What's the toughest fight you've ever run (intentionally)

[Monkeyknuckles]

What's the toughest fight you've ever run? What's the hardest you've ever pushed your group in order to make them think outside the box? What's the one fight that stands out where you threw something diabolical at the parties greatest weak point? (try to avoid unintentionally overpowered encounters, like when my old DM threw 2 dire-bears against a lvl 2 party)

Mine was during an e6 game; the players were level 6+8 feats,and were trying to rescue the king of the human nation from a cannibal pirate queen: The Bloody Miss.

After boarding her ship and waltzing through several waves of non-threatening mooks, the party walked into an ambush, got beaten into negatives multiple times by the Bloody Miss (who was a monk/factotum setup to run exclusively off her massive Int score) and her lieutenants. They could only hit her non Flatfooted ac on a 20,and her saves were so high she could only fail on a 1. This encounter was designed to encourage the players to include an arcane caster as a character (Lack of pc's meant I allowed and encouraged the players to run two characters.) So after *13* rounds of combat vs The Bloody Miss and her lieutenants, they finally beat her by using an astral construct to suicide rush her with a portable hole in one hand and a bag of holding in the other and had to suck her through a hole in the universe in order to win. Prior to dying to this attack the players had hit her *once* for 1d6.

[Alcore]

An encounter in Pathfinder's Reign of Winter. It was a pbp that fell apart shortly after starting.


the setup;
Party was attacking a log cabin with a small mob of CR1/2 mooks guarding it. The bandits were forewarned of the parties arrival by a mook from a previous encounter. He survive and when he came to limped back to base. They were all inside with the door and windows bared.

what happened;
I described the party atop the hill overlooking the cabin some fifty feet or more away. Night had fallen but it was dim lighting due to snow. round 1 meatshield B (also healbot), archer, mage charges down the slop. Bandits open fire through arrow slits when in range. Meatshield A tries diplomacy, from 50+ feet away, in a light snow flurry, through a battle, and a wall of wood. i didn't bother rolling.

Round 2 they reach the door and begin hammering. Party takes damage but bandits don't. Meatshield A continues diplomacy (i tell her again they can't hear). She starts down the hill. I smash my head against desk.

Round 4 mage is running out of options, healbot running out of healing. Bandits remain untouched. Someone gets the bright idea to smash in the windows.

Round 5 a window is smashed. Mage who posted last used color spray, party finally outnumbers the bandits in question. Friendly fire claims archer (he was in the cone). The rest approach 0hp (except meatshield A).

Round 7 they win. They have 3 more encounters and despite them hearing the battle i pull an 'artificial stupidity' card from my hat. Party has no healing left, no spells and they luckily recieved no extra damage since round 5. Party retreats. Game falls apart.


A seige, they tried to seige.

Thank god i didn't use my head.

[BWR]

Tiamat, post Red Hand of Doom.
Our original group of PCs wiped, and since the DM had adapted RHoD to work in Mystara, set not far off where one of our main PCs had a domain, I used the failure to run a brief encounter with the PCs of the main campaign. Since the main party was all 16-17th level they would have stomped the encounters as written, so I buffed Tiamat a bit.
Long story short, six PC deaths spread amongst four PCs, a near wipe and much of the countryside ruined, along with the death of a well liked NPC.

[Florian]

Village under siege type scenario with a timer to the invasion event. Basically, the group had around one week to make alliances and try to whittle down parts of the enemy forces while those did their own prep. They spectacularly failed at both tasks and wasted the whole week depleting their resources.

So I decided to start the invasion event with the full force, main army as well as all encounters they managed not not kill, defeat or drive of in the time they had.

All in all, 5 level 6 characters vs. 20x gnolls, 20x goblins, around 10x gnolls and goblins with class levels up to 8th, 10x lvl 5 Zentarim Phalanx Fighters and one 10th Zentarim Mage flying a Wyvern.

Spectacular battle. When the dust settled, 2 of the PC were actually still alive.

[Talverin]

Group of six players in my first 5e game. They were supposed to steal some (already stolen) goods from a warehouse belonging to a local criminal cartel. Two entrances, four guys on the rooftop with heavy crossbows, six guys inside. Party members were level 3. Well, they all walked right the **** up to the warehouse with weapons drawn and came under fire from the crossbow-wielding rooftop dudes. They stood out in the open and tried to fight back at the crossbow guys (Who had height advantage) while the melee characters charged the door... Well, the rogue decided to hare off around the back of the building solo, and the front door was locked, so the melee characters spent some time smashing on the front door (Giving everyone inside time to pile up into a killing zone) while the crossbow guys... well. The wizard died. The party had a really rough go of it. The rogue unlocked the back door, getting into the room with the bandit leader and his two guards, who were supposed to flee when the party broke through. Rogue panicked... and closed the door. They locked it. Next round, the rogue unlocked the door again, and tried to sneak in...

... sneak into a room with three armed people in it, who knew very well that he was trying to sneak back in. He got pummeled. Hard. Knocked out in one round and left alive 'as a warning'.

End result? Two of six dead, one seriously wounded, and they ended up panicking and lighting the warehouse on fire because they didn't think they could win the encounter.

Mission failure.

[emulord]

I was running an alice in wonderland campaign (Dungeonland).

There was a wall they needed to cross "guarded" by Humpty Dumpty. Humpty Dumpty just insults them but has no ranged abilities whatsoever. They just have to find the hidden door or use grappling hooks or whatever. They get pissed off and the hobbit ranged weapons master throws a rock, causing HD to fall and splat on the ground.

This summons "All the kings horses and all the kings men"
60 frost giants mounted on dire rhinoceroses. This is BY THE BOOK. Needless to say the players surrendered which advanced the plot :)

They were level 9. The CR of that battle is something like 22

[Hackulator]

Was running a CR 20 (to start) evil monster game that was in the future from an epic good game I had run. Party gets orders to go kill a semi-retired champion of good and to "get his damn pet too."

Optimization was very low for what they were, though still incredibly powerful as they were epic monsters.

Party was:
Storm Giant Fighter
Lich (can't remember if sorc or wiz)
Astral Stalker Rogue
Half-Fiend Elder Brain of Thoon

They get gated near this small log cabin, use various abilities to spy on the person inside and see an older man in a robe reading a book with a large dog sitting at his feet. Party determines that they are about to fight some powerful wizard or druid with a familiar/animal companion, prep for that fight and attack.

Dog returns to its normal form, an epic Hound Archon Paladin. Man returns to his normal form, a Great Wyrm Bronze Dragon. One of the players goes "Oh **** this is me" because he recognizes his character from the earlier epic good game, an Ubercharging paladin.

Party proceeds to get TROUNCED, barely manages to survive, Lich gets kicked back to his phylactery.

Get back to the NPC running them at the time, are pretty mad, he's like "yeah I just sent you after him to see if you were smart enough to run away."

[Calthropstu]

This is a 2x tie.
The first was a party of 4 people. It was a 1 time game and they challenged me to kill them. I allowed them to use any 3.5 source. They all took half trolls... and no rogue.
First I had a trap that dropped half the party into a spiked pit, with people pouring out of a hidden path on both sides. The fight went their way, but it was dicey. The REAL problem was the fight alerted everyone in the stronghold.
When they got to the next room, 50 firey xbow bolts backed with truesight from lvl 1 archers backed with a pair of fireballs wiped them out.
The second was a part vs party fight. I had a mage backed with 2x fighters. The mage opened with black tentacles, and the fighters bullrushed anyone who got past using readied actions. Near party wipe, but they all survived by retreating, and then firing through the tentacles. What followed was a 10 round fire fight.

[molten_dragon]

It was during book 2 of the Iron Gods adventure path. The party was around 7th level, and made a really stupid decision to sleep inside the dungeon they were in. I even said "Are you guys sure?"

I guess they figured they were safe because they were in a locked room inside a rope trick.

When they woke up and opened the door, they found every remaining monster in the room directly outside the room they were in, all of them behind cover, buffed, and with readied actions. The fight was with something like 6 dark slayers, 6 dark creepers, a dark stalker, a xill sorcerer, An ettin, half a dozen robots of various types, and the dungeon's big bad an advanced arachnid robot with 4 mythic ranks. It was a complete TPK. The only one I've ever run.

[Quertus]

Hmmm... I'm still working on an answer to the question asked; for now, I'll answer the toughest fight I never ran.

I set up a character to be the BBEG of the campaign.

This black-robed wizard offered to pay the party casters orders of magnitude more than the going rate for spell casting services at a set time and place. He probably also offered the non casters some amount to be there to safeguard their caster allies.

When the date drew close, he checked back in on the party, to confirm that they were still available. When they tried to haggle over price, explaining that they could cast higher level spells now, he countered that those variables could no longer be altered (yes, he was getting them to power an epic spell).

When the day arrived, the party showed up, and found that Numerous NPCs (most of whom they'd never met) had been convinced to help. But they were outnumbered by demons, who were also powering the ritual. The ritual - the third of its like the evil wizard had performed - involved him absorbing the essence of a dead god, in the hopes of attaining divinity.

At the ritual's conclusion, the demons betrayed the black wizard. The party - like most of the NPCs - wisely stayed out of this fight. To the demons' short lived horror, the ritual was a success, and the newly empowered literal god wizard wiped the floor with them.

Now, the god wizard was supposed to become the campaign BBEG, and his NPC allies - who were both more numerous and higher level than the party - were supposed to be an extremely difficult fight, winnable only through superior tactics and careful evaluation of the capabilities of this group (who, knowing exactly what level of spells everyone present could cast, were less concerned about the pc's than some of the higher level NPCs present). Or through recruiting some of the powerful NPCs present to assist in the final battle. Or... well, anything but a direct confrontation.

However, contrary to my expectations, the pc's decided to join forces with the BBEG.

They were a good influence on him, so he didn't turn out quite as evil as I had intended him. So, one could argue that they saved the world by joining the BBEG.

They did, at least, fight a subset of his lieutenants, who were miffed at how much attention this new band was getting. It was a "friendly" duel, with no deaths, so that the old guard could make sure that the pc's were worthy to serve their lord. So I got to have a smaller, more balanced version of the epic battle I'd envisioned, at least. But I'm still curious what that group would have done had they needed to find a way to actually defeat all of the BBEG's forces.