Silksong: Conquering the Pain, Anguish and Misery Quest in 2026

Even as the calendar turns to 2026, the sprawling kingdom of Pharloom continues to reveal its darkest secrets to dedicated explorers. Among the most talked-about hidden challenges this year is the side quest “Pain, Anguish and Misery” in Hollow Knight: Silksong. What initially appears as another errand on the Wish Board rapidly escalates into a breathtaking rematch against Trobbio — but this is no mere encore. The flamboyant showman returns as “Tormented Trobbio”, a boss so viciously enhanced that even veteran players find themselves scrambling. Despite being completely optional, this encounter has earned a reputation as one of the most thrilling and satisfying duels in the entire game, not least because it rewards the victorious with a unique hybrid Tool. If you’ve been wondering how to trigger the quest, what gear to bring, or how to survive the chaotic stage performance, this guide synthesises the latest strategies that players across the community have refined throughout 2026.
How to Start the Pain, Anguish and Misery Quest

Before the quest marker even appears, two important story gates must be unlocked. First, you need to have reached Act 3 of the main narrative — a phase that opens up after progressing far beyond the initial visit to the Deep Docks and resolving the tangled objectives of the “Silk and Soul” storyline. Second, the major quest “Return to Pharloom” must be completed, which involves your inaugural descent into The Abyss and the acquisition of the Silk Soar ability, essentially a super jump that reshapes traversal. Once these conditions are met and you are comfortably into Act 3 territory, make your way to Songclave
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