You finally made it. After trekking through the claustrophobic, fungal mess of the Fungal Wastes, you use the City Crest and the gates of Hallownest’s capital creak open. The music shifts. The rain starts. It is beautiful, honestly. But the City of Tears bosses are a massive reality check for players who think they’ve mastered the game after beating Hornet.
The difficulty spike here is real.
The City of Tears serves as the emotional and mechanical heart of Hollow Knight. It’s where the lore gets heavy and the combat gets frantic. You aren't just fighting mindless bugs anymore; you are fighting the elite leftovers of a fallen empire. Some of these encounters, like the Soul Master, are legendary for making new players quit. Others, like the Watcher Knights, are basically a gatekeeper for the ending of the game. If you are struggling, don't worry. Everyone does.
The Soul Master and the Vertical Nightmare
Most people find their way to the Soul Sanctum first. It’s a terrible place. It’s full of Soul Twisters that teleport and fire homing orbs at your face. By the time you reach the Soul Master at the top of the spire, you’re probably already low on health and stressed out.
The Soul Master is a lesson in patience. He teleports constantly. One second he’s across the arena, the next he’s slamming into the ground to create shockwaves. You have to learn the rhythm of his dives. If you jump too early, he’ll fake you out with a mid-air dash and crush you anyway. It’s mean.
The most important tip? Stay in the middle. If you chase him to the corners, you’re going to get trapped by his rotating soul orbs. When he does the "clock" move where the four orbs circle him, stay grounded in the center. As they move back across the screen, hop over one. That’s your best window to heal or get a hit in.
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And then there’s the fake-out. You "kill" him, the music stops, and you go to pick up your reward. Then the floor breaks. Phase two is pure chaos. He stops the fancy spells and just starts slamming the ground repeatedly. Don't try to be fancy here. Just dash. Wait for him to stay still for three seconds to summon those orbs, then unload everything you have. If you have the Shaman Stone equipped, your Vengeful Spirit will do massive work here.
The Watcher Knights: The Ultimate Skill Check
If the Soul Master is about rhythm, the Watcher Knights are about multitasking. This is arguably one of the hardest City of Tears bosses because it’s a gank fight. You aren't fighting one guy; you're fighting five or six, two at a time.
A lot of players don't know about the chandelier trick. Before you enter the boss arena, there is a breakable ceiling in the hallway just outside. Go up there, cut the rope, and a chandelier falls on one of the knights, killing it before the fight even starts. It makes the encounter significantly more manageable.
You need to keep both knights on one side of you. If you get sandwiched between them, it’s over. Their rolling attacks are the biggest threat. When they bounce, you can actually walk under them if your timing is perfect, but it's usually safer to dash through them using the Shade Cloak if you’ve unlocked it yet. If you haven't got the Shade Cloak, you're in for a rough time.
Many speedrunners and high-level players like Graig or Fireborm emphasize using Desolate Dive (or Descending Dark) here. The invincibility frames (i-frames) you get during the dive animation are literally a life-saver. You can dive right as they roll into you, take zero damage, and deal a massive AOE hit to both of them at once.
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The Soul Tyrant: Returning for Revenge
Later in the game, once you have the Dream Nail, you can head back to the Soul Sanctum to fight the Dream version of the boss: the Soul Tyrant.
He’s faster. Much faster.
The Soul Tyrant is basically the Soul Master on caffeine. His orbs move quicker, he teleports more frequently, and he has a massive health pool. This isn't a fight you win by being aggressive. It’s a fight of attrition. You might only get one hit every ten seconds. That’s fine. If you try to rush him, he will punish you.
Equip charms like Mark of Pride or Longnail. You need that extra reach because he spends so much time hovering just out of range. Fragile Strength (or Unbreakable Strength) is also a must if you want the fight to end before you lose your mind.
Dealing with the Great Husk Sentry
Okay, so he’s not technically a "boss" with a big health bar at the bottom of the screen, but the Great Husk Sentry guarding certain corridors in the City of Tears is harder than some actual bosses in other games. These guys are tanks.
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They have a massive shield and a huge reach. The mistake most people make is trying to jump over them. Their upward slash is huge and will knock you back every time. The trick is to bait out their three-hit combo. Stand just close enough to trigger it, dash back, and then move in for two hits while they recover. Or, just use spells. Spells bypass their shields. A few hits of Vengeful Spirit or Shade Soul makes these guys trivial, but if you try to use your nail alone, you're going to have a bad time.
Why the City of Tears Still Matters
The reason people keep talking about these encounters years after release is the atmosphere. Fighting the Soul Master while the rain beats against the glass windows of the Sanctum is an all-time gaming moment. It’s oppressive and lonely, but the victory feels earned.
The City of Tears represents the point where the game stops holding your hand. You have to master the "pogo" (hitting down on enemies while jumping) and you have to learn when not to heal. In the Watcher Knight fight, healing is almost impossible unless you have the Quick Focus charm.
Actionable Strategies for Success
If you're stuck on any of these encounters, stop banging your head against the wall and try these specific adjustments:
- Upgrade your Nail: If you haven't visited the Nailsmith in the lower-left area of the City, do it now. A single upgrade changes the Soul Master fight from a twenty-minute slog into a five-minute brawl. You need Pale Ore for later upgrades, but the first one just costs Geo.
- The Spell Build: Most new players rely too much on their sword. The City of Tears bosses are weak to spells. Equip the Shaman Stone (bought from Salubra in Forgotten Crossroads) and use your Soul for damage instead of just healing. You'll kill bosses 30% faster.
- Farm Soul on the Follies: In the Soul Sanctum, those little floating orange blobs (Follies) spawn infinitely in some areas. Use them to fill your soul meter completely before walking into the Soul Master’s arena.
- The Chandelier: Seriously, do not forget to drop the chandelier on the Watcher Knights. It turns a 6-on-1 into a 5-on-1. It’s not cheating; it’s using your environment.
- Focus on Movement: In the City of Tears, your feet are more important than your hands. Don't look at the boss; look at your character. If you know exactly where you are in relation to the projectiles, the boss will eventually fall.
Go back in there. The City of Tears is meant to be conquered, not just survived. Use the elevators to your advantage, find the secret shortcuts, and remember that every death is just a lesson in how the boss moves. You've got this.
Once you’ve cleared the City of Tears bosses, your next logical step is heading toward the Royal Waterways or ascending toward Crystal Peak. If you haven't found the Shopkeeper's Key in Crystal Peak yet, prioritize that, as it unlocks better charms back at Dirtmouth that will make the mid-game much smoother.