Tell me about your Bossfights! What went right, what went wrong?


of the Longing Mound
So recently I started a TTRPG blog, Longing Mound, where I want to study some design things. And one of my first quest is gonna be a quest for elusive Good Bossfight.

And now I want to collect some data about people's experience with the subject! For research.

So, tell me about your bossfights! Bossfights you designed as a GM! Bossfights taken straight from published adventures! Bossfights you fought through as a Player!

What went right? What flopped hard? Anything particularly interesting to mention that is neither? Was it high concept, was it about about the earthly Math? Any specific pain points worth mentioning?

The Mound longs for all sorts of knowledge from your practice! And thank you for your time either way.

( also should I make copies of this thread in the specific games sections? I am new here so I worry this might be against the rules to make multiple identical threads, but I would like more Data )

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In 5E, the fight goes better if the BBEG has a bunch of minions. Otherwise, they will be defeated quickly by the party's superior action economy.

If that's not an option, then fights will go better if the BBEG's HP and AC are materially buffed, has at least 1 powerful magic item, and the lair has plenty of traps and lair actions.


Not your screen monkey (he/him)
Two of the hardest things to deal with are the action economy of multiple players vs a BBEG and initiative rolls. And yes, this is based on experiences (from last night, in fact).

1) Action economy: Legendary Actions, lair actions, and minions help deal with this issue but they don't necessarily keep a well-equipped party from concentrating on the BBEG if they're in the same adventuring space. And even those action economy adjusters are potentially hindered by the second, which is a matter of luck more than encounter design.

2) Unlucky initiative: If your BBEG and, worse, minions end up going late in the round compared to the PCs, even using legendary actions and a lair action can leave you with a BBEG badly pounded on by all of the PCs concentrating on him rather than the weaker minions before he even has his proper action (hope those legendary actions give him some fun things to do). This is one area where a PC group's fighter, yes fighter, can shine. A higher initiative than the BBEG and a decent attack that can be brought to bear, and that fighter can get two full actions worth of attacks on that BBEG thanks to his action surge. And if he's a battle master, he may have been able to trigger high value attacks from his fellow PCs, such as the rogue. Yes, he's nova-ing on that first turn, but it's probably worth it because it can leave a BBEG badly mauled right out of the gate.

James Gasik

We don't talk about Pun-Pun
So things I've noticed.

1- as stated, action economy. You can load up someone with all sorts of "cheats" like immunities, resistances, legendary actions, lair actions, whatever, but at the end of the fight, it will come down to the fact that 4 guys beating up one guy is a losing proposition, since, unlike in movies, your opponents don't attack you one at a time hoping that works.

2- the more fiddly the BBEG, the worse it gets if you add more foes. In the past 2 sessions, we were fighting a Lich and 16 Wights. The Lich (being a Cleric type) had Legendary actions like the ability to cast Sacred Flame at the start of an enemy's turn, but as the fight wore on, the DM kept forgetting about it.

3- what I've learned is that it's best to not only use multiple foes, but subvert expectations. The obvious BBEG shouldn't be the toughest thing on the field! Either have a "secret BBEG" or give them a Dragon (not necessarily an actual Dragon)- a nasty enforcer who does all the dirty work.

I ran a really neat boss fight once where the actual bad guy was just this noble (I gave him the ability to shout orders in combat for some Warlord-style action. Bonus actions, movement, bonuses to rolls, that sort of thing), but the most dangerous foe was the leader of his personal guard.

2e's Dragon Mountain does something neat along these lines- you finally get to the Dragon's lair, and see her in all her glory, so the party unloads on her...but oops!

It was just a Kobold polymorphed into a dragon! The real dragon was hanging out polymorphed as a small bird!

Now the real fight begins!

2e's Dragon Mountain does something neat along these lines- you finally get to the Dragon's lair, and see her in all her glory, so the party unloads on her...but oops!

It was just a Kobold polymorphed into a dragon! The real dragon was hanging out polymorphed as a small bird!

Now the real fight begins!
that's not an oops, that's effectively two dragons plus a kobold. Which is fine, they didn't know there were two dragons and it's a good trick. But for all the existential handwaiving, the encounter is a dragon, a hidden dragon and a kobold that pops out when the first dragon falls.

Something you need to do is consider what the party's top 2 tactics are and be prepared for them. Which is NOT the same as nerfing them. Let's be clear, one trick ponies need to run into their kryptonite occasionally (an army of blind morlocks in the land of the mole people ignore the Medusa head artifact) but not frequently.

What I mean is as a gm be prepared for the BBEG to be flummoxed without the GM getting flummoxed. You don't the whole game can come to a halt or the encounter go off the rails because you lose your train of thought.

If the PCs latest favorite tactic is to use Mental Prison on the BBEG, what will the BBEG do while panicked and blind? Can they erect a Force Cage as defense? Will they go defensive? Will they try to teleport out, taking the damage? Are they yelling to their minions?

What do any minions do? How will they react to BBEG being freaked out and seemingly detached from reality?

And even if that's not what happens, the act of thinking about what might happen when the PCs gets the upper hand will help you deal with whatever fresh chaos they unleash. Just remember it's okay for an NPC to be gobsmacked, just keep the game moving.

Boss fights have to be powerful enough to challenge the party. One side can be forcing a long attrition (aka a lot of hp), alternately the bbeg can be nearly unhittable (AC 90), you could have chaff (minions), some environmental constraint that limits the number of attackers, or some event that keeps some PCs out of the fight, like a Temple-of-Doom-esque cage of orphans being slowly lowered into lava.

There is one other option to make a boss fight more difficult: make it a series of battles. Have the bbeg run away. If the high priest has a Blur effect the whole fight and retreats, can the PCs recognize them in a mob of lesser priests if they ditch the giant pointy hat and turn off the blur?

If it takes 10 minutes to catch the bbeg, the party's buff spells are gone. Trap doors, secret passages, a rope & counterweight, a bodyguard that literally carry them out of combat (a giant bird maybe), a potion of water breathing and an underwater tunnel plus just enough minions to keep the party from resting and a few simple traps that keep them from blindly charging forward without arriving at the fight bloodied.

In the outdoors, never underestimate two or three sneaky npcs with longbows or heavy crossbows to slow a party down. They can snipe at long range from total concealment (which counters the long range disadvantage), blocking rest and irritating the PCs. Especially the unarmored wizard you keep shooting. Add a hunting horn to make the PCs paranoid.

Underground or indoors, be prepared to be irritating. Think filling hallways with smoke. Not magic smoke, just smoke. A couple bundles of grass thrown on a fire. You're buying time, not going for the kill.

You could give the NPC a small cache of expendables at each fight. They aren't carrying twelve potions of healing, but there are four in each cache (good for 84hp in total). This one has a potion of water breathing near a canal, that one has a potion of fire breathing in a cotton warehouse, the last one has a featherfall-token and a window to a sheer 60ft cliff and a river...assuming the water breathing potion is still working.


of the Longing Mound
Thank ya'll for your posts!

I am sorry for being unclear in the original post. This is not really meant to be a "I want advice on bossfights" sort of a thread (not that I don't appreciate these). What I seek first and foremost are your stories from the trenches!

Tell me about how your coolest bossfights went, as a GM or as a Player (or about how they fell apart)!
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A Title Much Cooler Than Anything on the Old Site
Hi, a topic close to my heart. I feel this is perhaps my greatest weakness as a DM. People will always give advice on how DMs control the world and should know the PCs and and players and their abilities. But what is often overlooked in these discussions is that when running games for very experienced, tactical players, 4-6 heads are better than one. I often find that that side battles and random things that happen on the way to the boss battle are more interesting. I feel in my games the enjoyment is more from the journey along the way to get to the boss battle, than the boss battle itself. I'll give three examples of campaign ending boss battles.

First D&D 5e campaign, and first TTRPG game a ran in over 20 years, having been out of the hobby since the very early 90s.

It was a 1-20 level homebrew campaign in a homebrew world. It was a dracolich with a number of powerful caster minions, a Rakshasa and a good number of mooks. None of the party went down. They did feel seriously threatened at the start of the battle, but after some good tactical choices and good roles it quickly back apparant that the battle would go their way. I don't recall many of the details of it because it just didn't stand out as one of the highlights of the campaign, which bothered me at the time. I remember it being an exhausting combat to run and that 20th level D&D players just had so much power that it was difficult to plan a challenge (at least for me at that time).

My next campaign was Curse of Strahd. I needed a break from homebrew and creating everything myself and I really like Curse of Strahd. It was a great campaign, except for the final confrontation with Strahd. Where I perhaps went wrong is my strong desire to run it it as written. I place Strahd according to the Taraka divination at the start of the adventure. The players had found the model of Castle Ravenloft in the Amber temple. They found a window that they would try to enter from instead of trying to come in through the main entrance. It happened to lead to K88. Tomb of King Barov and Queen Ravenovia, where the Taraka diviniation placed Strahd. So they come crashing in through the window, surprising Strahd and themselves.

The battle itself was intereing leading to an interesting hide & attack sequence through the catacombs. But Strahd had no minions with him and the party was at the upper levels for that adventure and had brought a powerful supporting NPC they had made an ally along the way. The downside was that they never had to make their way through and explore the castle, so I felt I deprived them of one of the main highlights of that adventure and it would have been much more of a challenge if they had to explore the castle and find Strahd. I probably should have just selected another location for Stahd as soon as I knew their plan but that goes against how I like to run my adventures. I roll in the open, don't fudge rolls, and like to let the story emerge from PC actions rather than curate and change the adventure and outcomes unless there is in-world logic to do so.

My last campaign that I wrapped up at the end of last year was a Rappan Athuk campaign that lasted 5 years. I wrote a very lengthy description of it here:

The entire encounter lasted 16 hours. It was a gonzo 20th level D&D encounter. The fact that it played out so long might sound terrible but overall it was fun. I don't think that it was as deadly as it should have been, despite my putting a lot of thought and prep into it. But that was the result of a great deal of planning, which in a sense started five years ago when we started the campaign. The players were rewarded for their years of preparation and accomplishments by turing an unwinnable encounter into one that they were able to win mostly unscathed. There are some decisions I would have made differently, perhaps, but, overall, it was a fitting end to a very long campaign. I go into great detail about it in the above-linked thread.

Our next campaign is Warhammer Fantasy 4e. We are looking at a change for D&D. I also think that WFRP4e does a much better job at keeping combat dangerous at high levels. Even when that players seriously outclass their opponents, the rules of Warhammer make it so that a good or bad roll can seriously f' up a PC and combat should never be entered into lightly.

Hope that is what you are looking for.

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