Dealing with PCs that can fly at will

Plan your encounters accordingly. A lot of monsters from the books have zero chance against a flying party. Without flying, good ranged attacks, good evasion abilities, or an enviroment that favors them especially, your monsters will not stand a chance.

Sometimes that is okay, but if it happens a lot, it gets boring. Fortunately, most players will get bored after they wipe the floor with yet another group of hapless ground-pounders and will limit their flying 'just for the fun of the fight'.

I find that if there is a huge difference in mobility between the PCs and the opponents, and their is no way to compensate, combat gets boring. Last session one of our opponents was a small CR 17 fighter-type dude in full plate armor. He no good ranged attacks, a 15 ft. move and the encounter took place in a huge chamber. We (a party of 15th lvls) hardly paid him any attention, while he was constantly attempting to engage. The flying, haste spells, monk movement was just too much for him. Too add insult to injury, the wizard hit him with an empowered ray of enfeeblement on a flyby, causing him to lose so much strength he had to drop his weapon and shield, and was practically pinned in one place. We even used him as cover against attacks from other opponents. Oh, I almost forgot, he was supposed to be the BBEG.

When I look at new monsters, I always look at their capabilities vs. flying opponents. If they have none, they usually shouldn't be much more than CR 14-15 or so. I really laughed at the Fiendwurm in the MM2, supposedly CR 28, but it cannot do much about flying opponents. A standard party of 16th lvl characters should be able to beat him every single time because of Flight.

At higher levels it gets easier and more seductive for the party to practice hit'n'run tactics (using flying, ranged attacks, teleportation etc.). If you want to make an opponent that cannot counter such measures directly more challenging, consider creating extra consequences. Maybe the opponent is holding others hostage, maybe their is a time limit, forcing the PCs too take more risks, etc. etc.
 

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I think it's fairly obvious what to do.

Don't have purely ground-based challenges if the entire party can fly.

Erm. That's about it.

By the time they can fly, the party has dealt with a large number of falling-death scenarios. They're just not interesting anymore. Pit traps, large chasms and the like are not suitable challenges. In fact, from a player point of view, they're dead boring.

Maybe the very FIRST time they encountered them, they were interesting. But a climb check (and probably some use rope checks) later, the obstacle is overcome, and a more-or-less foolproof plan for overcoming it in future is in place. If anyone around you is a computer professional, I don't doubt that you'll start hearing "we use the cliff scaling macro" or "chasm crossing macro" instead of them detailing out the whole thing.

Actually, at that stage you should just be saying "you come across a chasm, are you crossing it? Yes? Fine, done."

Most monsters with no ranged attack and no flight capability are very low CR for their abilities. There is a reason for this. They are crap. Stop using them unless you're using them in tandem with a flying creature or ranged attacker.

Against a ground-based target with the ability to hit flying creatures, flying is a negative, not a positive. Lack of cover can be punishing.

And of course, in a dungeon, you'll often find that creatures can reach a flyer anyway.

Similarly - don't try to challenge high level players with:
starvation
thirst
encumberance
most environmental effects
invisible creatures
other forms of lack of resources
navigation (ie - getting lost in the woods)
foes with a landspeed of less than 40' and no ranged abilities
undead of less than 5 equivalent hit dice
etc
etc

Progression in D&D has a lot to do with keeping the game interesting. None of these are interesting after the first time they've happened. In fact most "lack of resources" scenarios were never interesting in the first place. Consequently, at higher levels there are a whole raft of spells devoted to doing away with boring adventure concepts. If you find the PC's are going to make short work of something, it's a good clue that you should never have used it in the first place, and that you certainly shouldn't go out of your way to negate their advantages just to make it stick unless it's somehow appropriate.
 

Not all flight is magical. Deal with flying patterns, turning circles, hovering and such. Flight is only a bother at Perfect maneuverability. Aside from that movements a real tedium, turning changes, minimum speed in flight.
Of course the best way to deal with them is WEB, and such. maybe Wall of Stone/Iron over the top of them.
Flight is merely a net throw from being falling.
 

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