How to Beef Up Your D&D Boss Fights

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In just a few weeks, my regular weekly D&D group will be finishing up “Curse of Strahd,” the latest hardcover adventure for 5th Edition. This means my party of scrappy murder hobos will be marching into Castle Ravenloft to finally have it out with the dark master of Barovia, Lord Strahd. He’s a vampire in case you don’t know the story. He’s basically D&D Dracula. “D&Dracula” if you want to be cute.

Here’s the problem. Strahd may have been the stuff of nightmares when my party first entered his domain, but now they have spent months grinding, leveling, and collecting any magic items that weren’t tied down (and maybe even a few that were). Looking at the math, I have to consider the fact that my party might just nuke Strahd in round one. That would be, in a word, unsatisfying. If this were a homebrew campaign, I’d simply rework Strahd into a new, more powerful form, but I’m trying to stick close to the monster as presented in the book. I have some work to do.

Remember, we’ve been building up to this for months. If the fight is a walk-over, nobody will be happy. I’m not looking to TPK my party, but the big bad has to feel big and bad. So let’s explore some of the tricks I’m going to use to boss up my boss fight and maybe you’ll find some useful tips for your own games…


Any party is most dangerous just after they’ve completed a long rest. They have all their hit points and all their spells. They also have a wild gleam in their eyes and the promise of a new day’s loot. This is not the party I want to encounter Strahd. In fact, I want Strahd to vampire-float up to them exactly after they cast that spell they’d been saving to use against him. Thankfully the 200-ish rooms of Castle Ravenloft are already designed to do exactly this, exhaust as much of the party’s resources as possible before they hear the fateful “Good Evening…” of Strahd’s approach.

Here’s a little mechanical help for DM’s who have trouble keeping their party from constantly resting and refreshing their abilities. Remember, according to the rules, a party can only take a long rest for 8 out of any 24 hours.


I’m not a huge fan of 5th Edition’s surprise rules. Either the party gets a free round to pound down your monsters before they act or you do the same to the party, which feels cheap. In addition,  most parties simply can’t be surprised because someone has the “Alert” feat or an item that does the same. If you want your big bad to seem dangerous, they have to control the pace at the start of the fight. To that end, my plan is to have Strahd enter an already existing combat. Imagine the look on their faces when, in the 3rd round of a fight with some of Strahd’s animated armor, in trots the vampire lord himself. The fight gets bigger and they have nothing to do but react and change plans mid fight.

As a pretty devious player myself, I know how hard I can be on DMs if I know a big fight is in the next room. My fellow party members and I will plan our attack with black ops like precision. Strahd is too smart to let that happen, so I won’t let it happen either.


If I had one bad thing to say about 5e, it would be how poorly it deals with numerical advantage.  I guess it makes some sense that a horde of goblins should be a threat to even a badass 5th level fighter. However you want fights to feel cinematic, Dracula er… Strahd should be able to fight off 7 heroes by himself. Sadly the math doesn’t really work that way. So Strahd is going to have to bring friends to split the party’s focus, but also because that’s how smart monsters fight.

I already plan on Strahd entering into the tail end of another combat, so we’ll have a few straggling monsters from that, but I also think some Vampire Spawn or Bat Swarms should make an appearance in the first few rounds. This won’t stop the party for focusing on Strahd, but when they start counting hit points they’ll want to take out the smaller monsters quick if they can. After all, dying by bat swarm is still dying and they should feel like they need everyone they can against the master of Barovia.


Putting your final battle in a big empty room is a good excuse for your party to overwhelm your boss monster with underwhelming emotional results. Strahd is actually designed to make use of a creative environment with his suite of legendary and lair actions. Therefore, my intent is to stage the big fight in a room that gives Strahd (and me) something to play with. Castle Ravenloft offers a variety of trap rooms, staircases, balconies, pools of standing water.  I wonder how the party feels about a 100 foot drop? Vampires have the “spider climb” ability, I should point out.


I never walk into a fight with the intent of killing one or more of the party members. That said, it’s not going to be much fun if Strahd or his minions pull punches or avoid the killing blow. As the DM, my job is to fight like the brilliant master vampire would fight… and that means not leaving a player alive with 5 hit points to later heal and stab him in the back. Even at my best I can’t expect to hold the party down so badly they can’t save their dying comrades when it’s all over. In every on-screen fight with Dracula I can remember, he tosses aside a few attackers right off the top then goes mano-a-mano with Van Helsing. This should feel like that. Strahd is going to focus his fire, hit hard, and move on. If the party’s healer is efficient, most players won’t stay down long, but they can’t and shouldn’t expect a vampire lord to give them a moment to breath in a fight their whole lives have been building up to. Ok, maybe I’ll kill one. That’s the risk you take being a hero, right?

Of course, if you’ve read “Curse of Strahd” you know there is a lot more that goes into the fight in terms of fortunes and allies and everything else. As a Dungeon Master, it’s going to be one of my hardest crafted scenes and hopefully the players like it. I hope you can use these techniques in your own games as well. Be it vampires or dragons or the Tarrasque, make it big and bad, something worth singing victory songs about.

Thanks to Matt Olsen for donating the cover image fro this article, Matt is an Illustrator/Designer that lives in Parker, Colorado. Also, he’s a secret robot. Don’t tell anyone. Check out his stuff on his  DeviantArt.

Tell us about your best D&D boss battle in the comments. Do you have advice to how to fairly amp up Strahd? Leave that in the comments too. 

Header Image Credit: Matt Olson
Internal Images Credit: Wizards of the Coast 

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