My players are either very good or I am a lame OL. Either way, I ordered Well of Darkness because it is supposed to balance the game more towards the OL but is has not arrived yet. I have a game scheduled with friends tomorrow night. I will have five heroes total.

What is the most brutal, meatgrinder-like quest in the original game? Or is there a downloadable quest that is even harder? I really want to press my group. Not only do they run a rapetrain on my monsters, they love talking smack to me about it.

Help me bring the pain.

Quest 7: The Black Blade.

Without question.

Every other quest in vanilla JitD is ultimately balanced in the Heroes' favor (though some more than others).

This one is definitely balanced in the OL's favor.

Doesn't mean they can't win, but it is the hardest map by FAR.

There's a thread on boardgamegeek with difficulty ratings and comments for all the JitD quests. It puts quest 7 as being the hardest by a substantial margin.

It's no great surprise that the heroes are slaughtering you if you've got 5 heroes in the game, though. The number of heroes in the game can dramatically swing the difficulty, and that's more than the game is even theoretically designed to support (the "5" on the monster cards means 5 players including the overlord--only 4 actual heroes). If you've got 6 players that all want to play, I guess you may be stuck, but if you have the opportunity to play with fewer, I definitely recommend trying that. And with 5 heroes, I'd definitely negotiate some sort of extra advantage for the OL--the normal scaling pattern would be for monsters to get +1 health (compared to the 4-hero stats) and for the OL to collect 5 threat per turn, but since those scaling algorithms clearly don't scale enough in going from 2 to 4 heroes, giving the OL some additional advantage on top of that wouldn't be at all unreasonable. Maybe start with one or two power cards in play or something.

Awesome, I wanted to run Black Blade, it looked fun. We assumed 5 heroes was the max, I guess 2-5 players would include the OL. Thanks for the responses.

Err, yeah, that's actually my guide too. I guess I probably should've linked it myself. Good thing others are paying attention.