LordEntrails
Hero
Sure. Thanks for asking nicelyI found the hardest thing to meet in OP's criteria were running challenging high level encounters that didn't take two or three hours to run.
Any tips there?

2-3 hour combat doesn't have to be bad. Not if it is interesting, dynamic and meaningful. I tend to think more along the lines of how to keep high level combat from being a slog or boring (i.e. just an exchange of resources). So here are my techniques for doing that.
As I said above, simplify NPC stat blocks. Having an NPC with 40 options is not time friendly. You are not going to use them. Get rid of them.
Know your creatures and plans. i.e. BBEG is going to do X if there are 3 or more targets in AoE. They will do Y if they are based. They will do Z when bloodied. Else they will do ...
Limit the number of NPCs. I don't mean this in terms of using more waves. Waves are tricky. They can be good and bad. But rather than 1 BBEG and a bunch of minions, use one BBEG (or a pair) and a set of supporting NPCs. Minions can be put in swarms if needed, or other minion rules can be used too (not going further down that road, whole another topic). But, if you have 4-6 key NPCs that you've chosen or made them strong enough, that can challenge any party.
Don't just do big bags of hit points. This is incredibly boring. imo, "Resist: all" is better than HPx2! but still uninteresting. One or two heal/regen traits are more interesting, and might even be interruptible (i.e. enabling player agency).
Train players to roll attack and damage at the same time. Train them to be ready to go on their turn (such as a house rule that if; when it is your turn you immediately declare your action and roll, you get a +1 to attacks/saves/checks).
Trust your players. To add the right modifiers. Missing a +2 or even a +5 or doing an extra sneak attack or anything else once in a while is not going to impact the enjoyment at the table unless you let it. To get their own movement right, who cares if they move 5ft too far? To track their own resources. Take what they say and run with it. Just like you expect them to take what you say and go with it. If you are not at a tab le with people you trust, and you are not all there to make a fun time for all, then running high level combats is not your problem.
Use digital tools.
"Garsh darnit! We're here to play D&D the way I did in 1978 and I don't want people playing on their phones or laptops, blah blah blah". Go ahead, be stubborn and shoot yourself in your own foot. But don't complain that your combats take too long. I'll just say it's your own fault. Because it is a choice you make and that makes it your fault. You can still have a car that you have to crank to start it, has no heat or air conditioning and you chose to drive it to work everyday. But I'm still going to say its your own fault.
- Ignore & recreate the encounter building guidelines
- Ignore & recreate monster statblocks
- Ignore & rebuild movement rules to account for a plethora of hazards traps & strongholds, hopefully just not ones that cause combat to drag on for hours
- Waves of monsters, just hopefully they manage to be challenging without dragging combat out for hours,
- Mix up the goals of the monsters you created to replace. Of course those monsters need to be quite a bit more beefy in order to survive long enough or hit hard enough for goals other than fight to the death to happen & hopefully it can be done wiythout taking hours or shifting the solution about challenging combat to something that is not combat.
- Interrupt the rests players try to take. The question was about "challenging combat encounters for high level characters that don't take two to three hours to run" and this particular perpetual motion machine goes nowhere but "ok now that we finished that interruption, lets take a rest...
as we will if interrupted a second third or ourtysecond time
"
You really don't seem to be trying to actually engage in useful discussion. Show me I'm wrong and I will engage.The third of these doesn't even sound like it's about combat & the second one might as well admit that everything suggested should be ignored because the GM will need to redo everything from square one again based on PC builds.
Sure I have. I've had them take longer than 2 hours and be a bore, and be a great time that I wish could have gone on for 10 hours. Time is a poor metric for measuring fun. You are going to be playing for # hours, if all that time is fun and everyone is feeling like their characters are meaningful and growing, who cares if you accomplish 1 encounter or 5?I've read wildly different things regarding folks' experience of time spent in combat on these forums- but you've never had a level 15+ combat that took 2+ hours in 5e?