I have a confession: I am not good at Hollow Knight: Silksong. I am stubborn, though. I have spent dozens of hours getting humbled by its platforming, its map, and its bosses. And as of 2026, after several post-launch patches, the hardest fights still feel like they were designed by someone who wanted to see me cry. Here are the ten bosses and boss-like encounters that broke me the most.
| Rank | Fight | Why it hurts |
|---|---|---|
| 10 | Last Judge | Act 1 skill check with fire and a brutal runback |
| 9 | Groal the Great | Waterborne poison frog with pendulum problems |
| 8 | Savage Beastfly (second) | Optional, add-heavy, attention-splitting |
| 7 | Widow | Fast silk traps and unpredictable bells |
| 6 | Phantom | Lace but meaner, faster, and less fair |
| 5 | The First Sinner | Needle hell and exploding AoEs |
| 4 | High Halls Arena | Eleven waves of pure endurance |
| 3 | Moorwing | Flying orb patterns from a bad dream |
| 2 | Sister Splinter (pre-patch) | Two-mask claws and Shellwood lockdown |
| 1 | Skarrgard | Early-game wall with a lesson |
10. Last Judge Is a Mid-Game Skill Check
The Last Judge is not the hardest boss in a vacuum, but she is the hardest boss when you are still learning. She is the final boss of Act 1, and she exists to make sure you have actually learned Silksong’s mechanics. Her attacks are diverse. Phase 2 sets the arena on fire, literally engulfing you in flames. When you finally win, her weapon explodes and gets one last hit in. And the runback is miserable; I lost my cocoon more than once before I even reached her. Fighting her is like trying to fold a fitted sheet during a house fire.
9. Groal the Great Is Too Big to Dodge
Groal is a waterborne frog boss in Bilewater, and he ruins an area that already ruined my day. You have limited time to hit him when he pokes his head above the water. He uses poison projectiles and a foul breath attack that pulls you inward. He bullies you into corners with his bloated body, summons adds, and his arena has swinging pendulums and poison pools. It is a geometry problem where all the angles are poisonous.
8. Savage Beastfly’s Second Appearance Is Shockingly Hard
The first Savage Beastfly fight in Far Fields is relatively easy. The second one, in the already frustrating Hunter’s March, is an optional boss at the Chapel of the Beast. You do not have to fight it again, but if you do, you are in for a challenge. Phase 1 uses floating slam attacks that leave it vulnerable. Phase 2 summons a number of annoying adds that exist only to distract you, splitting your attention between multiple moving targets until you lose track of the real threat. I lost that thread more than once.
7. Widow Has Quickly Become an Icon
Widow has become one of Silksong’s beloved bosses for her unique design, silk-based moveset, and difficulty. You face her about halfway through Bellhart. Like Hornet, she summons silk to ensnare you and occasionally drops large metal bells on your head. The issue is phase 2, when her bell drops become less predictable and her base attacks get faster and harder to dodge. She is quick and unpredictable, and you need to heal, but you also need silk and space. That tension is the whole fight.
6. Phantom Makes Bilewater Even Worse
If you thought your first bout with Lace was difficult, wait until you fight Phantom. The two bosses share a lot: they can parry your attacks, dash across the battlefield, and perform devastating AoEs. But Phantom is tougher. They are faster and significantly less predictable. You are always too late to dodge their projectile throws, just a little too close to jump over their dash attacks. Phantom covers the entire battlefield, leaving you no safe space to cower until it
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