Before I get into the subject material, the purpose of this post is to give people a resource of tips to make high-level encounters challenging while remaining fun & interesting. Questions are fine but please try to keep responses in this vein.
Tip 1: Know thy enemy
And by "enemy" here, I mean your player's characters (PCs). They are the enemy of your monsters. Know what they are capable of, what level of damage they can output, what tricks they can pull, how many counterspells they have access to. The goal isn't to negate these things entirely, just enough to make them think rather than repeating the tactics that have got them through many previous battles.
Tip 2: Run the numbers
For a big bad boss battle, you want it to run the course. You want to make sure there is real jeopardy for your PCs. This means, among other things, making sure your monsters have enough HP to last long enough and enough damage to create some tense moments. Make some crude napkin-math calculations.
Total party HP x 2 / number of rounds = average damage per round for all monsters.
Reminder, this is meant to be crude, you can't math your way to fun encounter design but a little can help. Why x2? Because your party will have abilities you'd forgotten about, healing spells, consumables, magic items etc. If you are running multiple monsters on the board (you probably should), as monsters die, there also goes their damage potential.
Do similar for PCs damage output for total HP of your monsters but don't multiply by 2.
Tip 3: Break some eggs
And by eggs, I mean rules. Legendary Resistances are an example of "breaking rules" in the way I'm meaning. A twin boss with shared HP, a spellcaster with a shield providing them with invulnerability fed by a crystal that needs to be shattered, a spell the players don't have access to. Monsters can and should break these rules.
Tip 4: Wear them down
Don't let your party off light, give them some encounters earlier in the day, make them expend some resources so they don't come into the final fight at 100%, ready to nova.
Tip 5: Don't pull your punches
At high-level play, your characters should have the tools and resources to recover from many setbacks including death. Don't be afraid to set them back a little, especially if they went into it with eyes open.
Tip 6: Change the win condition
This is one you'll hear a lot and with good reason. At high level play, sometimes the best way to challenge the PCs isn't to challenge them directly but to target a place or people who are dear to them. The point is to change the question from can we win? to can we avoid losing x? Is the enemy a massive rampaging beast with thousands of hp, headed unerringly towards the city? Perhaps an insane druid who has turned all of the beasts of the land into his unwitting pawns? Maybe he gets stronger with every beast under his command that is killed. Give the PCs something other than their own hides to think about. The Barbarian may have 200HP and be a walking destroyer of worlds but that commoner has 4hp.
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More about Dungeons & Dragons OnlinePost: "Making Challenging combat encounters for High-level PCs" specifically for the game Dungeons & Dragons Online. Other useful information about this game:
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