When:This challenge also takes place at the beginning of the game.
Where:It takes place in two places. First, in the Village Dungeon (SE of Terinyo), then in the Infinite Caverns. It must be noted that you must enter Terinyo and talk to the village elder for this challenge, or the Village Dungeon will not appear.
What:This challenge is an easier version of the Ironman Challenge, for those who find it too discouraging. The first difference is that you must start with a random PC, no prefabs. After you are dropped in the mountains, chat with the Village Elder. Then leave Terinyo and go to the Village Dungeon. After defeating Yriggs, go back up into the wilderness and go to the Infinite Dungeon. From this point on proceed as you would with the Ironman Challenge. The advantage this gives you is giving you ~6 levels when you start Ironmanning.
How:Since this challenge lands you with a random PC, you don't really have much choice as to how he plays. The only strategy I can think of for this is to spend lots of time in the Village Dungeon until it becomes unfeasable for gaining experience and weapon skills. For instance, with a dwarf about level 8 and a troll about level 4.
1.Drop everything and do it unclothed.
2.Never use any other equipment except what you start with.
3.Use all melee weapons as missles and all missles as melee weapons.