Your Complete Guide on When to Roll in Dungeons & Dragons 5e

Dungeons & Dragons is famous for its dice. The iconic twenty-sided die is almost synonymous with the game. These dice determine what your players can do and how well they can do it, but how do you know when and what they should be rolling? I have put together an exhaustive, easy to navigate list that will ensure you are rolling at the right times.

When should you roll the dice in Dungeons and Dragons 5e? During combat, you will roll a d20 to determine initiative, for attacks, saving throws, and checks, as well as several of the smaller dice for dealing damage. Outside of combat, you will roll the d20 to determine success or failure in a number of different skills that rely on abilities, such as strength, dexterity, or wisdom.

There are a lot of opportunities to roll the dice in Dungeons & Dragons. Nearly every action will be determined by a roll of the dice, but, most often, players aren’t making straight rolls. These rolls will have a modifier added to them for proficiency in the skill set, and not all skill sets are equal.

Because of this, it can be confusing to know when an action calls for a strength check vs. a dexterity check, or an intelligence vs. wisdom check. But, depending on the skill being used, one skill could help a player while the other could hurt them, thus having a huge impact on the outcome of the roll.

The same is true for Initiative and even when not to roll and just let the player automatically succeed. All of these can change the course of the game.

When to Roll Initiative

Initiative is the order in which players and monsters attack in a single round of combat. To determine initiative order, all players and monsters should roll a D20 and add their Dexterity modifier. All combatants then take turns in combat going from highest to lowest. 

For more guidance on running combat, check out my article on New DM’s Guide to Running Combat

When the Party can No Longer Avoid Combat

You should tell your player to roll initiative only when there is no other option except for combat. If the players are trying to sneak around a creature, or are actively avoiding combat, do not roll initiative. Just because the players can see a monster, doesn’t mean they are in combat yet. However, when the monster see them, or a player makes an attack, that is a good time to roll initiative.

No Such Thing as a Surprise Round

In past additions of Dungeon & Dragons, if the party managed to get the drop on a creature, they were allowed one “Surprise Round” before rolling imitative. This is not the case with Dungeons & Dragons 5e. There is no such thing as a surprise round in 5e.

They have been replaced with the Surprised Condition determined by stealth checks and passive perception. Read more about it here!

We DMs and players alike have been reluctant to give up surprise rounds, but, technically, they are not a part of this edition’s mechanics. 

When to Roll Checks

When your players ask to perform an action, inside or outside of combat, most often you will want them to roll an ability check. The kind of check they should roll will depend on the kind of action they want to perform. To do this,

You need to ask yourself, what ability does this action rely on most heavily? Strength, Dexterity, Constitution, Intelligence, Wisdom, or Charisma? Then you will need to pick a specific skill within that category.

Choose any of the categories below to see when you should use it and view the skills within that category!

Strength Check

If players are preforming an action that relies on physical force, then they should roll a strength check. Some examples include:

  • Breaking down a door
  • Using a crowbar to pull open a chest or grate
  • Moving a heavy object
  • Holding a door shut

All of these rely on the character’s physical strength.

Skills: The only skill check that uses Strength is Athletics. If you are trying to decide if your player should roll Athletics or Acrobatics, ask yourself, “Does this action require more strength or more agility?”

Dexterity Check

Use Dexterity checks when the action being performed relies on agility, reflexes and/or balance. Some examples of actions requiring a dexterity check are:

  • Walking along a wall or ledge
  • squeezing through a small space.
  • Jumping out of a moving cart
  • Pick-pocketing, stealing or sneaking


  • Acrobatics– The ability to move with agility. Players should roll acrobatics when they want to perform an action that requires quick, graceful movements, such as jumping off a monster’s back, vaulting a wall, or sliding under a closing gate.
  • Sleight of Hand– The ability to deceptively and secretly move objects or hide actions. Players should roll sleight of hand when they attempt to pick-pocket, hide the somatic movements of a spell they are casting, or steal an object in the view of others.
  • Stealth– The ability to move in silence. Players should roll this skill when they are attempting to move quietly and unnoticed.

Acrobatics Vs. Athletics: Often times, an action can be preformed either by using sheer strength, or by using agility, such as climbing up a ledge. If this is the case, give the players the option to use either one. However, if the action clearly falls into a feat of strength or a feat of agility, do not give them an option. These two skills are not interchangeable.

Consitution Check

If the action requires a hearty physical nature or health, then players should roll a constitution check. Some examples might be:

  • Participating in a drinking contest
  • Resisting the urge to vomit
  • Eating particularly disguising food
  • Running a marathon
  • Grabbing something hot without flinching

Skills: There are no skills that rely on constitution. If you ask your player to roll a constitution check, simply have them add their Constitution modifier.

Intelligence Check

Intelligence is all about memory, reason, and logic. If players are trying recall, or figure out the significance of something, it is likely they need to roll an intelligence check. Some examples include:

  • Recalling information about creatures, history, religion or cities.
  • Making connections between events or clues
  • Decoding an encrypted message
  • Recognizing signs in nature or identifying flora or fauna
  • Recognizing signs of magic or how to break spells
  • Searching rooms for objects, hidden passages or traps


  • Arcana- Knowledge of magic and how it interacts with the world
  • History- Major events of the past. If the player is trying to recall anything about a very local, specific event, it should require at high roll.
  • Investigation- The ability to search rooms, bodies, and areas for items of importance or to uncover hidden rooms, passages, safes or traps
  • Nature- Knowledge of plants, animals, seasons, and weather. Note, this does not translate into the ability to tame or grow things, it is simply the ability to identify them.
  • Religion– Knowledge of the histories of the gods, which are benevolent and which should be avoided. Again, this does not translate to favor with the gods or their servants, only the knowledge of them.

Wisdom Check

Wisdom checks are for those actions that rely on willpower and perceptiveness. While a character with intelligence may be able to identify a black bear as it attacks the party, wise characters can spot one far enough away to avoid conflict with it altogether. Some examples of when to use Wisdom Checks are if characters try to:

  • Spot a hidden creature
  • Sense that someone is lying
  • Calm a startled horse
  • Know where to find water or food in the wild
  • Use an medicine kit to treat wounds


  • Animal Handing– Taming, calming or befriending animals
  • Insight– The ability to read the subtle cues in people to determine if they are truthful, sincere, and honest
  • Medicine– The ability to check someone’s health to know if they are stable or dying. This skill also includes and understanding of basic anatomy, healing, and stabilizing.
  • Perception– The ability to see the world around them clearly. This includes noticing things others do not, like uncharacteristic actions, changes in the environment, and spotting hidden creatures.
  • Survival– An in-depth understanding of how to live off the land. Knowledge of where to find water, certain plants and animals. The ability to notice dangerous areas and terrain.

Investigation Vs Perception: It is important to note that these two are not the same. Like with Athletics vs. Acrobatics, they can be interchangeable in certain circumstances, but they are not always. Investigation requires time. To investigate a room, the player must take time to look around it, move things aside and look closely. This is far different from perception.

Perception is about noticing things while on the move. Glancing into a room would be perception, looking through the desk of the room is investigation. If a player wanted to try and spot danger as they are walking down a path, this requires perception, as they are not taking time to investigate. If, however, they want to stop and look at a statue on that path, it would become investigation.

Charisma Check

Charisma checks are all about social interactions and confidence. When players try to persuade, intimidate, or put on a show, they need to roll a charisma check. Some examples could be:

  • Playing an instrument at a bar
  • Persuading a guard to look the other way
  • Intimidating an enemy into talking
  • Lie convincingly
  • Pretending they belong somewhere they don’t (trying to fit in)


  • Deception– Lying, pretending to be someone else, or hiding true motivations. If your player is being less than honest, they should roll a deception check.
  • Intimidation– The ability to instill fear in others. Any threats or threatening actions should roll for intimidation.
  • Performance– How well the player can entertain a crowd or perform a skill. This includes anything from storytelling, playing the lute or telling jokes to using a disguise kit drawing or painting. If it requires some kind of artistic or crowd pleasing skill, its a performance check.
  • Persuasion– The ability to win people over. If players are trying to get their way without using threats or force, then they need to roll persuasion. Note: players can gain advantage when rolling persuasion in a variety of ways, such as performing a task for the person, bribing them, or simply getting on their good side.

When to Roll Saving Throws

A saving throw is an instant response to a harmful effect. These are hardly ever done by the player’s choice. If a player is trying to avoid the harmful effects of anything, be it monster, spell, trap, or force of nature, they need to make a Saving Throw.

Sometimes spells or monster abilities will directly call for a saving throw, in this case, they will tell you which ability players should use. In other situations, as with checks, the type of saving throw they make will depend on what they are trying to avoid.

Strength Saving Throw

Resisting a physical force by strength alone.

To avoid being moved by a rush or water or air, or not be bound, players should make a strength saving throw.


  • Holding onto a tree to avoid being blow away by the wind from a dragon’s wings
  • Keeping a snake from constricting
  • Avoiding being grappled by an enemy.

Because each of these examples requires physical strength to overcome, these are all examples of strength saving throws.

Dexterity Saving Throw

Dodging out of the way of harm.

If the party trips a trap, you will want to have them make a dexterity saving throw to see who gets hit and who dodges. This is the most common of the saving throws and you will likely use it often. Here are some examples:

  • Springing a dart trap
  • Avoiding falling debris
  • Dodging area of effect spell damage
  • Staying standing during an earthquake
  • Stepping on slippery ground

All of these require quick reflexes and balance, which means they fall clearly in the dexterity category.

Consitiution Saving Throw

To avoid a hazard that will drain vitality or life, players must make constitution saving throws. Some examples are:

  • Withstanding the effects of poison
  • Enduring a disease
  • Avoiding damage from venom
  • Accidentally ingesting or breathing poisonous mold or fungi

All of these rely on the hearty health of the character to avoid the harmful effects.

Intelligence Saving Throw

If players are trying to resist effects that dull their minds to make them believe something illogical, then they need to make an intelligence saving throw. Though this is more uncommon, some examples are:

  • Disbelieving in certain illusions or spells
  • Resisting mind control or mental attacks that can be refuted with logic
  • Resisting a spell that makes the player forget

Remember, intelligence has only to do with memory and logic. If it takes willpower to avoid the effect, then they will need to make a Wisdom saving throw.

Wisdom Saving Throw

The ability to resist harmful effects using sheer willpower.

If a spell or monster is attempting to charm, frighten or otherwise effect a player’s willpower, then they need to make a wisdom saving throw. For spell effects, this is the most common saving throw. Here are some examples:

  • Abilities/Spells that attempt to charm, like Charm Person, Friend and Suggestion
  • Abilities/Spells that attempt to frighten

Most often, spells or abilities that effect the mind will say players need to make a wisdom saving throw or be subjected to the effects of the spell.

Charisma Saving Throw

A charisma save is made against anything that you resist by sheer will of personality rather than simply being aware of its unreality.

Spells that Require Charisma Saves:

  • Banishment
  • Calm Emotions
  • Dispel Evil and Good
  • Divine Word
  • escaping from a Forcecage
  • penetrating a Magic Circle
  • choosing not to be affected by a Seeming spell
  • Planar Binding
  • an involuntary Plane Shift
  • the hopelessness effect of a Symbol spell
  • Zone of Truth

Monster Abilities that require Charisma Saves include:

  • Ghost’s Possession
  • Umber Hulk’s Confusing Gaze

Determining Difficulty for Checks and Saves

Both Skill Checks and Saving Throws are rolled against a DC, or Difficulty Class. The difficulty of the task being performed determines the DC. An easy task will have a low DC, hard tasks will be higher. If the player meets or exceeds the DC, they succeed. If they roll lower than the DC, they fail. Use this chart to quickly determine the DC of a task or save:

Task Difficulty DC
Very Easy 5
Easy 10
Moderate 15
Hard 20
Very Hard 25
Nearly Impossible 30

When to Roll Percentile Dice

The two D10 dice together make something called a D100. This “percentile dice” is used to determine the percentage of likelihood that something might happen, or to choose a random effect or item. You roll percentile dice for the following reasons:

  • To choose a random effect from the “Madness Chart” found on page 259-260 of the Dungeon Master’s Guide
  • To determine the random effect of “Wild Magic” for a Sorcerer, found on page 104 of the Players Handbook
  • Optional Role Play- If you aren’t sure if an NPC character would agree to a request or do something outside their nature, you can roll a d100. Pick a range, much like a DC, and if the roll is between that range, then the character would. If it isn’t, they would refuse.
  • Critical Failure Charts- Also optional, you can roll a d100 whenever you or your players rolls a Critical Failure (discussed in more detail below). You can find these charts online or make one of your own!

When to Roll with Advantage

To roll with advantage means to roll two dice and take the higher number of the two. There are several ways players can gain advantage on a roll, such as:

  • Flanking– If two players are “flanking” a creature (one character on each side) then the attack roll has advantage against that creature. This is an optional rule found in the Dungeon Master’s Guide on pg. 251.  
  • Prone– If a creature falls prone, all melee attacks have advantage against it. NOTE: All ranged weapons attack has disadvantage on prone creatures (more on this below)
  • Spell effects– Some spell effects give advantage on attacks rolls, such as Guiding Bolt
  • Help- If one player chooses to take the”Help” action and targets a second player within 5 ft. who is performing an ability check or attack roll, the second player can roll their first check or attack with advantage.  
  • Bribery/NPC Favor– If players are favored by an NPC, or have bribed them, they could potentially have advantage on persuasion checks against that NPC
  • Inspiration- If you give a player a point of inspiration, they can then use that inspiration to gain advantage on a roll of their choice. If you want to learn more about the Inspiration system, check out my post on “When and How to Give Inspiration”
  • Taking Extra Time- If players stop and take their time with an action, such as searching a room, I always give them advantage
  • DM discretion (The Rule of Cool)- If you think what the players want to do is really cool and you are hoping it succeeds, then you can give advantage. Know why? Cause you’re the DM! You can do what you want!

When to Roll with Disadvantage

To roll with Disadvantage is the exact opposite of rolling with advantage. Players roll two dice and take the lowest of the two numbers. Like with advantage, there are many ways players can find themselves at a disadvantage in rolling.

  • Conditions– There are several conditions that can be placed on characters using magic, or simply from area conditions, which cause players to have disadvantage. Blinded, Obscured and Low Lit areas, Exhaustion, and Poisoned all force players to roll with disadvantage.
  • Working Quickly- If players are trying to hurry or move quickly, I always give them disadvantage on stealth and perception checks.
  • Acting Out of Character- If a player tries to do something out of character (mostly because they are meta-gaming) I give them disadvantage for being a jerk.
  • NPC Feelings- Just like some NPCs love you party, others probably hate them, or certain members anyway. Players should be disadvantage when persuading NPCs who don’t like them.
  • DM Discretion- If you think that player would reasonably have disadvantage to perform a task, then feel free to give it to them. Just make sure you have a good reason because you will be questioned. Every. Time.

What to Do When You Roll a Critical

Congratulations! You rolled a critical! Now what? Always make sure to have lots of fun with critical! Try to make them as memorable as possible.

Critical Success

A critical success is when the d20 lands on “20” This means the player has made a one in a million shot or hit the nail the sweet spot in an interrogation. Also called “Natural 20s” these critical successes give the players added benefits in combat.

When you or a player rolls a critical hit in combat, all the damage dice are doubled. You can do this by either rolling the normal amount of dice and doubling the damage, or by doubling the amount of dice you roll. Do not double modifiers! You only double the dice.

Outside of combat, critical success can simply become, well, successes. But players should reap some kind of added benefit for rolling a natural 20. Where it is added gold or reward when negotiating, or access to a secret item list when persuading a shop keeper for a discount, critical successes should add something.

Critical Failure

A critical failure occurs when a player (or you) roll a 1 on the d20. This means things have gone as bad as they possibly can. An attack has not only missed, but has caused the weapons to become lodged in a tree trunk, or your attempt at persuasion cause the shop keeper to call the guards. Whatever it is, it is BAD.

In combat, if a player rolls a critical failure, you can either choose to simply have them miss their target (what’s the fun in that?) or have a special consequence, such as breaking their weapon on a stone, snapping a bowstring, or hitting an ally by mistake. The choice is up to you and the consequence depends on what makes sense for what is going on at the time of the failure.

Have some fun with critical failures, they can be the most hilarious part of the game! Like the time my Storm Cleric built an altar to Kord and prayed to get back her holy symbol (which was at the bottom of a lake in a wrecked ship). I rolled a critical failure and Kord ended up reaching down from the sky, pulling the ship from the lake and throwing it at me…then taking away my powers. It was great!

When to Use Passive Perception

Passive Perception is the player’s ability to naturally notice what is going on around them. Unlike the skill “perception” which requires players to say they would like to look around, passive perception happens without the players specifically saying so.

If the players are talking, walking through a city, or any other activity, they can notice people and events happening around them with their passive perception.

As a general rule, if I know there is shady business happening in a city, or a monster lurking nearby, a set DC for different areas if a player’s Passive Perception meets or exceeds that DC, I tell them what they notice. No roll required. This is great for throwing out leads for side quests, plot development, or important NPCs.

When to Just Roll with It

How much you decide to roll is really up to you. Aside from combat and certain spells and abilities, you can have the players roll as little or as much as you want. If my players want to do something that I think would be easy for them to do, I just let them. No rolling needed. If they want to do something that is absolutely impossible and ridiculous, I simply don’t let them. No rolling required.

I have had some of the best moments come out of just sitting back and letting the players do what they want, without touching the dice once. And I have had some of the funniest moments come from critical failures and success. In the end, do what is best for your campaign and your group. Let the dice junkies roll, let the role players talk, and about all, just roll with it.

Until next time,

May your game have advantage, my friends.

-Halfling Hannah

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