
Upon progressing to Act 3 in Hollow Knight: Silksong, you may feel you’re nearing the conclusion of the game’s offerings. However, it won’t take long before you discover that numerous mysteries and side quests still await you, keeping the adventure alive and vibrant.
One such intriguing side quest is titled “Pain, Anguish and Misery, ” which thrusts you into battle against a familiar foe. This time, however, you’ll encounter a “tormented”version of the boss, considerably more powerful and aggressive.
Tackling this fight is entirely optional, yet bypassing this quest means missing out on one of the most exhilarating encounters in the game. Not only does this battle reference the iconic anime *One Piece*, but it also rewards your efforts with an impressive new Tool.
To ensure you don’t overlook this quest, we’ve crafted a comprehensive guide detailing how to trigger it, prepare effectively, and employ the most effective strategy to secure victory. With our step-by-step instructions, you can banish any “pain, anguish, and misery” from your mission.
Initiating the Pain, Anguish, and Misery Quest in Hollow Knight: Silksong

To activate this quest, you need to fulfill two essential prerequisites: First, unlock Act 3 of the main storyline, and second, complete the quest “Return to Pharloom, ”where you will explore The Abyss for the first time.
Reaching Act 3 involves several specific tasks, such as locating all Lost Fleas and finishing the “Silk and Soul” quest. Continue following the main narrative, which will guide you to the Forge Daughter in the Deep Docks, ultimately enabling the Silk Soar ability—a powerful “super jump.”
Once you’ve delved deeper into Act 3, navigate to Songclave, a quaint village in the eastern area of the Choral Chambers. Here, interact with the Wish Board to activate the “Pain, Anguish, and Misery” quest.
Reading the quest’s description provides a clue that Trobbio is gearing up for another performance, prompting you to re-visit his stage located at the Citadel’s Stage in the Whispering Vaults, right above a bench equipped with a Bellway and a Ventrica.
Optimal Readiness for the Tormented Trobbio Boss Encounter

Expect an extravagant showdown, as Trobbio—the ultimate showman—will showcase an enhanced version of his Act 2 moveset, exhibiting increased speed and complexity.
At this point, you should have most passive abilities unlocked, including the crucial Silk Soar. Additional must-have abilities include Swift Step (the dash, acquired in the Deep Docks), Faydown Cloak (the double jump, found in Mount Fay), and Drifter’s Cloak (enabling gliding, unlocked in Far Fields).These skills will greatly aid your evasion tactics against Trobbio’s assaults.
Your build is crucial; consider the Reaper Crest for boss fights, as it permits you to wield two Tools of each color—enhancing Hornet significantly with dual Red, Yellow, and Blue Tools.
For your Tool selection, opt for a balanced mix to ensure both protection and offense. Recommended Tools include Tacks (from the “Roach Guts” quest), Cogfly (craftable in the High Halls’ workbench), and Pollip Pouch (from the “Rite of the Pollip” quest).This combination enables continuous offensive maneuvers and poison damage from the onset of the battle.
For your remaining slots, equip Hornet with more durable defenses using Magnetite Dice (acquired from Lumble the Lucky in Blasted Steps by winning the Dice mini-game or by waiting for her demise) and Fractured Mask (obtained from the Mottled Skarr merchant in Hunter’s March).This duo provides an extra health mask and a 10.1% chance to block incoming attacks automatically, enhancing your survivability.
Strategies to Defeat the Tormented Trobbio in Hollow Knight: Silksong
When the battle commences, charge towards Tormented Trobbio and strike him; this maneuver delivers bonus damage. Then, center yourself in the arena and prepare for his next offensive.
Trobbio has five distinct attacks that can potentially create chaos if not monitored closely. Here’s a breakdown:
- First Attack: Trobbio leaps and releases three (or more) poisonous balls, generating damaging smoke. Either strike the balls to neutralize them before they cause damage, or simply dash away from them.
- Second Attack: He might effortlessly toss three poisonous balls even before appearing on stage. Again, hitting the balls or dodging is your best defense.
- Third Attack: Trobbio becomes a tornado moving towards you while summoning additional tornadoes on both sides. This is your prime opportunity to counterattack. Jump on him and start dealing damage, continuing until he unleashes the side tornadoes.
- Fourth Attack: He creates multiple fireworks in a circular pattern above, damaging everything beneath. Evade this by dashing, double-jumping, or gliding away from the illuminated circles—focus on defense rather than retaliation.
- Fifth Attack: Similar to the fourth, he generates shiny spotlights that explode into quick diagonal fireworks. Dash away to remain safe from harm.
Throughout his onslaught, Trobbio will frequently reposition himself below the stage. Track his movements via the jumping tiles to anticipate where he’ll surface next. This becomes a pivotal aspect of counterattacking effectively—strike as he emerges, then swiftly dash back to maintain your distance.
Pay attention to the rhythm of his attacks, as he intensifies the frequency and complexity as the fight progresses. His poisonous balls can double, so eliminate them promptly to maintain a safe battlefield.
Utilize your Cogflies and Tacks strategically to hasten your victory as you edge closer to defeating him.
Rewards Upon Vanquishing the Tormented Trobbio

Upon your triumph over Tormented Trobbio (be sure to savor his exit from the stage—it’s a spectacle), you will receive an immediate reward: the Dark Mirror.
This special Blue Tool fuses automatically with the Claw Mirror (earned from your initial fight against Trobbio in Act 2) to create the Claw Mirrors—a hybrid Blue Tool! This remarkable device unleashes a scorching blast, damaging adversaries during its binding. Don’t forget to equip it via your Tools menu—it’s a fantastic addition to your arsenal!
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