You'll Never Walk Alone

Why Bosses in D&D Should Not Fight Solo

Treat your bosses better than poor Ralph Wiggum

As someone who occasionally likes watching soccer (what everyone outside the United States calls football), I felt a little pride watching the United States men’s team get its first draw (and second result other than a loss) in 20 matches against powerful Brazil. Sometimes rooting for the underdog is fun!

Then when it came to D&D prep, I thought of the song "You’ll Never Walk Alone." which has become a popular anthem at several football stadiums across the world after starting in Liverpool.

My players are currently hunting down a lich who knows a powerful secret from outside their plane of existence. I’m currently deciding what type of reinforcements the lich has if the party ends up in combat. I know my group. There will be combat. (They know they’re chaisng a lich so this isn’t a spoiler.)

When I read Vecna: Eve Of Ruin, the phase “You’ll Never Walk Alone” kept playing in my head, because so many bosses at the end of various chapters fight alone: Chapter 7, 8, 10, and chapter 6 depending on the party’s approach. Even Vecna fights alone.]

I have never understood this philosophy. When I started writing adventures, one of the first things I learned is to never have the boss fight alone. Here are some of the reasons why:

1) Story Immersion

One of the things that often makes villains a "boss" is their ability to attract and command minions. Think of the evil lord tyrannizing the countryside, a dragon who has claimed the party's stronghold as their new home, or Kas trying to disrupt Vecna's plans. These villains have allies and underlings.

When the party fights the boss, it seems odd if the underlings were all in another room. Lords have a personal guard. Even the most selfish dragon understands that their followers could be useful sacrifices and distractions to soften up the heroes and lock them in place for a devastating breath weapon.

If part of a villain's story is their ability to command followers, some of those followers should be in the final confrontation. Otherwise, it sends players the idea that the villain is actually a weak leader.

2) Initiative

I roll all my dice in the open unless I am DMing for level 1 or 2 characters, where I want to fudge the dice in their favor to prevent a random critical hit from killing a character. That means if my solo boss rolls a 3 or a 1 on initiative, they may go after the entire party.

The last time I DMed with a solo boss was a pre-written adventure for a charity event back in 2020. My level 12 party was fighting a zaratan, a massive CR 22 earth elemental. I rolled a 1 on initiative and with a +0, that's still a 1! My the time my turn came around, the party had dealt the 307 damage needed to kill the zaratan as written. I fudged the monster's hit points to keep my players entertained as they had donated to charity for a seat at the table. After two rounds I couldn't maintain the illusion anymore. (I will talk about the merits and demerits of CR in a later post. I don't think anyone who has taught statistics and quantitative methods has ever looked under the hood to try and explain it before and there’s a lot that is misunderstood about how CR works.)

A boss who fights alone is much less of a threat if they roll badly on initiative.

Conversely, some of the things that go into constructing a solo boss make them a much bigger threat if they go first. During a convention last month, the boss for a level 20 adventure was an ancient sapphire dragon. His breath weapon can incapacitate a character for a round if they fail a DC 23 Constitution saving throw. If the dragon goes first, no one in the party has a chance to move out of the way of his cone.¹

A DM who rolls behind a screen can alter the die rolls to even out the luck (and probably should). In convention play, I tend to fudge boss fight initiative rolls a bit to get bosses to act closer to the middle of the initiative order and I’ve yet to have a player complain. However, we cannot base design in a dice game on rolling behind a screen and altering the dice.

3) Monsters Have Limited Actions

Each monster only has one action. They tend to make multiple attacks or have a bigger ability they can use like dragon's breath, but that's only one action. Boss type monsters also get Legendary Actions or maybe Reactions to be able to do things outside of their turn. However, it's extremely rare to give a monster both Legendary Actions and Reactions for good reason: it can be too much for a DM to remember.

By the same logic, there's no monster who can do everything. For example, let's look at Vecna. He has some abilities that can target multiple characters and a melee attack, but he can't sit back and throw death bolts as ranged attack rolls. Conversely, Orcus can attack with the Wand of Orcus or throw death bolts, but he doesn't have a special area of effect damaging ability.

The easiest way to add to a repertoire of what a boss can do is give them minions who do things the boss can't. For that ancient sapphire dragon fight, I needed more consistent damage dealers, so I added a death giant shrouded one and two drow inquisitors. Both rely on attack rolls, can be run fairly quickly, and the inquisitor gives a bit of utility if needed. For some parties I used a death knight instead.

If I was designing Vecna, I'd give up on the idea of him being in melee when there are so many undead minions who could fight as melee bruisers.

4) Solo Monsters Are Disruptable

This is the biggest reason optimizers say not to use a solo boss: almost any monster can be disrupted by one of a few strategies involving a certain character, but it's much harder to disrupt a group. For example:

• Casting hold person against that feudal lord terrorizing the land in a level 3-4 campaign or hold monster in a higher level campaign. Many classes get access to Raluothim’s psychic lance in Fizban’s Treasury of Dragons, which can incapacitate a boss for a round if it fails an intelligence saving throw (a rare save to be good at)

• A monk's Stunning Strike takes away the boss' turn. Monks can try to stun after every attack! (There's a reason this has been limited to once per turn in all 2024 Player's Handbook Unearthed Arcana tests.)

• Grapple the monster so they can't get close enough to attack more vulnerable targets. Few monsters are proficient in Athletics. At higher levels, telekinesis can do restrain the boss and get around Legendary Resistance: I did this to Szass Tam last month.

• At high levels, trap the boss in a forcecage that's completely enclosed or cast maze on them, which doesn’t allow a saving throw and forces an Investigation check (not a save) to get out. Several bosses in Vecna: Eve of Ruin are completely shut down by this strategy.

There are plenty of other things that can be done to a solo boss that involve more strategy. The things listed above are just some of the most common, because they can seem like "I win" buttons for players.

5) Solo Bosses Encourage Frustrating Design

Imagine that the party is fighting Orcus at the end of a long campaign. The monk wins initiative walks up to Orcus, punches him in the stomach, and then Orcus is stunned because he rolls a 1 on his saving throw against Stunning Strike. Is this fun?

I expect reasonable people to disagree on their answer to this question.

For some players, stunning is lots of fun! They want to feel like they could do the big thing to completely shut down the boss. After all, in a real fight, you’d try to incapacitate a deadly opponent as quickly and efficiently as possible.

For game designers and many DMs, this isn't fun. We think of long dramatic fights in the movies. Even if the hero is highly trained and knows how to disable their opponent, they don’t knock everyone out in one hit. That's why D&D has Legendary Resistances, to let bosses and similar monsters pass saving throws they'd otherwise fail.

As you might imagine, Legendary Resistances are the bane of players who want to completely shut the boss down as quickly as possible.

I feel like trying to immediately stun or hold the boss is fundamentally a lose-lose proposition, because either the player or DM is going to walk away disappointed. One good compromise is to design boss fights with a somewhat weaker boss but noteworthy second in command who doesn't have Legendary Resistance and is an ideal target for these effects.

Another good compromise in the design of specific monsters was found in Flee! Mortals, where using the equivalent of Legendary Resistance comes at a significant cost for the boss monster.

Newer WotC Bosses Add Frustration

WotC's recent boss monsters have gone in a different direction: trying to “even the odds” by taking away player's turns. Whether it is the false lich knocking everyone within 30 feet unconscious, Vecna countering three spells per turn with unlimited range and teleporting away from melee combatants in the middle of their multiattack, or all the stunning from Phandelver and Below, denying player turns seems to be a new emphasis in WotC monster design. We also see this trend in monsters who aren't bosses.

These monster designs are just as problematic as Legendary Resistance if not more so. If players know Legendary Resistance exists, they can start to guess which monsters have it and devise alternate solutions. My level 10 bard/warlock Ellywick likes using Raulothim's psychic lance as their biggest spell to incapacitate a creature for a turn if it fails an Intelligence saving throw. If I see a boss likely to have Legendary Resistance, I can have Ellywick cast plant growth to restrict their mobility or cast hex and eldritch blast.

Now imagine Ellywick is level 20, facing Vecna. They've got lots of spells as they keep taking levels in bard. However, Vecna can counterspell three times per round and there's no way to escape it. If Vecna rolls high enough on an Intelligence check to counter high level spells, then Ellywick can't do anything no matter how I play. In my first post on Venca: Eve of Ruin, I mentioned how Ellywick can't recover from the false lich's mass stun.

In a game where high level play involves counterspells three times per round that can't be countered back, Ellywick becomes much less fun to play. In a game where high level combat means high DC save or suck attacks that deny multiple turns, Ellywick is an inherently doomed character, fun until not being able to do anything in these boss fights. There's nothing Ellywick can do to overcome these save or suck abilities, no matter how well I play.

Adapting To Save Or Suck

I know that some game designers love the idea of save or suck abilities to try and limit powerful characters by taking away players’ turns. Sometimes I will just refuse to play their adventures if they are excessive in the use of save or suck or do things like a DC 27 psychic scream, stunning anyone who fails that Intelligence saving throw until they repeat that save at the end of their turn.

If I knew I was going to play Vecna: Eve of Ruin, I’d make sure to play a character with proficiency in Constitution saving throws and get Resilient: Wisdom by level 16, or start with proficiency in Wisdom saving throws and get Resilient: Constitution. When designers love monster abilities to potentially take away multiple turns, Resilient becomes a feat tax that you have to take to make sure you don’t lose turns and sit watching others play.

The irony is that if a player emphasizes the saving throws they really need to succeed, they have a good chance of beating the save or suck design. My level 16 paladin Laucian is optimized for this type of design with a +6 Aura of Protection and +10 or more to four saves. My level 20 artificer has +21 to Constitution saving throws and _19 to Wisdom saving throws. He is almost always going to get his turn, but artificers don’t get as much to do on their turn as many classes. When boss combat design emphasizes save or lose your turn effects, players adapt at the cost of certain character options,, and everyone loses.

Solution: Take The Boss Down a Notch, Add Minions

Go back to that zaratan fight. In my own adventures at that level, I downshifted to an amnizu but with several minions. Or instead of the false lich's turn denial, use a normal lich (possibly with some spells already used) and minions. The Monster Manual lich has far fewer hit points so it needs minions to survive a fight.

At level 13-16, I could have had players fight an ancient dragon on its own and most parties would survive. Instead of doing that, I made an adult dragon the default and added devils. Along with helping with mechanical and game design issues, it stood out as a story element that these dragons made a deal with devils. Here are some rules of thumb I use:

• When bosses have some complexity in their combat options, use minions who make attack rolls and do enough damage that the party can’t just ignore them.

• Having a second monster type who has a few combat options can be nice for a fight of boss, lieutenant, lackeys. This assumes 5-6 players.

• I try to avoid using more than three stat blocks in any fight, as cognitive load increases exponentially after three.

• I also tend to prefer fights where there are more PCs than monsters. Even though I tend to be pretty quick with my lackey’s turns, it can really be a drag if players have to watch a dozen monsters attack.

• With only 3-4 monsters, I roll initiative separately for each. Boss fights where all monsters of a certain type go at once can swing against players.

1. The ancient sapphire dragon is fairly weak outside of its breath weapon, as its melee attacks do terrible damage. This makes the incapacitation for a round survivable unless I recharge the breath weapon a second and third time in 4 round of combat, which I did one game.