D&D 5E The Hardest Encounters

[Fauchard1520]

As you work your way through GMing a campaign, you add more and more complexity to your encounter design. Venomous critters appear. The orc shaman starts casting spells. Lair actions crop up when you finally meet that baby dragon at the end of the baby dungeon. It’s all cumulative, and it’s all meant to help prepare you for the actual end-boss of GMing: running high-level combat.

So here's my question to the board: What’s the most mechanically complex encounter you’ve run? Were you its equal, or did you find yourself overwhelmed by all the rules and options? Any way to combat getting bogged down in complexity?

(Comic for illustrative purposes.)

 

[iserith]

It's not particularly complex per se, but when the DM sets up an encounter that is going to involve monsterbating (i.e. having monsters attack other monsters), it's best to think about how to abstract that out of the normal combat rules so as to avoid a lot of DM-on-DM action that takes away time from the players.

I have otherwise not found high-level play to be complex enough to slow things down even with some of the elaborate set pieces that I'm known to create. The only thing that bogs it down is if the players aren't very familiar with their characters, which is why I don't tend to run high-level one-shots.

 

[DeviousQuail]

I once ran an encounter that took place in a winding canyon against a dao, efreeti, and some elemental minions. This was their third encounter of the day against two CR 11's and a few CR 2s. I don't remember the player's levels but it was a deadly encounter whereas the other two encounters were in the medium to hard range. It was already going to be a lot to track but I designed the map to allow for earth gliding in most places. The only places that were "safe" were the stream and on top of a couple vehicles that the players were trying to take. The efreeti used its fire wall ability to block off the vehicles while throwing flames at anyone that approached. At one point the dao's minions were pushing boulders into the canyon. I didn't even use the dao or efreeti's fly abilities because it was already enough to track everything else on top of the PC shenanigans.

I felt up to the task and it was a pretty fun encounter. I wish I could go back and run it again knowing what I know now. I'm confident I could make it a bit more streamlined.

 

[Baldurs_Underdark]

The show must go on. DMs should never stop to think longer than max. 30 seconds per turn during combat. So, no complexity for me, even at high level.

But I don't consider legendary actions or lair actions particularly complex. And some damage resistance is also not very complicated. The real complicated one is spellcasters with lots of spells at their disposal. As a DM I usually don't know their spell-list by heart, so I need time to play it optimally. That will slow down a game, which I don't allow myself to do... i.e. my answer to the OP's question: I get overwhelmed with too many spellcasters when they all have different spells at their disposal.

 

[Stalker0]

It was the party versus 100 githyanki, 3 battleships, 10 gith warriors, and a gith battle captain.

I made an excel to handle all of the rolling for saves and attacks

 

[Shiroiken]

The most complicated encounters I've run are in 3D, usually underwater. For whatever reason, it's very hard for some players to wrap their mind around it. I think going theater of the mind would be better, as every time I've tried to use minis, it seems to make it worse.

 

[Reynard]

The most frustrated I have ever been running a 5E encounter has always been against a singular big bad. Not because they are complicated, but because they suck. Luckily I eventually learned to redesign "solos" in a way that makes them viable.

 

[M_Natas]

My 6 players were teleported into a Village, that was attacked by an army of undead. So I had my 6 party members, like 6 fighting Villagers who manned the walls, 1000 Zombies and Skeletons, 2 Zombie T-Rex, a skeletal dragon and two homebrewed pseudolichs as the commanders. The players were level 4 or 5 and won by taking out the liches. They were actually only supposed to hold out long enough for reinforcements to arrive. But they did it ... ah yes, in the middle of the fight a small goblin troop on real T-Rexes arrived (helping the players). That was fun but also an exhausting 7 hours of game day.

 

[Stalker0]

I will say in general the most complicated combats involve a lot of types of creatures. Like an ensemble of 6 different monsters is much harder to run than 20 of the same type. This is doubly compounded with spellcasters. 1 spellcaster is always a pain, 2 spellcasters is more than double trying to keep straight who has what spell.

I will also note that creatures with reaction are like 2x-3x more complex than cretures without them, its so damn easy to forget about those reactions!

 

[Ralif Redhammer]

My vote would be either the final battle of Rime of the Frostmaiden or a recent large-scale battle I ran that had multiple regions with different challenges, plus random battlefield events.

Was I their equal? I like to think so, but certainly with the former, which spanned three sessions, I had to take copious and detailed notes.

 

[Oofta]

I frequently run fairly complex encounters, especially now that my group's PCs are in the upper teens. While I almost neve run straight solos, if I have more than 8-10 monsters I'll start looking at the mob rules. Sometimes I'll customize attacks like giving a mob of zombies special overrun capabilities. I also use average damage for everything, sometimes even noting what average crit damage would be.

When I do run boss-type monsters I typically still give them a minion or three. I try to give them interesting things to do and think about how to describe lair actions as preset traps, or non-combatants that pop up/in and trigger things and so on. I will also give the boss monster (I refuse to abbreviate that ) some ability to move around or change the environment to their advantage.

Simple example was my 17th level group against an adult red dragon* and an iron golem. The group was in a somewhat constrained space and the dragon could fly around (and eventually flew away). But as he was breathing fire, he was simultaneous healing his golem buddy and starting fires that he could push people into. It was a tough fight for the group because it wasn't the first (or last) encounter of the day. I could have made it even more difficult if I wanted by having him do things like grab someone fly up as far as he could and drop them, preferably into one of the fires. But while my group is a lot of fun, they aren't particularly tactically minded.

So my rules of thumb? I almost never have a single creature. It's almost never worked in any edition. Think of ways to make the environment interesting, and this can include the PCs taking advantage of it. For large number of monsters, use the mob rules. Don't be afraid to tweak the monsters a bit if you have more than 4 PCs. Try to figure out how to make sure every one feels like they can contribute. This is in part just getting to know the group, I want people to feel like they can make a difference, at least most of the time.

Last, but not least, even boss monsters should have an escape plan most of the time. That lets me cut fights a bit short if they're starting to drag and it's also just logical. Given the option most intelligent creatures will not fight to the death. Of course if the PCs can stop the BBEG from running away, let them!

*I do increase legendary action points a bit because it's a 6 person group, but that's about the only change.

 

[RangerWickett]

Late third edition, an Eberron campaign where the PCs were cops in Sharn.

During a sting operation against the monster mafia, the party laid a trap for some aquatic smugglers who are bringing it in illicit goods at the docks. It was night time, and the party had a flying taxi that they had posted outside of dark vision range, but the monster Mafia had harpy archers keeping watch, so the fight involved land, sea and air, with multiple range increments and illumination that moved around during the fight and vehicles that moved around and just a lot of things going on at once. Plus I think they were five player characters and maybe 15 NPCs total.

 

[Shiroiken]

I will say in general the most complicated combats involve a lot of types of creatures. Like an ensemble of 6 different monsters is much harder to run than 20 of the same type. This is doubly compounded with spellcasters. 1 spellcaster is always a pain, 2 spellcasters is more than double trying to keep straight who has what spell.

I will also note that creatures with reaction are like 2x-3x more complex than cretures without them, its so damn easy to forget about those reactions!

I've heard the complaint about casters before, and I have a pretty simply solution to it. It also helps with the variety issue as well. Anytime I know I'm going to have an at least halfway complicated fight, I set out the enemy battleplan as part of the description. Each creature type is going to have a general strategy, starting with primary targets and attack types. Casters should have at least 1 prep spell (if they get a chance before combat begins) and a descending order of spell preferences, based on the presumed layout at the start of combat. Obviously no plan lasts longer than the first punch, but having the plan gives me a reminder of what I should be looking at when a creature goes.

 

[Ralif Redhammer]

I will also do that with large groups...also whenever there's someone playing a monk that likes to blow all their ki points on spamming the flurry-of-blows and stunning strike combo, then always wants to take a short rest immediately after combat. I'm all for letting PCs do their things and be cool, but that one drives me up a wall.

*I do increase legendary action points a bit because it's a 6 person group, but that's about the only change.

 

[Oofta]

I will also do that with large groups...also whenever there's someone playing a monk that likes to blow all their ki points on spamming the flurry-of-blows and stunning strike combo, then always wants to take a short rest immediately after combat. I'm all for letting PCs do their things and be cool, but that one drives me up a wall.

Yeah, I just got done with a campaign where I was running a monk. Knowing that I could get a short rest after most fights made a huge difference. On the other hand, I got to 8th level and stunning strike only ever worked once or twice. I practically stood up and did a happy dance in our close-to-last encounter when it actually worked.

 

[Ralif Redhammer]

I've nothing against the monk class or stunning strike itself. It's when someone makes me roll four Constitution saves in a row, then wonders why they're out of juice.

Yeah, I just got done with a campaign where I was running a monk. Knowing that I could get a short rest after most fights made a huge difference. On the other hand, I got to 8th level and stunning strike only ever worked once or twice. I practically stood up and did a happy dance in our close-to-last encounter when it actually worked.

 

[DeviousQuail]

I've heard the complaint about casters before, and I have a pretty simply solution to it. It also helps with the variety issue as well. Anytime I know I'm going to have an at least halfway complicated fight, I set out the enemy battleplan as part of the description. Each creature type is going to have a general strategy, starting with primary targets and attack types. Casters should have at least 1 prep spell (if they get a chance before combat begins) and a descending order of spell preferences, based on the presumed layout at the start of combat. Obviously no plan lasts longer than the first punch, but having the plan gives me a reminder of what I should be looking at when a creature goes.

That sounds like a solid way of going about it. I like to do something similar with casters. I just give them each a theme. Lightning wizard, healer, pyro, summoner, etc. I don't really change their spell list but with a theme I can quickly pick a spell to match it 95% of the time. And if nothing jumps out at me I can always revert to a cantrip or magic missile.

 

[Fauchard1520]

My vote would be either the final battle of Rime of the Frostmaiden or a recent large-scale battle I ran that had multiple regions with different challenges, plus random battlefield events.

Was I their equal? I like to think so, but certainly with the former, which spanned three sessions, I had to take copious and detailed notes.

Not familiar. What were the fiddliest of the rules?

 

[Ralif Redhammer]

Behind spoilers, for those that haven't played or read it and think they might play it in the future.

Spoiler

In addition to her minions and the terrain, Auril has three forms, each with dramatically different abilities, legendary actions, and strategies, so it was kinda like having to plan three different boss fights.

Not familiar. What were the fiddliest of the rules?

 

[Quickleaf]

As you work your way through GMing a campaign, you add more and more complexity to your encounter design. Venomous critters appear. The orc shaman starts casting spells. Lair actions crop up when you finally meet that baby dragon at the end of the baby dungeon. It’s all cumulative, and it’s all meant to help prepare you for the actual end-boss of GMing: running high-level combat.

So here's my question to the board: What’s the most mechanically complex encounter you’ve run? Were you its equal, or did you find yourself overwhelmed by all the rules and options? Any way to combat getting bogged down in complexity?

(Comic for illustrative purposes.)

I ran an infiltration of a lizardfolk war camp that was pretty complex because it was (a) framed by a pseudo-skill challenge kind of thing I created wholecloth that doesn't technically exist in 5e RAW but I adapted the 5e rules for to make a better play experience, and (b) there were so many routes the PCs could choose and so many enemy types, that there was no real way to anticipate how it would pan out.

They ended up controlling a zombie dinosaur, assassinating a hag, and pursuing a fleeing lizard king in an aerial chase. Good times.