Cuphead: How to beat Esther Winchester

Join Cuphead, Mugman, and Ms. Chalice to beat this bovine baddie!

Few games are as challenging as Cuphead. While the base game is tough, The Delicious Last Course offers bosses that put those in the base game to shame. One such boss is Esther Winchester, a bovine sheriff holding on to one of the Wondertart ingredients. Not only is this fight tough, but it’s an airborne battle.

Before you battle Esther Winchester, ensure you’ve beaten the previous enemies from the DLC, including Glumstone The Giant, the Moonshine Mob, The Howling Aces, and Mortimer Freeze.

Weapons and Charms

Cuphead Weapons and Charms 2
Screenshot by Tai Hofmann

Before starting High-Noon Hoopla, ensure you’re equipped with your preferred charms when confronting Esther Winchester. Because this is an airplane battle, only the charm you take will matter in this fight.

  • Charm: Astral Cookie

We recommend using the Astral Cookie to take control of Ms. Chalice for this fight, as her plane’s weapons are excellent against this adversary. You’ll get this charm when you start The Delicious Last Course.

Related: Cuphead: How to beat Mortimer Freeze

First Phase

As mentioned above, you’ll pilot an airplane during Hi-Noon Hoopla. You’ll use your aircraft to fight this boss as with other airplane levels. You’ll have increased mobility and different weapons than usual, so feel free to take a few tries to acclimate to the controls.

Ms. Chalice has a unique set of abilities in her airplane, shooting a spread shot as her primary fire while her secondary fire shoots smaller bombs. Because Ms. Chalice controls differently than Cuphead and Mugman in the air, adjusting to her impressive but unique move set may take some time.

Cuphead Esther Winchester Phase 1
Screenshot by Tai Hofmann

In phase one of the Esther Winchester battle, Esther pokes her head out of a rolling saloon, shooting Snake Oil out of two cans. Esther can spawn in either the top or bottom door of this moving building. During the first phase, Horse Flies will fly in and aid her. Watch out for these little critters and the projectiles they fire.

Cuphead Esther Winchester Snake Oil Parry
Screenshot by Tai Hofmann

Watch for the Snake Oil’s second attack during the first phase as the projectile loops around and turns into a snake before hurtling across the screen. Make sure to use your Shrink ability if the airspace seems crowded. Keep in mind that shrinking does alter the airplane attack, changing the fire mode to small, short-ranged bullets. We suggest shrinking when overwhelmed but returning to normal once the airspace clears.

Players can parry some of the Horse Fly projectiles, so look for pink ones. Hit these when you can to fill your super meter quickly.

Cuphead Esther Winchester Cactus and Horsefly
Screenshot by Tai Hofmann

Esther also lassos a giant cactus towards the Saloon during the boss battle. When you hear her yell, ‘Yee-haw, ‘ head to the opposite Saloon entrance, as this attack covers the area horizontally. Esther can rope the cactus towards her on both the top and bottom levels.

When Esther inhabits the bottom level of the Saloon, we recommend swapping to the secondary fire. Drop bombs on her from above while avoiding attacks like the Cactus Wrangle to expedite this phase.

Cuphead Esther Winchester Phase 1
Screenshot by Tai Hofmann

The last attack in phase one sees a Vulture drop Dynamite from above. The Dynamite breaks into three tiny shards at first, with two additional fragments following a second after the initial explosion. Take care when this minion spawns in, as the explosives travel quickly and hurt you early on.

Cuphead Esther winchester
Screenshot by Tai Hofmann

Once Esther lifts the roof of the Saloon and pulls out her vacuum, the first phase is over. Keep an eye out for the above animation.

Second Phase

Esther’s second phase is the shortest and the one with the most operating room, so take advantage of the entire level’s area to avoid projectiles. Equip the primary fire for the second phase and position yourself to avoid obstacles.

If you have a Super, get ready to use it, as this is one of the best points in the fight to hit Esther. Ms. Chalice turns into a missile that automatically moves forward during her super. Once you line up with the boss, let the super loose.

Esther Winchester Phase 2 Vacuum
Screenshot by Tai Hofmann

Esther Winchester uses a giant vacuum to suck up money bags, coins, and bundles of cash in the second phase. The pull from the vacuum will pull players toward it, so continuously pull back against the suction.

Watch out for projectiles in the air. They’ll whittle your health down if they make contact. Remember to shrink when necessary to mitigate damage. Keep an eye out for pink items during this phase, as they are parry opportunities.

Cuphead Esther Winchester Safes
Screenshot by Tai Hofmann

After Esther Winchester sucks up her cash, she’ll rain safes down from above. Avoid these items and watch out for them once they hit the ground. Each safe will explode, shooting out money and objects when they break. Some of these items are pink, so parry when you can and shrink when necessary. Keep the pressure on for Esther to end this phase quickly.

Cuphead Esther Winchester Phase 3
Screenshot by Tai Hofmann

Once the vacuum sucks up Esther, the third phase will begin, so get ready for a new move set when you see Esther processed into a walking sausage link.

Third Phase

Once the third phase begins, you’ll fight with the walking meat link, Esther Winchester. There are several new obstacles to avoid during this phase, so keep your eyes out and keep firing as she enters her penultimate form.

Cuphead Esther Winchester Phase 3 Part 2
Screenshot by Tai Hofmann

Esther will run backward on the ground during this phase, shooting ribeye steaks from her mouth that follow a circular trajectory. These projectiles move fast, so shrink down if you can’t get some distance from the boss in time. When Esther is on the ground, try bombing her with secondary fire when above. Do this in bursts, as you’re vulnerable when you get directly above Esther for too long.

Flying Acme Bean cases will also appear, with several Bean Buddies stretching out from the cans when players pass by. These enemies can spawn from the cans’ top and bottom, so watch what side the beans’ heads poke out from.

Cuphead Esther Winchester phase 3
Screenshot by Tai Hofmann

Esther can also take to the sky during this phase, hovering over the battlefield and shooting out steaks from above. Some of these steaks are pink, so parry if possible, but don’t risk your health if it isn’t within reach.

Use your primary fire when Esther is above, as bombing her would be challenging from this point. Keep your distance and fight cautiously.

Cuphead Esther Winchester Final Phase Sausages
Screenshot by Tai Hofmann

Once Esther enters the MDHR Praire Dogs Can, the final and most challenging phase has begun.

Related: Cuphead: All of the Trophies and Achievements

Final Phase

Equip your primary weapon for the last part of the Esther battle. You’ll want to keep some distance and stay horizontal from Esther when possible. If you’ve got a Super during the final phase, we recommend using them as soon as possible. Esther’s final form can be overwhelming, so the faster you take her down, the better.

Cuphead Esther Winchester Sausage chilis
Screenshot by Tai Hofmann

Esther’s final phase sees her spawn two sausage links from the front of the can. These sausage chains will alternate from the top and bottom of the screen. You’ll need to slide between the gaps to avoid taking damage. They’ll move fast and give little time to respond, so prepare to shrink to make it through these hazards.

Cuphead Esther Winchester Final Phase Sausage
Screenshot by Tai Hofmann

Esther also shoots several jalapeño peppers intermittently throughout the phase. You’ll have to back up, shrink and dodge these items. Some of these are pink, so parry if you can to build super energy. Once you have supers, remember to use them and beat this phase.

Cuphead Esther Winchester Final Phase Knockout
Screenshot by Tai Hofmann

Keep fighting carefully until the ‘A Knockout!’ message appears on the screen and seals the deal on this challenging aerial boss.

To see our A+ Esther Winchester video boss guide, check out the video below:

For more on Cuphead, including boss guides, stay tuned to Press SPACE to Jump!

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Tai Hofmann

I'm Tai, the New Games lead, Writer, and Editor for Press SPACE to Jump. My first memory is forcing my parents to play 50-round games of Mario Party on the N64. Now I love games on all platforms and hone in on new releases. Some of my favorite titles include Final Fantasy XIV, Cuphead, God of War 2018, Persona 5, and Smash Bros.

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