The Pit of 100 Trials is the hardest challenge in Paper Mario: The Thousand Year Door. There are 100 floors of enemy battles that get progressively more difficult. There are no save or heal blocks in the pit. Every 10 floors you will find a reward chest instead of an enemy battle.
The Pit of 100 Trials can be found in Rogueport Sewers and attempted any time after you find it. The longer you wait to attempt it the easier it will become, but the less useful the rewards will be. Here are some general tips for taking on this challenge:

The first 10 floors of the pit are filled with very easy enemies like Goomba, Spania, and Fuzzies. Some have unique varients, so make sure you Tattle right away if you want to complete your log. The reward for reaching Level 10 is the Sleepy Stomp badge.

The enemies on these floors are a little stronger and more varied, but still shouldn't give you much trouble in the late game. These are enemies like Piders, Dark Puffs, and Clefts. The reward for reaching Level 20 is the Fire Drive badge.

The enemies get a little stronger on these floors, with the likes of Spiky Gloomba, Boos, and Bandits. The reward for reaching Level 30 is the Zap Tap badge.

Dark Koopas and other enemies that have higher defense make there debut on these floors. Remember that many of these enemies can be flipped over and exposed with attacks like Bobbery's Bomb. Pink Fuzzies that can drain you of your much needed FP also make an appearance, so take them out as quickly as possible. The reward for reaching Level 40 is the Pity Flower badge.

The basic enemies on these floors often get wings and spikes added to them. Spiky Parabuzzies can be a pain to deal with unless you have the Spike Shield badge equipped. You'll also find enemies like the Bulky Bob-omb and Lava Bubble. The reward for reaching Level 50 is the Strange Sack, which allows you to carry up to 20 items.

Things start to pick up past the half way point. You'll run into new enemies like the Badge Bandit, which can steal a badge from you in battle. You can get it back, but you'll need to re-equip it. You'll also find Ice Puffs, Dark Boos, and Red Chomps. Koops's Shell Slam can defeat a whole row of Red Chomps (Level 59) since it ignores defense. The reward for reaching Level 60 is the Double Dip badge.

Things really get kicked up a notch with enemies like Dark Lakitu, Dark Craw, and Frost Piranha. Later on you'll run into some brand new enemies like Wizzerds and Dark Wizzerds. The enemies here start to reward some serious star points, so watch when you are about to level up as you'll get a full heal and FP refill. The reward for reaching Level 70 is the Double Dip P badge.

You'll start to see some enemies with high Defense and HP like the Dark Koopatrol. Make sure to knock these guys on their back when you have the chance. Koops's Shell Slam works great on these guys as well. You'll also see Phantom Ember, Swoopula, and Chain Chomp. You'll want something like the Piercing Blow badge or Koops's Shell Slam to deal with the 5 defense of Chain Chomps. The reward for reaching Level 80 is the Bump Attack badge.

Even more strong enemies are introduced on this level. Dark Bristle, Dark Arantula, and Piranha Plants. These enemies have very high Attack, Defense, or both. You'll want to keep using moves that ignore enemy defense to take them out. The reward for reaching Level 90 is the Lucky Day badge.

You'll start to encounter the toughest enemies in the game, including several new variants at these levels. These include Elite Wizzerds (8 Attack, 5 Defense), Poison Puff, and Bob-ulk. It can be difficult to keep Goombella alive long enough to get a Tattle on the new enemies. Luckily you should level up a couple times on these floors, granting a full heal and FP refill in the process.

Level 94 features a row of five 20 HP Swampires that will suck the health out of you with every attack. The secret to that battle is Flurrie's Gale Force, which will blow most of them away for minimal FP. The same strategy can be applied on Level 95 which features 5 Dark Wizzerds. One Gale Force can finish the battle and net you 50 star points.

On some of these levels you may also encounter an Amazy Dayzee. Make sure to target it first so that you can get a ton of star points before it runs away or uses it's 20 Attack power on you. The rest of the battles on these levels can also easily be dealt with with Gale Force.

When you reach the final level of the Pit of 100 Trials, you will be met with thge hardest boss in the game: Bonetail. She's the older sister of Hooktail and features 200 HP, 8 Attack, and 2 Defense.

A good strategy is to have Flurrie lead as she is a tank who can deal consistent damage. She can also regularly heal herself with Lip Lock. You can then have Mario use the Power Lift special move to give your team a consistent Attack and Defense boost for the fight. Piercing Blow is a good move to use as Mario as it ignores Defense with a low FP cost.

When Bonetail's health starts to get below half, she will begin healing herself 20 HP at a time. This will happen every few turns, so you'll need to be able to outpace this regeneration to keep up. If you have the right badge combination (especially a 5 HP build), this should be no problem. If you've focused all your efforts on HP and FP, it might be tough to keep up.

Eventually Bonetail will be defeated and you will be rewarded with 999 coins and a single star point. More importantly, you'll get the Return Postage badge, which deals back half the damage done to Mario. Congrats on beating the hardest challenge in the game!
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