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

The Soloist

AD&D 1e.

End of the campaign battle against the cleric boss of a red dragon-worshipping cult. Dragon was killed in the previous session. The boss and his elite guards want to kill the characters. Everyone is dying at -X HP, except our fighter and the boss. The fighter has at 4 HPs.

The DM thinks it will be a TPK and has no problem with that since it was a great campaign. The evil boss is laughing at us.

Roll initiative, the fighter goes first. The player gets up raises his hands above his head like he is holding a sword and says 'Excalibur I call on your power' and rolls the d20. 20, it is a vorpal sword. The head of the boss is separated from his shoulders. We win! Everyone is jumping around the room and laughing, even the DM who can't believe it.

Best campaign ending ever.

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He'll flip ya...Flip ya for real...
Im seeing a bit of commentary on action economy. I do really like PF2s three actions and the system built around it. Though, the level systems math is really what makes solos work in a way they struggle in other systems. Mainly its that the solo is able to shrug off your biggest bangs. Meaning the top spells and abilities wont work because the boss can save against them easily. It forces a team work in that lesser spells that provide useful riders help other party members whittle away at the boss until they are defeated.

For some the tactical application and forced team work is a feature. For folks that like to save their big bang for the big boss, its a bug.

James Gasik

We don't talk about Pun-Pun
I'm now going to share the ABSOLUTE WORST BOSS FIGHT EVER*. D&D 4e. DM has us mow through a temple of evil cultists with very annoying powers (like At-Will Domination) and has us face their leader, the vampire-like cult leader who is bound to a tree that is fed on blood.

His mobility is somewhat limited as he has to remained attached to a branch of the tree, which we ruthlessly exploit, and after exhausting our Daily powers, he goes down.

Now at this point I need to interject something- previously, we had to gather pieces of this weapon that had been scattered across the land and we were told it was necessary to "destroy the root", ie, the tree and the cultists.

This weapon was actually several other weapons. When finding another piece, you could have the pieces you have merge with that one or vice versa (letting you choose the form of the weapon- in my case, I was a Halfling so I had it as a short sword) and the final weapon has all the powers of it's components. So at this point, it's a +3 Short Sword. It has two powers of relevance here. 1, it and whoever wields it are absolutely immune to any form of scrying or divination. 2, wounds it inflicts cannot be healed- something which never comes up.

Upon falling, the tree absorbs the leader and goes One-Winged Angel on us, as the DM announces his second form. We have nothing for resources and had no opportunity to take a short rest.

"Because he now has full hit points in his new form, I'll let you all recover a single Encounter power", the DM states, ever so magnanimously.

"Hey, uh, about that. The legendary sword, it means he can't heal, right? So does that have an effect?"

The DM flounders for a bit, reading his notes. "Ah no, he's not healing, it's an entirely new form." Right.

So he found this stat block online, a conversion of a Wormskull Horror from Earthdawn. Mm, homebrew, that could be trouble. And it's nasty. It gives us all a mystical Mark. I ask what that does, and he hands me a notecard.

"Creatures marked by the Horror can be scryed upon freely for a year and a day; the Horror can use a creature marked by it as the source of any of it's powers". Ok, that's really not good.

The creature also has some other odd powers like "Corrupt Karma", where if you spend an Action Point, it can curse you, an At-Will Interrupt where it can simply make another At-Will power do nothing (remember, at this point, At-Wills is pretty much all we have), and an At-Will Dominate (of course).

The Sorcerer gets Dominated into attacking the Ranger, and he rolls a critical hit. He's an Elementalist Sorcerer and hadn't yet used his Encounter that lets him increase his damage. The DM decides "oh yeah, you have to use that too". Erases the Ranger.

It's getting down to the wire and soon I'm basically the last one left standing. It's dazed so it can't use it's goofy interrupt. I attack and roll a 20, thinking, thank the dice Gods, it should die now and we'll succeed."

The DM says "nope, it has hit points left", and it then kills me. That's it, TPK, game over.

Naturally, we're all steamed. "Well, you weren't supposed to fight it, you were supposed to run away. I don't know why you all just kept trying to win."

"One, this wasn't telegraphed to us at all that it was unbeatable. I mean, we have the legendary weapon, right?"

"Oh well, there's still 2 more pieces to find."

"And two, we couldn't run."

"Huh, why?"

"You made it so that anywhere we go, for the next year, this thing can attack us with it's powers. And it can attack anyone nearby it with it's powers, making us a threat to anyone we come into contact with. So what, our option is to run and go hide in a cave for a year and hope it doesn't just kill us at will?"

" wouldn't do that. Besides, it can't scry on you, that's why you have the sword!" The DM replies.

"He can't scry on ME, yes. Nothing about the sword prevents him from scrying on anyone else. So we had to fight, and you saying it wouldn't abuse it's bs power doesn't mean anything to our characters. If you wanted us to feel like we could run, you should have altered the power or not used it."

"Well, I mean, this boss is super important to the storyline, I couldn't let you kill it now anyways."

"Oh so instead, to save your oh-so-precious story boss, you killed all the player characters. Well have fun with your story." And I stood up and walked out. And everyone followed me.

There's no real moral here, other than some of the advice I give new DM's. First, the campaign cannot be more important than the players, or you may end up going through many players and run the risk of having no campaign. Two, if you don't want something to happen, don't let it be a possibility. If you don't want your super cool BBEG to die early, or to have the players TPK, don't put them in a situation where they fight each other! Have the BBEG teleport away cheaply or something, lol.

*I have no doubt others will say they have experienced worse, and it's probably true. But this was the lowest point for everyone who was at that table.

Lat time I was DM (this past summer) I designed a two part "Boss Fight." The 6-7 PCs were eighth level.

It revolved around a Abyss vs Hell scenario. The PCs were trying to stop a hellish portal from infecting the land. (The entire area was sought after because of its ease of interdimensional travel - hence why demons and devils were fighting over the desert land. One side had a Lamia trying to open a portal to the Abyss, and the other a tiefling, trying to open a portal to Hell.

The Setup
The PCs had to make their way to a mine through a canyon or they could have entered through a secret cave in a dragon graveyard. They went the canyon route. After the canyon, they entered the mine. There, they encountered a boss.
The Good
The canyon fight went great! Some imps (used the Magmin stat block) as a distraction. A couple bearded devils on top of the canyon walls (forcing skill checks to get to them for some PCs, and allowing ranged attacks). And two Bone Devils, one blocking the entrance to the mine and the other flying from behind to surprise the PCs. The canyon. The enemies. The rear attack bone devil. The player feedback was solid.
The mine that housed the portal and tiefling had some good elements. It started with four separate trap encounters. They were solid, revolved around the theme of hell and a mine. And the PCs handled them well - as was expected. (They were already hurt from the canyon fight).
The Bad
There was another fight leading to the mine, a pack of hell hounds. It was supposed to be in addition to the other encounters. They defeated the hell hounds, and two of the PCs had built an escape to rest with the lamia that I had not thought of. Therefore, they did that and then travelled to the mine. And despite the time function placed on the Hellish portal, it seemed inappropriate to punish clever play, especially clever play from five sessions ago.

The mine big bad boss fight had some problems as well. The tiefling was using the portal and the arcane structure to create a Nightmare. He had cut off the wings of the trapped Pegasus, and was in the process of the ritual. The PCs were supposed to encounter that and use resources to stop it. They didn't. I did not make it clear. They were on the hunt for the tiefling and ignored everything else - including one side room with a great trap! ;)

In the final fight, the tiefling had a grip on a switch that would cave in the mine (There is a backstory to this; it is how his parents died.). This switch was like an old electricity switch, but it controlled gears that would collapse the mine. It was designed so the tiefling could appeal to the group and explain how the Lamia was actually more evil, and that this frontier land needed lawfulness. He also had an eighth level paladin, one of the players, that was a paladin of Asmodeus. This was a secret. I mean the player let out hints, and it was such a short campaign, it never would have upset anyone, as it wasn't from left field. But one player caught on, and dimensioned door the paladin 500' above the mine. They had an epic aerial battle.

The ranger/archer instantly destroyed the cave-in lever. He shot an arrow at it. I said there is a 10% chance it destroys it. He rolled, after hitting, a 98%. So the cave in was destroyed. They defeated the tiefling no problem. Like, they weren't even in danger.
(Now the aerial battle was incredible.)

So my faults were having a trap in a room that meant nothing, not having the Nightmare ritual have an effect (I wrote it, and the ritual did not finish until the next day after the PCs arrived - so I stuck to that), and doing the stupid cave-in lever.
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Here's a disaster of a boss fight followed up by epic-ness:

During 4e days, WotC published a 4e version of Tomb of Horrors. I think they gave it to us FLGSes as a Game Day thing? At any rate, my friend and employee ran it for us by-the-book. The Demilich Acererak, as statted there, was an absolute CHORE to fight. 1) It took 20 or so rounds to beat him; 2) During which time he did a LOT of STUN attacks; 3) BUT, he didn't do much damage, so we never actually felt threatened by him; AND 4) I rolled below a 10 the entire 20 rounds, except on one non-consequential check. I don't remember what it was, but it made no difference either way to the fight.

I spent most of that fight wishing I would die. Or at least my character would. It was terrible.

SO... when I went to run it myself for my group, I rebuilt his statblock from the ground-up. 4e monster design was really good, but unfortunately, WotC themselves weren't very good at it until near the end of the edition. One of the first things you needed to do, to make the game fun, was to HALF all monsters HP, and TRIPLE their damage output.

At any rate, to make a long story shorter, I had even built in a whole back-story for Acererak where the PCs playing had time-travelled back to when he was alive, and had actually been tricked into dealing a death-blow to him that turned him from a living Wizard into a Lich. As a living wizard, I made him the "fasted wand-slinger in the Conclave". That fight itself was epic, with him built as a "solo monster" with a massive action economy (5e players think Legendary Actions). That was his living statblock.

In his Demilich form, the gems that had been on the hilts of his wands were now the ones in his eyes, and the skull floated around, spinning in a blast attack (Imagine like a deadly disco-ball shooting lazers, but more badass and evil!) Among other cool things that he was able to do.

The general lesson is: Make monsters die faster, but do more while they are alive. A LOT more. The goal is to have the monster die right at the point that the players no longer think that they're going to win. "We're screwed; Oh wait, we won!" is infinitely better than, "We're gonna win eventually - but it sure is a slog."
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