D&D 5E Silly Dhampir tricks (prone on ceiling)

[Bill Zebub]

Think about this, do you want "challenges" that are just scenes for your party to have guaranteed victory at no cost or risk? You can play this way and be guaranteed participation ribbons all campaign long.

I love fights where you feel like you're on the verge of a TPK the whole time. And I want DMs to both create encounters and run the monsters to make them challenging. But it's annoying when the challenge comes via questionable rulings.

For the scenario in question, I would have ruled that the fiend still gets two attacks because jumping is movement, but with disadvantage for the irregularity of the attack, cancelled by advantage for the prone target. And had the player announced their plan before executing it, I would have told them ahead of time how the ruling would go. (Which is an example of why it's a good idea for players to explain their reasoning before trying to be too clever with their action declarations.)

P.S. "participation ribbons" isn't a very respectful way to make your point. Just sayin'.

 

[Shiroiken]

First of all I don't think you go prone on the ceiling, but don't know RAW (RAI seems like no, but RAF says yes). I wouldn't allow it myself.

As for tactics, it really depends on the intelligence of the enemy. A fiend is going to have good tactics and going after the cleric is a no brainer. A bunch of beasts taking attacks of opportunity to get around the front line doesn't seem right (although going wide around them to easier meat does). Terrain and setup make a big difference as well, since a confined space generally favors the PCs (who can prevent enemies from getting behind them without major effort). As a player, I take my enemy's potential tactics into consideration, and in open areas often spread out to avoid what we call "fireball formation."