (you have disadvantage because your chainmail is noisy). you have to take the lowest number (10) and then you add your dexterity modifier (+3) and your proficiency bonus (+2) for a total of 15 (10+3+2=15).
In the games I run, I will tell the player to write that number down and I will use it as the DC (Difficulty Class or target number) for any creature that makes a perception check to notice you. I will have them roll another stealth check if the situation changes. Some DMs wait until a creature tries to notice you before they have you make a stealth check.
You will have to decide if wearing heavy armor is worth having disadvantage on stealth rolls. For most Paladins is probably is. They are not known as being very stealthy. They tend to prefer stepping up to their opponents and changeling them to an honorable combat.
I hope this helps and may all of your d20 rolls be natural 20s!
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Thank you for breaking that down. I just started playing with my wife and children, who are new to the game. It’s been almost 20 years since my last game, and some of these nuances in 5e are tricky to sort out. Fun tho!
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You are very welcome. I am glad to help.
Let me know if you run into anything else confusing.
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Just a tiny critique. With the elven accuracy feat, it shows a contradiction to your statement that you will never roll 3 D20s.
Also curious about your stance on using the lucky feat when you have disadvantage?
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Three comments regarding the elven accuracy feat.
1) This post, “D&D 5E – Advantage/Disadvantage” that you are responding to, was posted in 2015. The “Elven Accuracy feat first appeared in “Xanathar’s Guide to Everything” that wasn’t published until 2017.
2) I realize this is splitting hairs, but it doesn’t technically have you roll 3 d20’s. “Whenever you have advantage on an attack roll using Dexterity, Intelligence, Wisdom, or Charisma, you can reroll one of the dice once.”
3) Because it is not in the core rule books, it is not available to everyone. I don’t allow my players to use feats from “Xanathar’s Guide to Everything”.
Using the Lucky Feat when you have disadvantage is a more interesting question. I have struggled with this in the past and here is what I came up with.
I thought that the rules as written didn’t work for disadvantage. If you roll three D20s and take the highest when you have advantage works, but taking the lowest of 3 when you have disadvantage makes it less likely to succeed which is deficiently not lucky!
So I went back to the PHB. It says “if a halfling has advantage or disadvantage on an ability check and rolls a 1 and a 13, the halfling could use the Lucky trait to reroll the 1.” The Lucky Feat would work the same way.
In practice, players with the Lucky Feat will normally roll 3 d20s and take the highest when rolling with advantage. When rolling with disadvantage, they can roll 2 D20s, then reroll the lowest. Or can roll 3 D20s and discard the lowest (taking the second lowest). It all works out the same.
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