Fighting bosses for the first time (or even the tenth time) in Our Darker Purpose can be quite challenging and unforgiving. Failure might be a result of bad luck but also a lack of understanding their mechanics. This guide aims to provide information about all the bosses in Our Darker Purpose, including their general movement patterns (highlighted with red arrows) and the attacks they employ (marked with blue arrows and circles). Whether you're seeking insight or preparing for the challenges yet to come, you can encounter the following bosses:

• Floors 1-3: Frothy the Dragon, Some Harmless Marking, The Box of Nice Things, Cauldron of Yesterdayers, Sudsy the Inanimate, Candelabra of Longing, The Obsolete Operator, The Frozen Few
  
• Floor 4: Goneril and the Woundworts Fortress
  
• Floor 5-6: The Disciplined King, Cyndar's Timekeeper, The Friendly Foot Stools, The Virtuoso
  
• Floor 7: Regan, leader of the Capulets
  
• Floor 8-9: The Winged Overseer, A Leafy Oversight, The Brick Pile, a Buoyant Double
  
• Floor 10: The Malady Ward, Dr. Bloodfather, Better Cordy, the Imaginaries
  
• Floor 11: The Administrators
  
• Floor 12: His Natural Defense

I'm not entirely sure if the list is correct, so please let me know if you notice any discrepancies. Additionally, I may refer to bosses by chapters (one, two, etc.). These do not correspond to the floors where you encounter them but rather to their entry in the game's lore.
In addition, I will mention changes for the bosses in Hard Mode as far as I have observed them. Please note that my information on Hard Mode changes after the Regan fight (Chapter 3+) is limited because I have not played it extensively.

This guide is complete but not finalized. I will periodically check for typos and errors in the descriptions and pictures. I would appreciate any assistance in doing the same. Additionally, I will update missing information as I obtain it. I hope this guide proves helpful in clearing the Edgewood Home for Lost Children.

Frothy the Dragon is a relatively easy boss, even on your first encounter. He has only two movement patterns, two attacks, and a moderate amount of hit points. The fight alternates between two phases.

In phase 1, Frothy moves up and down while summoning a Homing Fire that follows you (similar to the ones spawned by the oven traps). This fire spawns directly beneath you as a small orange "X," which is harmless initially, giving you a brief moment to move away.


Phase 2 begins after the Homing Fire disappears. Frothy summons multiple fires at either the top or bottom of the screen and charges horizontally across to the other side of the screen. The summoned fires will move from top to bottom (or vice versa, depending on their starting position). As soon as you see the fires appear, quickly move to the gap in the fire column and out of Frothy's path to avoid damage. The fight then returns to phase 1.

As Frothy loses health, the difficulty slightly increases. After losing a third of his health, he will summon two Homing Fires instead of one. After losing another third, he will summon three Homing Fires. Overall, the fight should not be very challenging.


Notable Hard Mode Changes: The only difference I spotted is that the Homing Fires are moving faster, a LOT faster. Avoid standing still.
Edit 08-05-2024: Additionally, the gaps in the moving fire walls are substantially smaller.

Some Harmless Markings is another of the Chapter One bosses. Most of the time, you can stand still and nothing will happen to you. At the beginning of the fight, there are six chalkboards on the wall. Over time, the picture of a Smiley Sun gradually appears on them. Once this picture is complete, a white chalk ball will shoot in a straight line across the screen. Position yourself out of its path, and you'll be safe for the moment.
But since this would be too easy, the chalk boards have a second attack. Occasionally, one of the boards will start blinking and spawn a chalk cloud that begins following you. Keep your distance from these clouds and avoid running into the chalk balls they release. After a while, the actual boss will emerge from one of the boards, and the boards themselves will cease attacking you or spawning new chalk clouds (indicated by the changed picture on them).
Some Harmless Markings will float towards you and shoot chalk balls in your direction (unlike the boards). Keep an eye on the chalk clouds that have not yet vanished, and attack Some Harmless Markings yourself. This is the only time you can damage the boss (technically, you can hit the markings when they are moving on the chalkboards, but it's much harder to land a hit) before it disappears again and the process repeats. Overall, this fight is quite easy, as Some Harmless Markings are indeed ... pretty harmless.
Notable Hard Mode Changes: The chalk boards are spawning more clouds instead of shooting a single chalk ball, now spawning two or three times the number as before. So, standing still and chilling will not work out here.

The Box of Nice Things is a giant present box that moves up and down in a curved manner while slowly drifting towards you. So at some point, you'll need to cross its path or it will corner you (though it seems the box itself cannot harm you). In addition to its vertical movement, the Box of Nice Things summons its first presents in the form of small, teeth-like creatures that charge directly toward you. Initially, they move slowly, so you can either ignore them or eliminate them. If left alone, these creatures will disappear after some time. From what I recall, there are never more than two of them on the screen at once.
After losing a third of its health, the boss will summon its first special present: The Celebrity Chopper, a giant rose-colored axe that also flies towards you. Periodically, it will perform a rotating attack, which simply increases its movement speed. To end this boss fight, you'll need to destroy the chopper as well - as it remains even after the box is destroyed - so it's better to deal with it sooner rather than later.
After losing another third of its hit points, the boss summons the Congratulator, a hand-like creature that flies towards you like the others. However, this one has a special ability to teleport, so be mindful to where you are dodging. Furthermore, - upon teleporting - it creates six small projectiles at the place it teleports to. So you have a lot of stuff to avoid. Similar to the Chopper, you must defeat the Congratulator separately from the Box of Nice Things (Note: The appearance order of the Chopper or the Congratulator is random). Also, as if fighting and dodging the special presents weren't annoying enough, both the Box of Nice Things and the teeth-like creatures move faster as the boss's health decreases. Keep rolling (and shooting) and you'll win this fight.
Notable Hard Mode Changes: Instead of summoning only one special present at 66% and 33% hit points left, the Box of Nice Things will summon both of them. So in total, you have to defeat one Box, two Choopers, and two Congratulators. At least you'll gain a lot of experience points this way.

The Cauldron of Yesterdayers is one of the more challenging Chapter One bosses. Actually, he has only one attack but this one attack is pretty effective. The Cauldron appears randomly in one of the four pots. To maximize your hits, I recommend standing in the middle of the four pots and minimizing your movement. Aim in the direction where the Cauldron appears and wait for it to start its attack, as it stays longer in the soup pot during this phase, giving you a chance to deal damage. Despite the sheer amount of projectiles it shoots, try to remain centered and make only minimal movements to dodge.
After losing a quarter of its health, the screen shakes, the Cauldron disappears, and soup blobs are spawned. These blobs move towards the last pot the boss occupied. If they reach it, the boss regains a significant amount of health for each blob absorbed, so it's crucial to eliminate them quickly. After dealing with all the blobs, the Cauldron reappears, and the fight resumes. It summons new soup blobs at 50% and 25% of its health. The most challenging phase begins after it loses half of its hitpoints: a Second Helping, resembling the boss but with fewer hitpoints, joins the fray and performs the same attack pattern, doubling the fun of dodging.
At this stage, maintaining focus is crucial to avoid taking hits while remaining centered. Since the Second Helping has fewer hitpoints, it's advisable to eliminate it first to reduce the number of projectiles on the screen, unless you're aiming for the specific boss achievement. However, since defeating the Cauldron of Yesterdayers concludes the fight, you can largely disregard the Second Helping thereafter (it seems you have to defeat the Second Helping after defeating the Cauldron; perhaps I misremembered this detail). Stay composed and focused, and you'll eventually defeat this boss as well.
Notable Hard Mode Changes: Similar to the previous boss fights mentioned, there's only one change here as well. After losing half of his hitpoints, instead of spawning the Second Helping, he spawns both a Second AND a Third Helping (trippling the dodging fun).

Sudsy the Inanimate is quite similar to Frothy the Dragon, albeit slightly more challenging. Sudsy moves up and down along one side of the screen. After a brief period, he spawns an ice block at your current position, so keep moving. Ideally, try to position yourself so that the block appears above or below Sudsy, as he will take damage each time he hits it. Additionally, Sudsy summons an ice ball that bounces off the walls and the ice block.
After a few seconds, Sudsy the Inanimate spawns a blizzard that travels horizontally from left to right (or vice versa), damaging everything in its path. To protect yourself, take cover behind the previously summoned ice block. Following this, Sudsy charges horizontally across the screen, similar to Frothy. As he charges, the bouncing ice ball explodes, sending eight ice shards flying in different directions. Dodging Sudsy and these ice shards simultaneously can be tricky. Unlike previous and subsequent bosses, Sudsy does not increase in difficulty as his health decreases. And so another boss will be put to rest by your hands.
Notable Hard Mode Changes: Sudsy undergoes two changes in Hard Mode. The first change is somewhat beneficial: he spawns two ice blocks instead of one, providing a larger area for cover during the blizzard attack. If managed correctly, both blocks can also damage Sudsy. The second change, however, adds a new challenge: he summons a second ice ball (great surprise I know) which is less helpful and more annoying.

The Candelabra of Longing is a strange fight. The boss has only one attack and a rather simple movement pattern. He is circling up and down the screen in a kind of elliptic way. Every circle differs from the one before but overall you will always have a good grasp as how the Candelabra is moving. During its movement, it shoots up to four small green flames in your general direction, making dodging trickier as the flames spread out to cover more area. However, the real difficulty in this fight stems from two other factors. Firstly, the floor is littered with caltrops, requiring careful attention to your movements to avoid taking damage. The second, more troubling issue is that most of the time, the room will be pitch black, with only the area around the Candelabra illuminated. This leaves you with two options:

1. Stay close to the Candelabra, matching its movement while dodging the green flames and caltrops on short notice.
2. Keep your distance, but lose constant visibility of the exact position of the caltrops.

You can memorize the position of the caltrops in a small area, but with the constant barrage of green flames, precise movement and dodging become challenging. Additionally, the Candelabra has one of the highest amounts of hit points among the early bosses, making this one of the more difficult encounters in Chapter One.
Notable Hard Mode Changes: The Candelabra of Longing will periodically summon a blue caltrops dropper that moves around, throwing additional spikes on the floor. This adds to the danger of moving in the darkness. On a positive note, you can eliminate these caltrops droppers like normal enemies, although their high summoning rate reduces the time available to focus on the boss itself.

If you want to call it that, this encounter marks the first Story Encounter in the game. Without fail, on floor 4 of the Edgewood Home for Lost Children, you'll face Goneril. Known for their strength and bravery, the Woundworts spend most of the fight hurling stones hiding inside the buildings. Since these stones travel straight towards your current position, you can dodge most of them with careful movement. The upside is that you can destroy every building (though it's optional). For practicality, get accustomed to demolish the building in the upper right corner first AND fast. Periodically, it launches balls in your direction, which are less annoying in normal mode but will be in Hard Mode.
At the bottom of the room, there are three identical cabins that not only hurl stones at you but also release chalk clouds that chase you. Destroying each cabin causes it to spawn two clouds, which roam randomly in the lower part of the room and persist until the end of the fight (see last picture). In the upper left corner, there's another cabin that sporadically spawns a collared Brogg. Destroying this cabin results in two additional collared Broggs appearing
Similar to the cabin in the upper left corner, the main building - the fortress - will sporadically spawn a Woundwort. When the fortress reaches 25% health, Goneril leaves it and begins attacking you directly. It's advisable to destroy the fortress afterwards swiftly so you can focus solely on Goneril (and the clouds at the bottom). Goneril exhibits three attack patterns. In the first one, she moves straight towards your position and maintains this trajectory until she transforms into herTornado form. During this time, position yourself and to win distance if necessary. In her Tornado Form, Goneril will pursue you closely and mimic your movements. Her final attack involves leaping high into the air (off-screen), then landing at the spot where you were when she began her jump (so be sure to move away from that location). Upon landing, she generates a circle of sparks that fly outward in all directions. Additionally, Goneril increases in size as she sustains more damage. As the first story fight, there are numerous elements to pay attention to, which can overwhelm players the first time they get there. The positive aspect is that the fight becomes easier over time as the screen clears with each building you destroy (which you should do unless aiming for the achievement). And with that, Goneril, the leader of the Woundworts, is defeated. Next up are the three floors leading to Regan.
Notable Hard Mode Changes: The most notable change is that instead of the small one-time balls, the building in the upper right corner now shoots spiked balls at you, which do not disappear. The longer you take to destroy the building, the more balls will accumulate, so it's crucial to destroy it quickly. Even if you manage to destroy it before it shoots the first one, it will still spawn two spiked balls upon destruction, adding to the challenge. Another change is that the cabins on the bottom side not only spawn normal chalk clouds but also green ones, which move faster and confuse you. Upon destroying these cabins, they will spawn an additional Woundwort for you to kill. Lastly, Goneril will pull you in towards her briefly after she lands, making it harder to evade the sparks from her jumping attack.

Although the Obsolete Operator is one of the chapter two bosses, you will only encounter him on the floors 1-3. But only after beating Goneril at least once. This isn't much of a problem since he is also one of the easier bosses in the game. He moves slowly, allowing you to maintain a safe distance while dealing damage. Initially, he fights alone, but as time passes, he summons random Broggs through the doors. The number and type of Broggs summoned are completely random, ranging from one to five. From what I recall, he summons his minions at least twice: once when he reaches two-thirds health and again when he's down to one-third health.Other than that he seems to summon more if you take your sweet time (correct me on this one, not sure anymore).
Other than summoning help, the Obsolete Operator has just one attack that renders him immobile. He drills his wires into the ground, causing white dots to appear and rise up beneath you. When you see these dots, simply move to a safe spot to avoid taking damage. He has different formations of this attack, varying in their range, but all are relatively easy to dodge. Coupled with his low summoning rate, this is really an easy fight.
Notable Hard Mode Changes: Not too much change here. The Operator will now be able to summon certain Woundworts, Capulets and even Gifted Ones. This addition may be irritating the first time you encounter it, but overall, even on Hard Mode, this fight remains relatively easy.

Similar to the Obsolete Operator, the Frozen Few appears as a boss on floors 1-3 after defeating Goneril for the first time. The Obsolete Operator is - so far - the first boss that remains stationary throughout the entire fight, always positioned at the top of the screen. The Frozen Few has two distinct phases. In the first phase, you have a relatively open field (with various configurations) where you can freely attack him. As a defensive maneuver, he will shoot two ice balls that bounce off the edges and corners of the field, eventually returning to target you. As his health decreases, he increases the number of ice balls he shoots, up to a maximum of six (in pairs of two).

After some time, the Frozen Few will unleash a pressure wave (and several clouds) that pushes you towards the bottom of the room. Simultaneously, he constructs a maze out of ice blocks. During this phase, your goal is to navigate through the maze, closing the distance to him. The closer you get, the more challenging it becomes to dodge his attacks. Throughout this phase, he continues to attack with a cloud that travels straight from his position to yours. Once you successfully land a hit on him (primary attack only), the second phase ends. The Frozen Few pushes you back up to the bottom of the room while shooting clouds downward. The fight then resumes with phase one, and you repeat the cycle until the Frozen Few is defeated. As implied by the boss achievement, this second phase is likely timed and you may fail if you don't reach him before time runs out. Since it never happened to me there may be some kind of penalty if you don't manage it in time (someone can verify this?).
Notable Hard Mode Changes: During the fight, the Frozen Few will gradually freeze you, causing your movement speed to decrease by 15 units every few seconds. This makes dodging and navigating the maze increasingly difficult as the fight progresses. I assume if your movement speed reaches zero, the fight will end abruptly, resulting in your defeat. If not. you are an easy target and he will kill you anyway.

The Disciplined King is one of the more hated bosses in Our Darker Purposes. This is intriguing because, objectively, he shouldn't be that difficult. However, he is one of the most unusual encounters in the game. The battle begins straightforwardly. Upon entering, you can see the entire room, which is quite sparse. In the middle stands the solitary Disciplined King. Modelled after chess, the King can move only one space horizontally, vertically, or diagonally while throwing stones at you (two at a time with varying spreads). Despite being able to move in all eight directions, he almost always moves away from you, making him the ONLY enemy in the game (to my recollection) that actively moves AWAY from you.
After losing about a sixth of his health, the Disciplined King summons his first minion, a rook. True to the chess analogy, the rook can only move horizontally or vertically but can traverse the entire length of the board. It moves when you cross its path, attempting to hit you by moving into your position. If you avoid crossing its path for too long, the rook will reposition itself. Once the King loses a third of his health, he summons a second minion, a bishop, which moves diagonally with the same behavior as the rook. That's all there is to this fight. You can see everything at a glance and always have a good idea of who is moving and how.
However, with the King always keeping his distance, staying just out of your basic shooting range (though range upgrades and the ricochet upgrade help a lot), the limited space and the pieces blocking your projectiles, it creates an awful combination. As long as you stay away, you hardly get hurt. But as soon as you approach him, you're in for some pain. This battle requires patience more than most in the game. In a certain sense, it's like playing chess. If this was the intention behind the Disciplined King, then he is a design masterpiece.
Notable Hard Mode Changes: Instead of summoning just two minions, he will summon a total of four (an additional rook and tower). He summons them one at a time, but he will have all four on the board before he has lost half his health. This makes the fight even more cramped, with five enemies against Queen Cordy.

Cyndar's Timekeeper is the second boss who remains stationary throughout the entire fight. Unlike the Frozen Few, however, he is accessible for attacks the whole time. The reason he can afford to stay still is his substantial health pool - seriously, he has a lot of health. If your build is weak in terms of damage, this encounter can drag on. After a few seconds, the Timekeeper will spawn three straight lines of red gears that rotate clockwise around him. Each line has one missing gear, which is your safe spot to avoid taking damage. Additionally, large blue bubbles will appear periodically. Standing in these bubbles increases your movement and attack speed, so make sure to use them to your advantage.
Besides the rotating gears, the Timekeeper has an attack phase where he spawns single gears at your position. These gears then shoot fireballs in a straight line towards you, so keep moving to avoid them. As long as you stay mobile, this phase is fairly easy. He alternates between these two attack patterns. After losing around 75% of his health, he will spawn two sets of rotating gears, one rotating clockwise and the other counterclockwise. Although there is usually a gap in their formation, there is a chance you won't be able to dodge if the two gear lines converge on your position simultaneously. As a sidenote, ignore the green circle in the picture; it marked an invincible spot that has since been patched out. However, even without the invincible spot, Cyndar's Timekeeper shouldn't pose too much of a challenge with a bit of coordination.
Notable Hard Mode Changes: Remember those big blue bubbles that used to make you faster? Now they slow you down. Thankfully, they are smaller than before, but this adds another layer of difficulty to the fight.

The Friendly Foot Stools are not as friendly as their name suggests. The fight against this centipede-like boss takes place in a rather large room. As with many bosses, there are two alternating phases. In phase one, the centipede moves as a whole unit. In this state, the footstools can only move in four directions (up, down, left, right). The head's movement isn't hindered by the footstools following it, allowing the boss to cross over them or even make a 180° turnaround. The direction and duration of the head's movement are completely random, so just aim in its general direction and hope to hit. Note that the footstools can only be harmed by hitting the head.
In the second phase, the head stops moving, but each footstool previously following it flies through the room in all possible directions. Each footstool piece moves in one direction until it hits a wall, then bounces off similarly to the ice balls discussed earlier. Since the head remains stationary during this phase, it's your chance to get close and damage it. After a while, the footstools will rearrange back into their formation, and the head will start moving again.
That's all there is to this fight. Okay, one little information is missing. The less health points the Friendly Foot Stools have the faster they move. Actually, that is important ^^. Defeat him fast otherwise, this battle may turn out ugly.
Notable Hard Mode Changes: The change for this fight in Hard Mode seems logical and you think it wouldn't make such a large difference. However, for me, this battle has the largest leap in difficulty from Normal to Hard Mode. The only difference is that the head no longer stays still in the second phase, meaning it keeps moving around. Especially at lower health points, the footstools and the head move so quickly that hitting them feels almost like a matter of luck.

The second Story Encounter and thus the second unavoidable fight you have to do to complete the game is with Regan, the leader of the Capulets, on floor 7. The battle starts off relatively harmless. Regan floats around in the middle of a large room, moving somewhat randomly but not so swiftly that you can't hit her. Typically, she moves from one point to another and pauses for a second or two, during which she usually casts an attack.
Regan possesses three primary attacks: a triplet of violet electric sparks that curve towards you, a triplet of ice balls that shatter into three ice shards upon hitting a wall, and a double fire ring that spreads in all directions. Each attack spreads slightly, with more distance from the origin resulting in greater spacing between projectiles.
After losing a quarter of her health, Regan splits into three entities: one retains the original appearance, while the others are coloured blue and purple. Each Regan now uses only one attack: the original continues with the double fire ring, the blue one uses the ice balls, and the purple one employs the electric sparks. And while knowing which Regan attacks you how is nice, it doesn't help since from this moment the screen is cluttered with projectiles. Adding to the challenge, only the original Regan can be damaged, and she is the most difficult to approach due to the 360° radius of the fire attack. But do not fear, Regan can still become worse.
Actually, it depends; I find her last phase in some regards easier than the one before. After losing around two-thirds of her health points, she changes her attack patterns. The purple Regan starts shooting big spark balls that follow you everywhere. They can suddenly change direction, even up to 180°, but there's a slight delay. If you dodge them near a wall, they'll hit it and release small sparks. It's best to let them hit the wall early because the longer they fly around, the faster they move.The blue Regan creates ice blizzards that sweep horizontally across the screen, making vertical movement riskier and further cluttering the screen. Meanwhile, the original Regan summons fire spots marked by red X's on the battlefield. These spots burst into fire randomly and stay (for a change) stationary. Thus, this attack is less dangerous than the fire rings since it's now easier to approach the original Regan.
It may be challenging, but keep your eyes open during the fight and pay attention to every detail. With perseverance, you can defeat her. Although the first time I fought her, I thought the same: You must be kidding, right?
Notable Hard Mode Changes: How could you make this fight possibly harder? Right, add one more Regan - a white one. This new Regan summons little tornados that charge through the room at a fast pace, adding more stuff to dodge. Enjoy the chaos!

Edit 08-05-2024: Small addition: In the second phase of the fight, White Regan summons just one tornado, but in the last phase, she summons two tornados.

For most people, encountering the Virtuoso will be cause for celebration, as he is one of the easiest bosses and can be beaten with a bit of concentration without taking any damage yourself. Upon entering the room, you'll immediately see the whole room with the boss occupying a large portion of the upper side.
The boss has only two attacks. The first one being purple notes flying in your direction. While these notes don't cause damage, they can confuse you, so it's best to avoid them. They move slowly, and if you stay at the bottom of the screen, they usually won't reach you. However, when combined with the boss's second attack, they can become more annoying. The second attack are hands emerging from holes in the ground trying to grab you. Unlike the hands in the floors, these follow a predictable sequence, which is telegraphed in advance. You'll always know one or two seconds beforehand where they will appear, so use this time wisely to evade them. There are two patterns:

- Wave-like from left to right or vice versa.
- Block-like on either the left side, right side, or both sides.

After losing a quarter of his health, the chair in front of the boss begins to move left and right, obstructing your attacks. This poses a problem because you can only damage the Virtuoso at his central part. You'll need either a lot of patience or, if you can spare some chalk, get close to the flying chair and use a cloud, as it will destroy the chair on contact, leaving the boss defenseless.
Notable Hard Mode Changes: In addition to the single purple notes, he will also attack with larger note clouds. This requires you to dodge more and adjust the timing of your movements. Still one of the easiest bosses, even in Hard Mode.

This is one of the few boss battles in the game where having fast movement really pays off. As soon as the fight with the Winged Overseer begins, you'll notice two things. First, there's an ever-changing wind in the room that disrupts your precise movement. Second, there are numerous eggs scattered around the room that will spawn small white birds when touched by the Winged Overseer, you, or your attacks. These eggs occasionally respawn. The Winged Overseer hovers over a spot in the room and sends a triplet of red birds at you: the middle one flies directly toward your position, while the other two fly above and below it. You can either keep your distance and try to pass through the gap between the birds, or stay close to the boss and roll around all three of them.
Note that the Winged Overseer always faces you, ensuring the middle red bird flies directly at you. After releasing four or five triplets of red birds, the Overseer will leave the room, flying in your direction. You can position yourself to make the Overseer take a longer route, allowing you to damage him during this phase (but be quick, as contact will harm you). Once the Overseer exits the room, a marked line will appear on the ground, and the boss will charge over it, damaging everything in his path (including you and the eggs). He will do this 1-3 times before resuming his initial attack pattern. It's important to note that the span of the Overseer's charge is larger than the markings on the ground, so you can still be harmed if you are too close to them. Also, during the charging phase, there will be no wind, allowing you to move normally.
The Winged Overseer is usually of moderate difficulty. However, if you're lacking area attacks or roll items, the white birds can become a serious threat. Other than that, happy bird hunting!
Notable Hard Mode Changes: I have to think if I ever fought the Winged Overseer in Hard Mode, but I can't recall any notable changes. If you read this and know of any, please tell me. It may be that he shoots not three red birds but five, but I can't say for sure. Another possible change could be that the little birds have more health, making them harder to kill than before.

Edit 08-05-2024: The Winged Overseer shoots five red birds instead of three.

After the Frozen Few, Cyndar's Timekeeper, and the Virtuoso, we have our fourth boss who doesn't move an inch throughout the fight: the Leafy Oversight. As often, it begins quite easily with the Leafy Oversight positioned on the right side of the room. He shoots what I will call spiked spores at you, three at a time, similar to the Winged Overseer. However, the spread of this triplet is slightly larger, allowing you to stay within attack range and still dodge the spores effectively. Like before, the middle spore of the triplet flies straight at you. Additionally, he will spawn flower seeds that slowly drift to the left side of the screen.
You can and should destroy these seeds because, after drifting far enough, they will plant themselves in the ground, grow into flowers, and start attacking you with more spores. The more flowers there are, the harder it becomes to dodge, leaving you with little time to attack the Oversight. To ramp up the difficulty, the boss will spawn more flower seeds as his health decreases, up to six at a time. Destroying all the seeds while still finding time to fight the Oversight can be tricky.The real danger, however, appears if you can't kill the flowers fast enough. They will revert to a flower seed (with a slightly different color) and drift back to the boss. In this phase, you can't destroy them anymore. As they reach the Leafy Oversight, he will absorb them, making his attack not only faster but also increasing the number of spores (up to seven in the last picture, possibly more) and narrowing the gaps so you can't dodge through them anymore. To make it worse, the boss has rather high health.
Without a certain damage output, this fight will be nearly impossible to win, making it one of my most hated bosses in Our Darker Purpose. On the bright side, if you have enough chalk to spare, you can get in front of the Leafy Oversight (when it’s low on health) and attack with the chalk. The clouds will block the spores and damage the boss while you remain unharmed. Timing this strategy between the boss's remaining health and your chalk supply can be tricky. Also, ignore the tornadoes in the pictures - they are from my build at that time.

EDIT: Other players have reported that you can destroy the flower seeds by walking into them, which will only confuse you. I have never tried this myself, so proceed at your own risk. It could make the fight a bit easier.
Notable Hard Mode Changes: I really struggle to remember the changes for the later bosses. The Leafy Oversight obviously has more health and moves faster in Hard Mode. Additionally, he takes the flower seeds back to himself much quicker. The movement speed of the flower seeds to and from the Oversight is also faster.

EDIT 08-05-2024: Generally, it’s a more aggressive and faster fight. The Leafy Oversight shoots faster, generates new seeds faster, and reabsorbs them quicker.

The Brick Pile is one of the easier bosses. While a bit reliant on luck, you can generally win this fight with only some minor scratches or no damage at all. Once the battle starts, the Brick Pile will pursue you. Periodically, it will pause briefly and throw bricks at you (in pairs of two). These bricks will shatter upon hitting the wall, sending stone shards flying in three directions based on the impact angle. To minimize the risk of getting hit by these shards, ensure you have sufficient open space behind you.
After losing 25%, 50%, and 75% of its health, the Brick Pile will crumble and spawn mini versions of itself. The lower its health, the more mini versions appear, up to eight (?) at 25% remaining health. These mini piles will move around the room randomly and eventually explode, creating eight stone shards that fly in different directions and spawning three green blobs. Since the movement and explosion timing of the mini versions are unpredictable, this phase of the fight is the trickiest. With so many mini piles, they can quickly corner you, and if they explode close to each other, you could face 20-30 projectiles on the screen at once.
So, you need a bit of luck to avoid taking damage. However, if you maintain your distance, you'll rarely get hit. Now, regarding the green blobs: similar to the Cauldron of Yesterdayers, these blobs move towards the Brick Pile to heal it upon contact. Unlike the Cauldron, the healing amount is not significant, so it's often safer to let some blobs reach him rather than taking risks to stop them. Nonetheless, it's still preferable to eliminate them. Once all the mini versions and green blobs are dealt with, the Brick Pile will resume chasing you. As mentioned earlier, the Brick Pile is not a difficult boss but can be quite annoying.
Notable Hard Mode Changes: I fought him in Hard Mode definetely. But here aswell I can't remember any notable changes. If you have some please post them in the discussions.

The Malady Ward, also known as Specialist Fenwick, is a peculiar boss because he doesn't seem to pay any attention to you. He doesn't follow you or actively attack, and I'm not even sure if he can hurt you. Additionally, you can't damage him all the time. So, how does this fight actually work?
Besides the Malady Ward, numerous puppets are on the screen. These puppets chase you and throw red fire-like attacks in your general direction, though not in a straight line. And since the projectiles reflect off the walls, they are unpredictable and widespread. This unpredictability is enhanced by the fight taking place in the dark, with only two spots illuminated: you and the boss.
The puppets are the ones that can damage you, and you can damage them as well. Once you've hurt them enough, they become unconscious, prompting Specialist Fenwick to run towards them to heal them. During this healing process, you can deal damage to the actual boss. Otherwise, damaging Fenwick is not possible in this phase. Therefore, focus on taking out the puppets quickly and as many as possible, then attack the boss while he heals them.
After a while, the phase changes. All puppets will fall unconscious, and their ghost bodies will rise, continuing to attack as before, but with some changes: First, the only illuminated spot will be the boss. Second, you cannot hurt the puppets in this phase. Third, and most importantly, you can damage Fenwick continuously. This is the phase where you can actually battle and defeat the Malady Ward. Although the screen is mostly dark and the action is intense, the fight isn't overly difficult. Since the room is rather large, roll around and avoid the attacks until the second phase. Then, focus on getting close and defeating the boss.
Notable Hard Mode Changes: The same as before. If you have information provide them to me please. Based on an user comment, it seems they Malady Ward can heal all downed puppets at the same time.

Among the library bosses, Dr. Bloodfather is arguably the most formidable and challenging. In addition to him, there are green-colored puddles on the screen. Periodically, these puddles spawn bats that are sent straight at you - simply roll out of their path.
Dr. Bloodfather himself transforms into a red-colored puddle and chases you for a few seconds. When he stops, he reverts to his form and unleashes a barrage of bats with a wide spread and no gaps between them. Rolling backward won't help you evade this attack. Maintaining a larger distance is also not advised, as the wide attack spread increases the likelihood of getting hit. Instead, it's better to stay close and dodge to the side the moment he begins the attack. So get your timing right.
In addition to his puddle form and normal mode, Dr. Bloodfather can transform into a giant bat surrounded by numerous smaller bats. Unlike the previous bats, these smaller ones can and must be eliminated. As the giant bat boss chases you, it releases the smaller bats in all directions, each capable of dealing a LOT of damage upon contact. Having area-of-effect attacks or ice shards can simplify this phase considerably. The phase only concludes after all the small bats are dispatched.
While in his giant bat form, the boss cannot be damaged (and I'm unsure currently if the puddle form is vulnerable). The sheer number of bats and the boss's large area attacks make this fight quite challenging. Oh, and one more thing: once Dr. Bloodfather has lost half of his health, the screen turns red, and you begin losing hit points continuously, even if you avoid being hit directly.
Notable Hard Mode Changes: I can't recall any changes, so please share them if you've noticed any.

Edit 08-05-2024: The life-drain effect intensifies during the second half of the fight, draining more health per tick.

A Buoyant Double is like a giant balloon in Cordy-form. And like a balloon her whole movement is floaty. She is moving rather slow has no sharp cuts and behaves inertly. At the start of the fight, she summons four mini-versions of herself that orbit around her while she pursues you. When you destroy one of these mini-doubles, it explodes, spawning eight ice shards that fly outward in straight lines in eight directions.
After a short while, she transforms any mini-double you haven't destroyed into small whirlwinds. These whirlwinds move randomly and quite quickly, posing a challenge to dodge. While these whirlwinds are active, she summons another four mini-versions that rotate around her. Additionally, she summons a total of eight doubles, which appear either at the top or bottom of the room in various formations. Those at the top move downwards, while those at the bottom move upwards. If they converge in the middle, they form a complete line, restricting your movement space temporarily. To manage this, you must dodge them before and after they reach the middle. Or you just destroy one or two of them to alleviate the space constraint. Once these eight mini-doubles vanish, the Buoyant Double transforms the remaining ones rotating around her into whirlwinds.
Overall, because all the doubles move relatively slowly, this fight isn't overly difficult if you plan your movements ahead. The main challenge lies in avoiding the unpredictably moving whirlwinds.
Notable Hard Mode Changes: Need information here, since I didn't note any changes. If you have information please provide it, so it can be added.

Edit 08-05-2024: The Buoyant Double now surrounds herself with more mini-versions. Instead of four, she can have up to ten mini-versions rotating around her, leaving no gap to shoot through.

This fight can be quite familiar because Better Cordy is like you .... just better. Although it depends on your build. As you can see rather fast the room is pretty small which is normally an instrument to make sure that the attacks of the boss connect. The second thing you will notice are the hearths at the top of the room. These are identical to the ones found on lower floors and shoot a triplet of green flames with a slight spread. Don't be confused if they're absent in later pictures - I destroyed them (you need a specific lesson or perk for this).
Better Cordy will relentlessly chase you around the room, firing two projectiles simultaneously - a skill you never learned. This, coupled with the 20-30 green flames from the hearth, creates a barrage of projectiles to dodge. Additionally, Better Cordy can summon purple chalk clouds, unlike your blue ones (and other enemies' white and green clouds). Although I haven't personally observed it, she is also rumored to use a juice box to heal herself, potentially up to three times. And this is basically everything.The main challenge of this fight lies in the cramped quarters and the sheer number of projectiles to avoid. Keep your distance, dodge and attack yourself. At this point in the game you should have a more powerful build than Better Cordy.
Notable Hard Mode Changes: Remember that awesome item that lets you spawn fire while rolling around? Well, now Better Cordy has it too, further restricting your movement in the already cramped room.

The Imaginaries present an intriguing concept for a boss fight, although they end up being too easy. But increasing their power only slightly could potentially make them a significant annoyance and possibly overpowered. The core mechanic of this fight is that you do not take damage; instead, getting hit reduces your movement.Upon entering the room, you'll notice numerous stone statues. The layout of the room will always be the same, with only your own light and the boss's flame attacks illuminating the area. These green flames move in straight lines to a designated spot, pause briefly, then continue along another straight path to a new location. The direction they move after pausing is random. If one of these flames hits you, you'll lose 15 movement points. Although I haven't experienced it personally, reaching zero movement would likely result in a game over or force you to quit since you'd be unable to move anymore.
In this fight, your objective is to locate the green stone statue, as it's the only way to damage the boss. The green statue's position changes every few seconds, requiring you to continually search for it. Once the Imaginaries lose half of their health, they introduce a new attack similar to Frothy's fire. This attack spawns under you and slowly follows your movements. Normally, this fight is quite easy and offers the significant advantage that you won't expend any juice boxes or health in general.
The only time I struggled with this boss was when I was hit multiple times before finding the green statue for the first time. As your movement slows from being hit, it becomes increasingly difficult to reach the next statue position.
Notable Hard Mode Changes: I did not note any changes. If you have experienced otherwise please provide me with information.

On Floor 11, you encounter the third Story boss, the Administrators. They are giant human-like paper creatures that begin chasing you as soon as the fight commences. Periodically, he pauses to create a red portal from which red-colored paper sheets attack you. The Administrators continues chasing you while spawning a second portal. Eventually, he disappears, signaling the start of the second phase of the fight.
The annoying thing is that the administrator can not be damaged in this second phase since he is nowhere to be found on the screen. Instead, a number of black portals appear based on the Administrator's health (ranging from 4 to 8 as health decreases).
To progress to the next phase, all portals must be destroyed, one by one, starting with the portal attacking you with red paper sheets.Since the room is dark, you must rely on the trajectory of the attacks to identify the correct portal. Each incorrect shot spawns an additional enemy, adding to the challenge. The portals also unleash random attacks from various enemies in the game, so careful targeting is crucial. Once you destroy the correct portal, the red sheet attack moves to the next portal. After successfully navigating through numerous attacks and destroying all black portals, the Administrator reappears. Use this opportunity to inflict damage and defeat them, allowing you to proceed to the final challenge.
Notable Hard Mode Challenges: Occasionally, four additional Administrators appear in a rhombus formation during the battle. These Administrators cannot be damaged and their sole purpose is to initiate a paper storm attack. This attack spawns white-colored paper sheets that fly across the screen, adding to the challenge of the fight.

DO NOT STOP MOVING. Ahem. On Floor 12, you face His Natural Defense, the final encounter in the game (the final known encounter). This boss is a giant squid-like paper monster where halting your movement can lead to failure. His Natural Defense relentlessly pursues you, attacking with a barrage of fast-moving red paper sheets. Attempting to dodge backward only increases the distance between you and the boss, so circling around him is recommended. In addition to direct pursuit, the boss can teleport short distances, appearing suddenly to your left, right, or any other location. This ability requires quick reflexes to maneuver around unexpected movements. When not teleporting, His Natural Defense creates three rings of paper sheets around itself, restricting your movement. Remaining within these rings makes dodging the red paper sheets nearly impossible. However, staying outside the rings often puts you too far away to effectively damage the boss in most cases.
To make the fight more fun His Natural Defense can summon all kind of enemies (behaving like their counterparts on other floors) directly under you without warning. Constant movement is crucial to avoid being caught off guard by these sudden appearances. Once the boss loses half of its health, paper waves start appearing. These waves move swiftly from one side of the screen to the other in a wave-like pattern, posing significant damage potential and cutting off potential escape routes. Despite the room's considerable size (though not limitless, its boundaries are rarely visible), it's easy to lose sight of the boss. In such cases, His Natural Defense can reset the room, teleporting you to the center and reappearing shortly after.

While His Natural Defense isn't the most challenging boss in history and is considered of normal difficulty compared to others in the game, its versatile attacks have a high probability of hitting you. Therefore, the key advice remains: DO NOT STOP MOVING.
Notable Hard Mode Changes: Well, not that you have much time to notice any changes and one would think that the increased damage of Hard Mode should make this already enough (especially for a No Juice Run). However, His Natural Defense now teleports at a higher rate, making its movements even more unpredictable. Coupled with an increased spawn rate of minions, this means you'll find yourself running around. A lot.

6. Final Remarks
And that concludes my fourth guide. Please let me know how I can improve the wording of certain phrases; I feel some of them sound awkward. If you spot any mistakes (spelling, grammar, or content-related), please leave a comment so I can correct them. This project took longer than I initially expected. Who the hell created 24 freaking boss battles anyway?

So as final words:
Thank you for reading