Running Boss Encounters

Running Boss Encounters in 5E D&D

The archdevil Zariel descends from the crimson sky amidst a pitched battle between demons and devils, teeth bared and weapons ready to tear the party asunder.

The Frostmaiden turns her otherworldly gaze upon the characters, her fierce, azure eyes promising a quick and cold death.

The Xanathar appears from thin air, its ten eyestalks pointing directly at the heroes, its fanged mouth open in a maniacal grin.

Boss encounters are a quintessential part of 5E Dungeons & Dragons and other tabletop roleplaying games. This encounter is usually the climax of the adventure, where the characters must face their hardest challenge yet, as they put their lives on the line to vanquish the villain in an epic showdown!

Yes, expectations are high. We expect boss encounters to be more than just another encounter – more deadly, more dynamic, and more dramatic.

But, running boss encounters is difficult. Too often, what we get fails to live up to these lofty expectations, leaving everyone at the table feeling disappointed – and none more so than the DM.

In this article, I’ll take a closer look at how to run boss encounters that live up to expectations – without getting out of hand!

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Running Boss Encounters

Let’s start by defining what a boss encounter is, so we can better understand why it’s so challenging to run. A boss encounter is typically:

  • The final encounter of the adventuring day, adventure location, and/or the whole adventure!
  • Against one or more enemies that are extra strong and/or extra important.
  • More deadly, dynamic, and dramatic than “regular” encounters.

Of course, there’s various degrees of boss encounters, ranging from the unnamed troll at the back of the Troll’s Cave to the evil dragon that the characters have been fighting against throughout the whole adventure. But, whether it’s just a session mini-boss or a campaign-finale encounter – as long as it fits mostly within the above definition, I’ll call it a boss encounter.

High Expectations

The above definition also handily tells us why it is so challenging to run a boss encounter: our expectations that it is more than a regular encounter.

Our idea of the archetypical boss encounter has been instilled in us from movies, books, and other works of fiction, where the hero(es) final confrontation with the villain is usually the most deadly, most dynamic, and most dramatic battle of the entire story.

Running and balancing any D&D-encounter can be difficult, but having high expectations such as these certainly doesn’t make it any easier.

You want your boss encounter to be difficult and deadly, so victory feels earned – but if you make it too hard, you end up killing the party.

You want to make the boss encounter exciting and dynamic – but if you overdo it, you end up with a complex and overlong encounter that exhausts and confuses not only the characters but also the players.

You want the boss encounter to be cinematic and dramatic – but what happens when your players interrupt the villain’s monologue with an ambush or decide to flee right before they would have earned glorious victory in a dramatic turn of events?

Any DM who has run a few boss encounters knows how difficult it can be to overcome these challenges. Luckily, there’s something to be done about it – and this is where we arrive at the point of this article.

Running Boss Encounters

Running Better Boss Encounters

Time to roll up our sleeves and take a look at how we can run the best boss encounters possible. The first, and probably most important, challenge we have to overcome is difficulty.

Difficulty – Balancing Boss Encounters

Both DMs and players expect the boss encounter to be the most difficult and deadly encounter they’ll face. Like in our favorite movies, we want the encounter to end up with the heroes bloodied, exhausted, and an inch away from utter defeat, but somehow still managing to just eek out a last-minute, well-deserved victory.

But while we want the boss encounter to feel almost unwinnable, we still want to make it very likely that the characters win in the end – it’s their story, after all. And, that’s a hard balance to strike.

Giving specific advice on how to balance encounters is impossible without knowing the party and the monster they’re facing, but there’s some general tips it pays to observe for any boss encounters:

  • Action Economy. If you have a singular boss, make sure the characters can’t overwhelm it with actions by either allowing it to use (or giving it) Legendary Actions or Lair Actions, or by giving it minions that can help balance out the characters’ actions and help shore up the boss’s shortcomings.
  • Quick Calculations. Take a quick look at the average hit points and expected damage outputs for both the boss monster(s) and the characters and make just a few, quick calculations. If you can see that the adult black dragon has ~200 hit points and deal ~50 damage per round, while the four 10th level characters have ~80 hit points and deal ~30 damage per round each, you don’t need to be a mathematician to see that the dragon will be hard-pressed to properly challenge the characters unless given additional actions, more hit points, or minions.

Now, these tips will help you balance the boss encounter initially, and who knows, you may get lucky and strike the exact right balance. When that’s not the case, it pays to have a more versatile tool at hand: Difficulty Dials.

Balancing Boss Encounters: Difficulty Dials

So, what do you do, when the characters prove to be much stronger than anticipated and are handily defeating your boss without ever rolling a Death Saving Throw, or two critical rolls from your boss cuts the party in half in the first round?

Well, you turn the dials, of course. The Difficulty Dials, that is – dials you’ve set up in advance, because you knew something like this was bound to happen. I’ll explain.

Have you ever run an encounter that proved too easy or too difficult, where you ended up (quite obviously) fudging saving throws, attack rolls, and/or hit points to make up for it, or committing the DM’s cardinal sin of introducing an DMPC to swoop in at the last minute and save the day? 

While doing these things may work in a pinch, they never feel good – and more often than not, the players can tell what you’re doing and that hurts their excitement. So how can you avoid having to make these impromptu readjustments at the last minute to save an encounter? 

By planning them out in advance and implementing them as soon as you see where things are heading.

When you prepare for the session, take 5-10 minutes to consider how you can rebalance the encounter, should it prove too difficult or too easy. Which monsters could show up to aid the villain if it’s going down too fast? What could happen to increase the characters’ odds of success if things are starting to look too bleak too soon?

Then, as you’re running the encounter, try to stay aware of how the fight is going. As soon as you can see where things are heading, turn the dial to make the encounter easier or harder. By reacting early, rather than at the last minute, you can avoid a situation where NPC(s) have to swoop in to save the day and finish the encounter for the characters, robbing them of most of the satisfaction. Instead, help arrives in time to bolster the characters, soak some damage, and turn the tide – but not completely take over the show!

Here’s two quick examples of how this could look:

EXAMPLE 1: The characters are facing a mighty lich, which should have been more than enough of a challenge for them! But, using clever tactics, the characters have managed to restrain the lich and it looks like it’ll go down too fast. Luckily, you were prepared for this, and the lich’s shield guardian arrives via dimension door to aid it’s master, instantly doubling the lich’s effective hit points and increasing its AC.

EXAMPLE 2: The characters got unlucky against the ancient dragon and failed horribly against its breath weapon, putting the cleric down early and decimating the rest of the party. You’ve planned for this, however – a long-forgotten moonblade calls out telepathically to the fighter from the dragon’s hoard, and when he picks it up, casts mass cure wounds and bless on the entire party, renewing their chances.

Should your first reaction end up being an overreaction, making an encounter that was too difficult suddenly too easy, you can then turn the other dial, once more recalibrating the encounter’s balance.

These dials work fine as simply “if, then” scenarios, but you can make them as advanced as you want to by setting up multiple dials or having incremental dials (I.E. two minions show up this round, then two more each round until the encounter seems better balanced, and so on.). Another benefit of planning out and using difficulty dials is also that it makes the encounter more dynamic – which is what we’ll take a look at next.

Running 5E Boss Encounters

Dynamic – Making Boss Encounters Exciting

Our second expectation for boss encounters is that they are dynamic and exciting, filled with unexpected reversals, cool effects, and difficult choices.

If the encounter was a scene in a movie, we’d want it to be directed by Michael Bay or Joss Whedon, with characters flying all over the place, explosions going off left-and-right, while the villain and the characters go back-and-forth in a desperate struggle.

However, sometimes an encounter with an epic foe – whether that’s a mighty dragon or a clever sorcerer – will look cool in theory, but end up being a slog in practice.

This is especially true for creatures that have limited action options, as they end up feeling like huge bags of hit points that can deal a lot of damage, but do little else. Thus, although difficult enough – the villain has a lot of hit points and does a lot of damage – a head-on combat encounter isn’t very dynamic or exciting.

There’s two different ways to approach this issue: altering the monster and altering the scenario.

Dynamic Monsters

Fifth edition D&D is one of the most approachable editions for a new DM to pick up, which it owes in no small part to its (comparably) simplistic monster design. Especially the classic monsters featured in the 5E Monster Manual can often be a bit one-dimensional and… yes, I’ll say it: boring. 

Take for example the titular monster of Dungeons & Dragons: the fearsome chromatic dragon. It has a mighty Breath Weapon, which is fun, but it can only be used so often, and it only deals damage – no additional effects. Its Frightful Presence offers some effect, but once it’s saved against, it’s gone. Only dragons old enough to have Legendary Actions and Lair Actions can do something other than dealing and taking damage, and even so, only sparingly. In essence, the dragon’s actions on its turn are almost always the same: attack with bite and claws or use its Breath Weapon if it’s available.

So, when preparing an encounter with the boss, make sure to consider its statistics. Does it have something exciting to do each round? Does it have reactions, bonus actions, Legendary Actions, Lair Actions? Does it have actions or spells that can alter or effect the battlefield in other ways than just dealing damage? Does it have different options available to it for different scenarios?

If not, give it these actions. Supply the dragon with some cool and powerful spells (dragons in older editions nearly always had spells) and allow it to swallow its enemies or fling them away with its tail. 

Consider this example of an adult black dragon from the Enhanced Chromatic Dragons compendium (changes and additions marked in red):

It’s not necessarily that much more powerful than a regular dragon, but it is much more dynamic and versatile, which means it will make for a much more exciting encounter. It can swallow a pesky foe, fling the paladin away with its tail, and use Withering Breath to weaken its foes, making them ripe targets for its evil spells. 

But – and this is important – it doesn’t have too much to do. It only has three spells, so you don’t have to flip through the books looking up 20 different spells each turn, and while it can do more different things in a turn, it’s not actually doing more things on its turn.

This is important to keep in mind when you’re making your villain more dynamic: don’t overdo it. You want to have dynamic options, but not to the point where you become overwhelmed and end up making the encounter boring because you can’t decide what to do.

Dynamic Scenarios

Another way to make the boss encounter more dynamic is to put some extra effort into the scenario. A head-on fight with a dynamic and dangerous foe can be exciting enough, but you can make it even more exciting by changing the circumstances and perhaps even the purpose of the encounter.

Maybe the evil warlock has opened a portal to the abyss, which is spewing forth terrible demons until the characters manage to close it. Maybe the encounter takes place in a zone of wild magic, which causes weird magic effects to happen randomly each round. Maybe the fierce battle causes the villain’s lair to collapse, and the characters must choose between killing the villain, saving the innocent captives, and getting out alive.

Adding in these extra effects and additional goals instantly makes the encounter more dynamic and challenging. Even if the characters ignore them and still treat the encounter as a head-on battle, that’s still a choice they’ve made.

The danger of making the encounter more dynamic, however, is that you risk over-complicating the encounter, making it difficult to run and confusing to the players. Try to keep this in mind and avoid coming up with effects that have you or the players making multiple rolls each turn to determine which random effect occurs and how it affects them. Stick to relatively simple but consequential effects, such as:

  • At initiative 20 each round while the portal to the Abyss is open, roll a 1d4.
    1: 3
    dretches come through; 2: a vrock comes through; 3: a barlgura comes through; 4: a chasme comes through.
  • At initiative 20 each round, each creature must succeed on a Dexterity saving throw or take 2d10 damage from stones falling from the ceiling. On a critical failure, a creature takes double damage and is restrained by stones until itself or another creature can extricate it.
  • The villain’s acolytes are scrambling to sacrifice the innocent townsfolk, and each villager they sacrifice to their evil deity gives the villain temporary hit points and advantage on attacks. Meanwhile, the villain fights to distract the characters – so do they try to take the villain down fast or go for the acolytes?

Of course, you don’t have to go all-out and create dynamic effects such as these. Sometimes, simply having a few pools of lava or acid around the chamber, placing a couple of traps in opportune places, or having plenty of objects to hide behind, jump atop of, or use in creative ways, is enough to make the encounter more dynamic. 

As long as you avoid an encounter where the characters and villain are just facing off against each other, slowly whittling down each other’s hit points round-by-round without much movement or change in tactics, you’ve succeeded in making the encounter more dynamic and exciting

Dramatic – Making Boss Encounters Cinematic

Finally, we expect our boss encounters to be dramatic. An epic monologue, a heroic last-stand, and the final, awe-inspiring attack that finally puts the boss down! This isn’t as much about game mechanics as it is about roleplaying – after all, even though we’re rolling dice, it’s not just a tactical war game we’re playing: it’s a roleplaying game.

However, creating drama is hard under the best of circumstances and even more so when you’re working within the framework of an encounter. Because as soon as initiative is rolled – or even before it – the players’ focus usually switches from roleplaying to game mechanics. 

Which means that the rogue isn’t about to give the villain an opportunity to welcome the party to its lair with a monologue, he wants to sneak attack the bastard before it knows they’re there! And, the cleric isn’t about to stop and trade insults with the villain while her bless spell is running out!

Sometimes that’s okay, but other times you want to create that additional drama. One way to do that is to let the players know that you’re entering “cinematic mode”. This is the same as when a cutscene begins before or even during a battle in a video game – the game pauses and the players have time to speak with the villain. 

When you’re in “cinematic mode”, the following rules apply:

  • Durations of spells and effects are effectively paused, so the players aren’t incentivized to interrupt the villain prematurely.
  • Both player characters and the villain can gain no tactical benefit from prematurely interrupting cinematic mode (i.e. “I attack the dragon mid-sentence to get a surprise round or advantage on the attack!”).
  • Both player characters and the villain can attempt to take advantageous actions (i.e. by casting cure wounds on themselves, standing up from prone, sneaking behind the villain, or moving to a more advantageous position), but the DM decides when and how the action resolves, as to not interrupt the cinematic sequence.

Here’s an example of how that could look:

DM: The mighty dragon Klauth shrugs off the fighter’s heavy blows and draws its head back, looking more than a little wounded and with a new-found respect for your powers. Alright, so we’re entering cinematic mode now, guys. 

Fighter: Can I use Second Wind, then?

DM: Sure, no problem, it’s just a bonus action anyway. Alright, so Klauth says… [Klauth tries to convince the characters that they can’t defeat it and offers to have the characters become its underlings instead of continuing the fight].

Bard: [Negotiates with Klauth, appearing interested in the offer while trying to learn more about the dragon’s plans].

Rogue: I’d like to apply poison to my daggers while they’re yapping.

DM: You’ll need to roll a Sleight of Hand-check then, but hold on just a minute. [Klauth continues its discussion with the party until it becomes clear that it won’t lead anywhere. The DM is now ready for cinematic mode to end]. Alright, give me a Sleight of Hand check, Rogue.

Rogue: That’ll be… [rolling dice]… 27.

DM: You’ve managed to apply poison while the dragon was speaking, without it noticing. But… [rolling dice]… the dragon hasn’t been idle itself. While talking, it’s been stealthily attempting to procure another wand from the piles of treasure around it, but you notice it, Bard.

Bard: Well, I’d like to start casting a spell, then.

DM: Alright, cinematic mode is over, we’re back in action, guys.

As you can see, the only difference between cinematic mode and regular play, is that you’ve established the parameters clearly to the players and you maintain control of how long cinematic mode goes on for. This ensures that the characters (including the villain) can still do what they’d normally try to do during such a moment – turn it into a tactical advantage – but without them interrupting the dramatic moment before you’re ready.

Not all drama is created during cinematic scenes, however. Often, the drama is most palpable at that final moment, where the heroes manage to claim victory from the brink of defeat – the final roll of the dice, the last strike, the encounter’s epic climax. Now, your boss encounter may not always have such a moment – sometimes the dice simply doesn’t fall that way – but there are some ways you can make it more likely:

  • Make the encounter difficult and dynamic, so that the final moment feels well-deserved and comes at the end of an exciting encounter (see the above advice).
  • Let the players know that it’s coming by describing how wounded or badly hurt the villain is, increasing their tension and excitement – and ensuring they don’t give up and flee when they’re close to victory.
  • If it doesn’t change the outcome of the encounter, don’t hesitate to peel away the villain’s last 10 hit points so that it’s the paladin’s epically described critical hit that kills it, instead of dragging the fight out for a round longer and having it end at a less epic moment.

In addition, when that moment comes, you can make sure that it is as satisfying and dramatic as possible, by:

  • Allowing the players to describe the final moment (I.E. the infamous “How do you wanna do this?”) and/or having a vivid description of the villain’s death ready.
  • Not continuing the fight afterward, if you don’t have to – the villain’s minions slink away, surrender, or are defeated off-screen, instead of prolonging the encounter and diminishing the effect of its awesome conclusion.


In brief summary, this article has laid out some ways to make boss encounters more difficultdynamic, and dramatic, by:

  • Balancing the encounter by improving the boss monster’s action economy, making quick calculations, and using difficulty dials.
  • Making the encounter more exciting by giving the boss monster extra action options and adding extra effects and/or goals to the encounter scenario.
  • Adding drama by using cinematic mode and ensuring an epic conclusion to the encounter.

In the end, however, everything in this article is only advice – and even if you follow it, things might not turn out as expected. And that’s okay, too. All boss encounters don’t have to live up to the exact expectations of what a boss encounter should be. In fact, sometimes it’s alright to let expectations be damned and allow things to happen, even if it isn’t exactly what you had in mind.

Both myself and my players fondly remember how the encounter with the big, evil efreeti villain I’d build up for several sessions ended on the first turn of the first round, as the efreeti spectacularly failed its saving throw against the sorcerer’s newly acquired banishment spell, sending it instantly back to the Elemental Plane of Fire.

Sure, we didn’t get the epic, multi-round, back-and-forth encounter I had planned out, but we did laugh a lot – and still do, whenever we talk about it.

And, that – having fun – is, after all, the most important thing to remember, when playing D&D. So that’ll be my final and most important piece of advice for running boss encounters: however you run it, if everyone’s having fun, you’re doing it right.

A big thank you to our generous patrons at, who support us in creating more articles like this – and helped decide the topic for this article!

J. A. Valeur

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