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This guide will show you all secret achievements and has a short explanation how to get them. You might want to avoid reading if you don’t want to spoil the surprise for yourself!
That’ll do, pig…
Lose a hero to Wilbur
Wilbur will appear alongside the Swine Prince. Wilbur’s attacks are very weak so this might be tricky. It is much more likely that the Swine Prince kills your heroes, so deal with him first, with the boss killed the mission will not count as complete failure if all your party is killed.
When alone, Wilbur will attack with Squeal, it will hit all your party with 1-2 damage and has a chance to stun. Don’t use any heals and just wait until he kills something. Avoid passing the hero’s turn, as it will give them some stress. Some afflictions may cause them to attack Wilbur. Just shift their positions and wait for a killing blow.
We return to the worms of the earth…
Lose a hero to a Maggot
Maggots are probably the weakest monster in the game, both in DMG and HP. The easiest way to do this is take four heroes of resolve level 0 and throw them into the Ruins. Eventually you will come around a Battle with 4 Maggots, just let them attack you freely. The tricky part is that the Maggots attack with Grave Nibble, causing both stun and stress. Try using weaker classes so they get killed easier. I suggest bringing Jesters, since they don’t have many HP and their Inspiring Tune will prevent the heroes from getting afflicted.
Blocked from life…
Lose a hero to an obstacle
Eventually you will find an obstacle that hinder the party’s movement along the path. Don’t bring any shovels and clear the obstacle by hand, doing so will damage the heroes and increase their stress. As you depend on chance, you might have to try this multiple times.
The hero must already be at Death’s Door to get killed by the obstacle.
Watch your step…
Lose a hero to a trap
Eventually you will encounter traps in the path, either by setting them or scouting them. If you scout them, just walk over them to trigger the trap. Each hero has a different 
Trap Resistance, the lower it is the more likely they are to get hit by the traps. As you depend on chance, you might have to try this multiple times.
The hero must already be at Death’s Door to get killed by the trap.
Valiant sacrifice…
Lose all four heroes on a Darkest Dungeon quest
Arguebly the easiest one, all you have to do is pick 4 heroes, send them into the Darkest Dungeon and keep going until they all get killed.
Use heroes with resolve level 0, doing so will also give you the Like lambs to the slaughter… achievement.
Getting killed
To increase your chances of getting killed, try to:
- Use no torches, the monsters will hit harder
- Bring less or no food
- Use the Book of Holiness or Gambler’s Charm trinkets: -6 Death Blow Resist each
- Use heroes with the Weak Grip on Life quirk: -10% Death Blow Resist
A terrifying figure emerged from the darkness…
Slay a Shambler
The Shambler appears as a hallway fight with a very small chance in total darkness or when a Torch is used in a Shambler’s Altar (which instantly reduces light to 0). It is an Eldritch mini-boss that drops Ancestral Trinkets when killed.
Behavior
The party will always be surprised when encountering a Shambler. If summoned from an altar, the Shambler will automatically bring the torchlight down to 0 and will prevent the party from lighting torches while fighting it. If you run away from it, the Shambler will appear again as the next encounter. DO NOT summon it unless the party is ready to kill it. Due to a very low SPD, it most likely will act last, using its bleed or blight attack and summoning 2 Tentacles.
Tentacles have a very high SPD, they are very likely to take actions before the party, applying a strong buff of PROT and DMG to themselves. If one or both of Tentacles are killed, Shambler will re-summon them, if both left alive he has a chance to use Stentorious Lament, messing the party’s formation.
Strategy
Shambler is very strong, stronger than some bosses. Most of the times it would be a right choice to pass on the opportunity to fight him. If you decide to summon him, its better to return after you completed the quest objective to do so, because your party most likely will be in no condition to continue the expedition after the encounter with the Shambler.
It’s important to finish the fight as soon as possible. The general strategy is to kill Tentacles and stun the Shambler to prevent it from re-spawning them. If you don’t have a reliable stun, leave 1 Tentacle alive. Using Marks, you can ignore the Tentacles and finish the Shambler quickly. High bleed and blight resistance is encouraged.
Also, darkness bonuses (such as Moon Cloaks or quirks like Lurker) are worthwhile as you will be fighting with no light
Assembling your party
- Abomination: due to his high speed, can kill both Tentacles with Rake before they buff themselves
- Arbalest: synergizes well with any hero, can Mark and hit the Shambler when it is in rank 3 or 4
- Bounty Hunter can stun it and apply Mark
- Crusader: can take care of both Tentacles with Zealous Accusations
- Hound Master: can reduce Shambler’s PROT and Mark it
- Occultist: does increased damage vs. Eldritch, can apply Mark and Weakening Curse, reducing the enemy’s damage
Note: the champion difficulty Shambler is much stronger than the other variants.
Murder of Crows
Kill the Shrieker
The Horrid Shrieker appears in two random Town Events. It is an Eldritch/Beast mini-boss that drops Shrieker Trinkets, surviving heroes may also receive several unique perks. It is accompanied by its Nest.
Behavior
The Shrieker has attacks that move it forward and backwards, deal strees and apply debuffs while giving itself buffs. It also has very high DODGE, even with accuracy boosts you’ll likely only have between 40-60% chances of hitting it. For the Shrieker’s last turn in Round 4, it uses Shrieking Flight, dealing stress damage to all heroes and flying away, ending the battle.
With the exception of Peck and CRITS, the Shrieker’s attacks only deal 2 damage. Because of this try to buff your DODGE status. Its one offensive move, Peck, deals heavy damage and can cause bleeding.
The Nest does nothing, its only function is to protect Shrieker by keeping it out of range of melee attacks.
Strategy
The fight starts as soon as you enter the zone, so no boosts from Camping Skills here. Bring many Bandages and Herbs to cure your heroes, some Holy Water too as it can be used in battle. Also, radiant light bonuses (such as Sun Rings or quirks like Photomania) are worthwhile as your torch won’t go down at all unless you douse it yourself.
It is recommended to ignore the Shrieker and focus on the Nest. The Shrieker drops no loot upon dying, but the nest will drop Puzzling Trapezohedrons, maybe a Journal Page and lost Trinkets, if you have the mission from “A Thief in the Night” town event.
Assembling your party
- Arbalest: can Mark and hit the Shrieker when it is in rank 3 or 4
- Bounty Hunter can stun it and apply Mark
- Hellion: can hit front and back row
- Hound Master: can and apply Mark and does increased damage vs. Beast
- Jester: can buff your party’s ACC and CRIT
- Man at Arms: can buff your party’s ACC and DODGE
- Occultist: does increased damage vs. Eldritch, can apply Mark and Weakening Curse
Note: the Horrid Shrieker only appears as a Champion level mini-boss.
Mine Goes to 11
Kill a Squiffy Ghast with a Jester
The Squiffy Ghast is an enemy that can only be found in Champion level Cove dungeons. The Squiffy Ghast starts battles off in the back ranks. It will first use Maddening Shanty to move itself to the front. On its next turn it will use Offkilter Jig to send itself to the backlines while inflicting Horror on your heroes. This is a unique status that deals 5 Stress damage for the next 4 rounds.
Your best chance to kill it is to damage it a little with other heroes and finish it using Finale. If the Squiffy Ghast is in the front, try to stun it before it can attack.
The Crimson Court
The Flesh is Willing
Recruit a Flagellant.
The Flagelant is the new hero class in the DLC, he can be acquired at the Stage Coach at random or by a Town Event.
Symptoms
Get Infected by the Crimson Curse.
Probably the simplest one, Bloodsucker enemies from the Courtyard have a chance to inflict The Crimson Curse while attack.
Happy Together
Complete your first Trinket set
Special Trinkest that, if used together, give an extra bonus. Each class has an unique set. They can be obtained in the Courtyard and Crocodilians will always drop one trinket.
From Rubble To Rabble
Build Your First District Building
A Town Even will unlock districk building. You’ll need Blueprints to build districts, which are dropped by bosses.
The Red Hook
Build The Red Hook
A district with no purpose other except proclamation of one’s dedication.
An Unexpected Party
Collect the Invitation
After the first Crimson Court quest, the first “infestation” of the Estate will begin. Courtyard monsters will begin to appear in other regions. When the infestation level reaches HIGH, you will start to encounter Gatekeepers. The Gatekeeper, if killed before he can escape, will drop an Invitation. Each invitation allows one entry into a new Courtyard boss quest.
An Unexpected Party
Les Jeus Sont Faits
The greatest challenge is not the Baron himself, but the dungeon he resides in. It is a an Epic sized dungeon with nearly a hundred rooms and many locked gates requiring special keys looted elsewhere inside the dungeon and guarded by powerful foes. The dungeon itself can be split into four distinct areas, with the Baron residing in the final area.
Just The Cheque
Defeat the Viscount
Resides in an Epic sized dungeon.
Her Last Dance
Defeat the Countess
Resides in an Epic sized dungeon.
Expired
Lose a Hero to Wasting Away From the Curse
All you have to do is not give The Blood to heroes affected by the Crimson Curse. Eventually their thirst will overcome them…
Shadows Blur Together
Kill an Ally While Under the Curse
This one is hard as you’ll have to rely on random chance. Cursed heroes who are either Craving, Wasting in Bloodlust have a chance to attack allies, appling some debuffs to them.
What Strange Bedfellows
Contract the Crimson Curse via Contagion
If you leave a Cursed hero in the Hamlet, there is a chance their curse will spread to the other heroes there.
Zealous Accusation
Defeat the Fanatic
Once two of your heroes have the Crimson Curse, the Fanatic will start to search for the curse in order to purge them. The more cursed heroes in your party, the higher the chance of him appearing.
Similarly to the Hag, The Fanatic will put one of your cursed heroes in a pyre, where they can’t do anything and will receive constant damage, he has three moves per turn.
Jailbreak
Rescue someone
Within a secret room you can find a randomly generated leveled hero who can be rescued. Upon returning to the Hamlet the hero will be avaliable at the Stage Coach.
Bloodcult
Have Your Entire Roster Affected by the Crimson Curse
It helps if your roster is small, just give it time and the Curse will spread on its own. If you really want to get this one fast, just dismiss all “healthy” heroes.