Dragon Encounters

Making dnd combat fun, finding monsters that fit together, monster tactics and strategies, and other ways of using the monsters of dungeons and dragons

BUGBEAR CHIEFTAIN: One-Round Challenges


Combat rating 4


1 Bugbear chieftain (CR 3)

2 Harpies (CR 1)


Combat rating 4


1 Bugbear chieftain (CR 3)

1 Owlbear (CR 3)


Combat rating 6


1 Bugbear chieftain (CR 3)

4 Bugbears (CR 1)

2 Saber-toothed tigers (CR 2)


Combat rating 7


1 Bugbear chieftain (CR 3)

2 Banshees (CR 4)


How to Use – Combat Encounters (difficulty 3)

The bugbear chieftain has a special feature that gives him immunity to most spell-inflicted conditions. This makes him a very good fit for a situation where he has an upper hand, and the players have only one round in order to avert disaster (examples below. Obviously.)

In many of these cases the situation is such that using spells loosely, area-of-effect spells in particular, might end up inflicting that disaster that the bugbear chieftain is planning to bring about. You can decide for yourself how sensitive you want the situation to be (how difficult you want to make things.)

The chieftain might be threatening to do it if the players don’t listen to him [probably to retreat, but use your imagination.] Or he might be planning to do it regardless and the players have only one turn to stop him. Even if he’s willing to bargain, you don’t want him to give the players too much time to listen or they’ll easily outmaneuver him.

A DM I know [and respect] often limits the time the players have [out-of-game] to decide what to do in tense situations like this. You’ll have to decide what works for you, of course, but it adds tension to the game in a good way, if you and your players don’t mind tension.

Even if the players fail to stop the bugbear chieftain, they might still be able to win the encounter. It will just be a bit more difficult.


  • The players are engaged in battle [or winning a battle] and suddenly they notice the bugbear chieftain. He’s high up next to the chandelier [possibly with the help of a rope they set up beforehand] and is threatening to bring it down, where the shattering glass will spray out and hurt everyone and/or set fire to the building.
  • They’re in the cellar and he’s got the lid to the coal chute. He’s threating to open it and bring down a flood of coal dust, blinding everybody. (It would be advantageous if his side has ranged fighters that can afterwards fill the room with arrows. It will be even better if there’s breakable items of the floor that will make a noise as the PCs walk, letting them know where to shoot. Without these, just say that the bugbears are good at fighting blindly (an advantage of practice at ambushes.)
  • He’s under the stairs and threatening to knock out the supports.
  • He’s threating to open the door or cage and unleash a nasty monster.
  • They’ve arranged a pile of dirt, rubble, and boulders on a hill and he’ll kick out the support and bring it down on the players. (Can also be done with a damn that he’ll destroy to release a river, but that’s a bit harder for them to arrange.)

A similar idea to these is that the exit from the base is narrow, forcing anybody going through to bend down, and he’s standing to the side of the entrance, with an action readied to clobber the first person to crawl through. [The bad positioning should give him advantage on his attack, as the PC can’t properly defend himself.]

Aside from the damage, the PC will be knocked to the floor, and if the area in front of the tunnel is narrow it will be hard for him to get out of the way and that will make other players unable to get through. (I’m envisioning a large boulder or similar five feet from the entrance, the bugbear chieftain on one side, and the third side can be clear, contain another boulder, a thornbush (difficult terrain and possibly damage, but possible to go through,) or for a very difficult fight, another enemy.)

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About Me

I have been a DM for several years, and I was designing home RPG games since my young childhood. I have been a fan of many different types of games (computer, board, RPG, and more) and have designed several for my own entertainment. This is my first attempt to produce game content for a wider audience.