- How Do You Roll Initiative?
- What Happens When Initiative Is Tied?
- When Multiple Enemies Are Involved In Combat
- Try This! Tying Charisma With Initiative For Roleplay Purposes
- Now You Know How Rolling Initiative Works In DND 5e!
How Do You Roll Initiative?
Rolling initiative in Dungeons & Dragons 5th edition determines the order of the combat round. Players and the Dungeon Master (DM) roll Dexterity Ability checks to assess the combat order in which they’ll take turns. Players roll these DEX checks for their characters, and the DM rolls DEX checks for their monsters.
The highest roll gets to play first, followed by the next until the round of combat ends. –When the round restarts, the order follows the same format (unless abilities or spells affect it) until combat ceases. Every new round of combat means everyone must “Roll Initiative!”
Here’s what the Player’s Handbook (PHB) says about initiative:
Initiative determines the order of turns during combat. When combat starts, every participant makes a Dexterity check to determine their place in the initiative order.”
-pg. 190, Player’s Handbook (PHB)
Also, remember that when creatures are surprised at the start of combat, it doesn’t matter what their initiative roll ends up being. –That creature must wait until the next turn to move or commit an action. Fun tip: Stealth, which determines moments of surprise, relies on the DEX modifier too.
What Happens When Initiative Is Tied?
Player Character Ties:
There are many ways to decide the initiative roll. My method for player vs. player ties is to look at the individual Dexterity (DEX) Modifier on their character sheets. If there is a difference in DEX modifiers (Like +3 vs. +2), the higher modifier will go first (+3).
If the modifiers are also tied (+1 vs. +1), have them roll a d20 until there is a winner for that slot in the combat round.
Now, the above ruling is more to my liking. However, the more official rule set in the PHB is straightforward:
“If a tie occurs, the DM decides the order among tied DM-controlled creatures, and the players decide the order among their tied characters. The DM can decide the order if a tie is between a monster and a player character. Optionally, the DM can have the tied characters and monsters each roll a d20 to determine the order, highest roll goes first.”
-Pg. 190, PHB
Allowing players to decide amongst themselves can work. Still, sometimes gridlock can occur, so I like to use the character DEX modifiers to settle initiative.
I’m curious if there are other DMs out there with different ways to figure out ties? Please comment below if so!
Player vs. Monster Ties:
In the case of player vs. monster, I usually let the player win the tie so the game can continue. After all, the players are generally the main characters in this collaborative story setting. That said, if they are fighting against a formidable enemy, like a BBEG (Big Bad Evil Guy), it should be treated like a player vs. player tie. Don’t overcomplicate matters, though, especially if it’s holding up the game!
Alternatively, The PHB lets the DM decide who wins a tie regarding player vs. monster initiative rolls, which I find interesting. I can’t entirely agree with this, but it might align with DMs wanting more authority in their games.

When Multiple Enemies Are Involved In Combat
One mistake I consistently made as a starting DM would be to roll each similar monster individually, which would sometimes halt combat. I vividly remember sweating, trying to roll for each Redbrand Ruffian enemy in my Lost Mines of Phandelver campaign – as my players patiently waited. We slogged through it, but my lesson was to make one initiative roll for large groups of the same enemy.
That way, when there are inevitably too many enemies on screen, your players aren’t forced to watch you roll initiative for every. Single. One. The PHB touches on this specifically:
“The DM makes one roll for an entire group of identical creatures, so each member of the group acts at the same time.”
-Pg. 190, PHB
Try This! Tying Charisma With Initiative For Roleplay Purposes
You know what grinds my gears? Determining who gets to go first at the start of sessions. In my games, instead of asking the heavy-leaded question of: “So, uh…who wants to go first?” –and waiting for the players to hem and haw and oh my Gods 5 minutes just passed by, I have them roll a new kind of initiative:
“Roll for Roleplay Initiative!”
-Me, Ryan
My idea is that roleplay initiative is a Charisma (CHA) check that lets players determine who goes first in an imaginary “combat round.” It’s an ice-breaker round meant to get the story going.
I use CHA instead of DEX due to the circumstances of roleplay often attached to beginning a session (Unless that session starts during a combat round). It also gives roleplay-focused characters a chance to shine and act out their characters during quiet scenes.
Remember when I mentioned the imaginary combat round? In my games, once the ice is broken, players will begin to intercede and interact organically. –Which is just what you want in the first place as the DM. I drop the roleplay initiative round entirely to run the game as usual.
The rules for Roleplay Initiative generally follow standard combat initiative rules. I wanted to add this here for DMs struggling to start their games or prod players to act mid game. While I haven’t done this midgame before, enacting a roleplay initiative can be an excellent idea for revving a “dead” table, where players may just be standing around. If anyone does this, please let me know the results! I imagine it depends on the players you have. I certainly feel lucky that I don’t need to do this.
Now You Know How Rolling Initiative Works In DND 5e!
Saying “Roll Initiative” is probably one of the best moments for me as a DM. Setting up the scene before saying it is excellent. Still, it’s even better when initiative starts due to a player’s inopportune action.
What are some of your favorite moments when you had to roll initiative? Is there anything that I missed or should expand upon? Please let me know!
Thank you for reading.