Multi-Skill puzzle: The Deeproot Dragon

Looking for some fine tuning on this one!

for context, I’m planning this as part of a one-shot at a place that does those weekly. The pace is relaxed so the session tends to be a bit sparse to get through it all on time. I’m planning on three encounters: combat, puzzle, boss fight. The shtick is they’ve been trapped by a mad wizard who is running them through tests for “data.”

for the puzzle, I basically want to have a skill check with some creativity mixed in. A hazard players need to cross that can be solved with a wide variety of skills. DC is the same no matter which skill you’re using, but you have to tell me, the DM, how your skill can get you through this. A small amount of damage per failure keeps some stakes, and a single check (per player) to get by keeps things moving quickly.

on the back end, I want the hazard to be such that a wide variety of skills can plausibly be used to get around, and it doesn’t push you towards one particular skill. But each check also needs to put you in the path of danger, so they risk taking the fail damage.

Here’s what I have: In a wide hall, the wizard has chained to the ground a huge elemental plant dragon. The floor, walls, and high ceiling are all overgrown with roots and foliage. A chain on its neck leads to a hole in the floor, and out through another hole to a mechanism in the wall to the player’s right. An antimagic field fills the chamber, so no spells! The dragon is unfriendly but willing to engage in conversation. Any player who enters his reach (necessary to pass the wide hall) gets snapped up by the dragon, who deals about as much damage as a “setback” trap before tossing them back.

Players could try to pull the chain tight and secure it to reduce his reach (Athletics), figure out the mechanism controlling the chain (Investigation), Try to sneak through the foliage on the floor (Stealth) or climb the roots on the ceiling to go over its reach (Acrobatics). They can also try to either deceive or persuade the dragon into letting them through. the Wisdom skills don’t seem to apply as much here: to be fair, I’d like there to be a way for perception and/or insight to get through somehow. Maybe perception for some trying to spot a way around the dragon, and success will notice a tunnel opening in the floor.

the other challenge is that every check needs to involve risk of “fail damage”. Some checks, if failed, involve the player still standing out of the dragon’s reach (such as failing to deceive the dragon). Considering rolling wisdom and charisma skills privately (ask for their bonus) and telling the player regardless of roll that they think they found a solution (aka the dragon acts like he’s been persuaded or there appears to be a hole in the floor just inside his reach). Then they have to try crossing to see if they actually succeeded.

anywho, let me know what you guys think!