To Roll… or Not to Roll? 

When to Roll Dice in Dungeons and Dragons

Recently, one of our blog posts detailed the 7-polyhedral dice set you need to play Dungeons and Dragons. We explained each die and their specific purposes in the game. 

But sometimes you need something other than an exact definition! It’s good to know what each die can do, but dnd is situational, you have to know which dice is right for that situation.

A helpful, typical D&D example is needed… an entertaining and informative illustration that explains when to roll dice...

What follows is a summary of a hypothetical session of Dungeons and Dragons. This mini-adventure will be played between three friends: two players (Ranger and Bard) and the Dungeon Master (NPC’s, monsters, Wizard).

The adventure will show many of the most common elements found in an average session of Dnd, including exploration, role-playing, and combat. When a player or DM does something that requires a roll, it will be showed in (parentheses). 

NOTE: This post focuses specifically on helping players know when to roll which Dnd dice. But a majority of the time no one is making ‘straight rolls’. After most rolls you only determine the result AFTER you have added a small number based on your characters particular skills, known as an “ability modifyer”  For a simple explanation of modifiers check out this post or this video


The Heroes Arrive to Town (Role-Playing)

Our story begins as two adventurers, a Ranger and a Bard, enter a small country town. While the Bard buys food for future travels, the Ranger seeks a blacksmith to gain a new arrowhead. The Ranger, a responsible elven girl, asks the blacksmith some questions about the town and if anyone is hiring for odd jobs. The Bard feigns poverty in an attempt to get a bargain (Deception, D20). Failing, he resumes his cool human with a laid back attitude, and the general store owner for the best place to chill and get a drink. 

The general store owner and blacksmith are complex characters, but not essential to the story. So rather than spend valuable time imagining, The Dungeon Master (or “DM”) had them randomly generated by consulting the pages 89-90 of the Dungeon Master’s Guide. On those pages he found random tables and  rolled for their appearance (D20), abilities (D6), mannerisms (D20), traits (D12), and bonds (D10). 

If the Dungeon Master wanted to randomly generate the feel and details of the town, or what types of businesses the adventurers could find there, they could have used pages 112-113 in the Dungeon Master’s Guide. 

But back to the story…

The blacksmith tells the ranger of a Wizard on the far side of town who might have a job or two. Once reunited, the Ranger convinces the slothful Bard that it’s important they seize opportunities like this (Persuasion check, D20) and they agree to get some more money before resting at the tavern. 

The Bard and Ranger walk to the Wizard’s home which, being magical, looks strange and potentially threatening. The Ranger tries to see if there is some sort of trap (Investigation check, D20). Confident that it is trap-free, she knocks on the door. 

Upon realizing they were sent by the blacksmith, the dwarvish Wizard welcomes them inside a small home cluttered with books and esoteric ingredients. He explains that a carriage delivering his small chest of family trinkets went missing in the forest. He is willing to award 10 gold pieces to each person who helps secure its return. 

The job sounds simple enough, but the Bard is unsettled by the urgency of the Wizard, and senses (Perception check, D20) that the Wizard wants the package for some rare spell...

But also… money! So they head off into the woods to get the package.


Into the Woods (Exploration)


The Ranger and the Bard travel for a few hours along the south road out of town. Eventually, Ranger notices some carriage tracks that lead off the road and into the woods (Nature or Perception check, D20). This leads them deeper into the woods… and into the path of a fearsome… bunny rabbit?!

They could have run into wolves, or an ancient shrine, or bandits… but the DM rolled a D100 on his own random forest encounter table, so bunny rabbit it is! 

Instead of pulling out her bow and having a mess on her hands, the Ranger lets the bunny scamper away and instead forages for berries (Survival check, D20) before resuming tracking the carriage.

They soon stumble upon a carriage in shambles and torn to pieces, the Ranger tries to determine what ruined the cart (Investigation or Nature check, D20) while the Bard looks for the chest (Investigation check, D20). The Ranger is relieved they ran into a bunny rabbit rather than an owl bear. 

The Bard finds the chest a few yards away in the bushes, but he can’t help his curiosity… so he attempts to pick the lock (Sleight of Hand check, D20). He fails to open it, but based on the designs and artisan handiwork of the chest (Arcana check, D20), they realize something very important and magical must be in the chest 


The Heroes Return for Payment (Role-Playing) 

The Ranger and Bard return to the Wizard, chest in hand. Suspicious it is worth more than just 20 gold pieces, they attempt to barter with the  Wizard for more money (Persuasion check, D20). They roll very low, so the Wizard not only refuses but changes his tone... 

He impatiently assures them the chest contains family heirlooms worthless to strangers. He further explains that not only can he not pay them any more, but they agreed to the 10gp/person payment anyways. Seeing his temper so suddenly escalate, the Bard remains suspicious, and can tell that the Wizard is hiding something (Insight check, D20). He demands further payment or at least an explanation of what is inside. 

Panicked, the Wizard lunges to try to take the chest, but the Ranger moves the chest out of the way (Sleight of Hand check, D20). The Wizard, enraged, begins casting a spell. 


Roll initiative...


It Comes to Blows (Combat) 

First Round: 

Each person rolls a D20 to see who goes first… which ends up being 1) the Bard, 2) the Wizard, and then 3) the Ranger. 

The Bard begins by casting “Charm Person” on the Wizard to deescalate the situation, but he is already antagonistic the Wizard rolls with advantage (D20 twice, take the highest). Seeing his spell had no effect, the Bard uses his bonus action to give “Bardic Inspiration” to the Ranger, which allows her to add 1d4 to her attack roll. 

The Wizard then casts burning hands, forcing the Ranger to roll a D20 to dodge out of the way. She fails, and as the flames sear her body takes 3d6 of damage. With flames whirling around her, the Ranger knocks and looses an arrow, rolling a D20 (and rolling a 1d4 due to the Bardic Inspiration), it hits, and she rolls 1d8 to determine damage. 

That is the end of the first round, so back to the top...


Second Round: 

The Bard, lays his hand on his friend and casts “Cure Wounds”, which allows the Ranger to heal 1d8 of health back. 

The Wizard tries to cast Blindness on the Bard, but he rolls a D20 and succeeds in his Constitution save. The ranger then drops his bow and pulls out a double-bladed axe, rolls a D20 to attack and hits, doing 1d12 of damage to the Wizard. 

And back to the top, but before the third round can begin...

A double-bladed axe wound is not a pretty sight. Low on health, the Wizard throws up his hands asking for mercy, effectively ending the combat. 


Aftermath and Reward

Rather than commit murder, the Bard and Ranger say they are going to keep the chest and take  the key to open it. The leave and immediately head straight for the tavern.

With food and drink in hand, the exhausted Ranger and Bard rest at their table for a short while. During this time they both use their hit dice to heal. The Bard rolls 1d8 and the Ranger rolls 2d10, gaining a little health for the time being. 

After their meal, they could head to their rooms and gain all their health with a long rest, but first they take the key and open the chest to reveal… 

...hold on… the DM forgot to put anything in the chest! So he turns to page 134 of the Dungeon Master’s Guide to randomly generate loot, and rolls a D12, D10, and D6...

… to reveal a moonstone, a pearl, and a ruby! 

That's a total of much, MUCH more than 20 gp! Excited over their new wealth, the Ranger and Bard order another round. 


End of session 


While just about ANYTHING can happen in a session of D&D, that mini-adventure contained many of the key elements: exploration, role-playing, and combat. Overall, two things should stand out to you: 


  • You roll a D20 WAY more than the other dice

  • If, as a player, you want to do something you could potentially fail to do, your DM will ask you for a Skill check to determine whether you succeed or not. 

  • There are many instances where whether or not you roll is up to the discretion of the DM. 

    Hopefully all that helps and makes your introduction to D&D a little less disorienting! Remember: it takes a little time to get used to all the modifiers and numbers and rolling. 


    But before long, you two could write up a hypothetical mini-adventure just like this one. And just like I did, you can do it all WITHOUT EVER CONSULTING THE RULES! 


    That’s how second nature it becomes.


    (Except for the page numbers… I didn’t know that…) 

    Articles by rathDndHow to

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