Party recently left Wyllow's forest, and they're in "The Lost Levels" or whatever it's called. It has the temple and library devoted to Dumathoin.

My DM style is usually to flaunt their mortality but be very generous with magic items. It's a weird mix of "one or more of you *will* die" and "surprise, here's something super cool".

Anyway... I wrote myself into a corner by putting the horse before the carriage. They've all been contacted individually by an unknown entity who has challenged them to Mortal Kombat. The catch is that whoever accepted the challenge was allowed to pick any rare magic item they want. They will get the item for the challenge and the item can't confer AC, and it can't be a weapon (they each already have a 1 version of starting weapons). What I find fun about it is the freedom of choice, and potential for great reward at a huge risk.

What I don't have figured out is the challenge. I don't want to spend a whole session doing X number of separate challenges and splitting the whole party up. That said, I do want the challenges to be individual. The main point of this risky reward is to illicit hubris, and then slap them with the chaos of Undermountain...

The last important bit, which is where punishment of hubris comes in to play, is that even if they decline the challenge, they will still be rewarded by Halaster with their own personal rare magic item.

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1. Illicit hubris by getting individuals to accept a challenge from a totally unknown entity with guarantee of great reward (though you might die shortly after getting it if you fail the challenge).
2. Sow doubt in anyone who declines on whether they made the right choice.
3. ​
4. Profit

What do y'all think? Keep in mind me and my PCs have no problem with a character death, but I'm not trying to actively kill them. I guess you could say I'm here to provide them the opportunity to kill themselves, as any good DM does.