Wednesday, 13 May 2026

Reviewing Undertale Monsters - Part 1

Undertale is a cute, charming game released all the way back in 2015 by Toby Fox. It took the world by storm, due to a combination of its adorable 'old-school pixel game' graphics, its amazing music and the sheer amount of memes it generates... but most of all, by its interesting concept. 

Massive spoilers for a game that's a decade old (!) at this point in time, but Undertale takes the idea of a video game RPG and throws it around its head. We start off with a rather simple concept, with a rather simple system meant to mimic a lot of the oldest Dragon Age and Final Fantasy style games, allowing your protagonist to fight the random encounter monsters. And you are meant to be lulled into a sense of thinking that it's just a mechanic of the game. But as you progress through the game, you realize that everything you took for granted in a video game... experience points, leveling, killing 'random encounters', and most crucially even the act of reloading saves and resetting the game... are all not as it seems. It might seem a bit more quaint now that there's been a fair amount of games that tries to copycat it, but Undertale is one of the first games to effectively make multiple branching routes and endings... where the act of you, the person playing the game, reloading a brand-new playthrough of the game actually affects how the game plays out because the in-universe characters treat it as a time-loop... and some characters will remember that you've been through this before. 

But most of all, what intrigued me the most was the monsters. Because the monsters are actually a huge part of the game. The idea of a 'random encounter', of you walking around a map and fighting an infinite number of monsters that the game generates out of nowhere for the sake of 'grinding' experience points and leveling up, is very heavily deconstructed by this game. 

Again, massive spoilers for a ten-year-old game, but Undertale plays on the concept that each area has a finite amount of monsters. And while you might not realize it early on, the game actually has a mechanic that allows you to play through it without having to kill a single monster. It needs you to pay attention to the world around you, and to spend turns to check and talk to the monsters, but 'battles' in this game also have a way for you to look for alternate actions... to interact with these monsters as you would other people. You can talk to them, intimidate them, flirt with them, try and figure out why they're fighting you... it's like a mini-puzzle in figuring out how to 'Spare' the monster before they kill you. 

I've watched people play through Undertale back when it was super popular in 2015, and it impressed me how funny the game was, but also how well thought-out the game was in terms of making its encounters both tongue-in-cheek but also surprisingly full of heart.

And while I'm not going to spoil the entirety of Undertale, and I don't think I care to review the 'bosses' (who tend to be humanoid characters) I'm going to try my level best to talk about every single monster in the base Undertale game as I experience playing through it for the first time now that enough time's passed for me to purge a lot of the story spoilers from watching people play through the game from my head.
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The Dummy
I would note that a significant portion of the game does revolve around the named characters and bosses, and... and for the most part, I don't think I can review them properly per se. The characters are well-written and the dialogues are witty, and while you do fight a majority of the main characters throughout your playthroughs, I don't think I have much substantial input to say about the visual design or boss fight mechanics of characters like Sans, Papyrus or Undyne. Perhaps in a different, separate post? These couple of pages are just going to mainly deal with the "lesser" enemies. 

Anyway, just like the game's tutoriel tutorial does, we are first introduced to the combat with a Dummy, which... sure is a training dummy, all right! The way that the game's combat functions is that you are presented with a simple 'Fight' attack, and 'Act', which gives you options like checking the enemy, talking to them, flirting with them... and whatever you do, you go through a little 'bullet hell' minigame that Undertale actually does a relatively good job at making it snappy. The game also does a surprisingly good job at introducing variations to this minigame to make the boss fights not monotonous.

Anyway, here's the Dummy, which for all intents and purposes is just meant to be there for you to test out the mechanics. When 'spared', it actually just disappears and flies off. 

Froggit
"Life is difficult for this enemy."
Our first enemy in the 'Ruins' area is the Froggit, a cute portmanteau of 'frog' and 'ribbit'. He's a simple guy, just a cute little frog...  but there's also appears to be something like a second face nestled between his forelegs? I'm never sure what that is. Froggits don't really have much personality, mostly going 'ribbit ribbit'. I do like that in the combat minigame, sometimes instead of little particles flying around, you've got a straight-up pixelated frog jumping around trying to get you. 

Again, massive spoilers for a game that's a decade old now, but while you encounter these monsters in 'random encounters' a la Final Fantasy or Pokemon or Dragon Quest, something sinister happens if you kill too much of them to 'level grind'. Killing a couple might be excusable as you're unfamiliar to the world, but someone who takes the time to level-grind will receive ominous messages like "20 left" and you can literally kill everyone in the area, ultimately leading to "nobody came" and causing the location to feel empty and desolate. 

While there are definitely multiples of each monster, particularly in later areas, the loss of these monsters will be felt down the line, with important characters noting if you've killed certain monsters, and NPCs disappearing as they escape from you when you go down this 'genocide' route. On the other hand, trying to act and talk and just avoid the damage lets you 'Spare' these enemies, still counting as victories and awarding you gold. For Froggit, he's so simple and confused that whether you pick 'complement' or 'threaten', the Froggit will be either flattered or scared enough for you to spare him. 

Whimsun
"This monster is too sensitive to fight..."
Likely to be one of your first non-scripted encounter, Whimsuns are adorable little bug-people. They kind of look like bedsheet ghosts (not to be confused with the actual bedsheet ghost character) with stick-figure arms and legs, and the antennae and wings of a bug. Its expression is very scared. I like his huge eyebrows, his little dot eyes, and what I thought was an upturned mouth is actually a 'snout' with little fangs. Kind of like the Pokemon Venonat. Every line of dialogue he says are something along the lines of "I can't handle this" and "forgive me". Its attacks are programmed to always miss unless you run into them, and this poor little cowardly baby just seems to just kind of...  Whimsun really does need help, doesn't he? I

Whimsuns are programmed to die in a single hit in combat, and whether you 'console' or 'terrorize' him, he's so freaked out that he's going to run away as long as you engage with the non-hostile mechanic. Again, from a game-designer perspective it's important that the early game monsters are able to be spared quite easily, and tying this to the poor Whimsun's neurotic and panicky personalities works quite well.

Moldsmal
"Stereotypical: Curvaceously attractive, but no brains..."
Playing a bit on typical JRPG tropes, one of the earliest enemies is some kind of slime. Moldsmal is shaped like an actual jelly dish, and he blobs in place, making 'burble burble' noises that might lull you into thinking that he is non-sentient. But Moldsmal is still a monster, and all monsters in Undertale are part of a whole race of sentient beings. 

I do like that the options to deal with Moldsmal are quite ridiculous. 'Imitate' causes you to 'lie immobile with Moldsmal', which causes you to understand the world a bit better. You can, however, 'flirt' with Moldsmal, where you both bond and have a 'meaningful conversation' by wiggling.

Loox
"Don't pick on him. Family name: Eyewalker."
Loox is probably the first monster that looks a bit more threatening than everything else that came before, with a fanged mouth and a body shaped like a spherical cyclops. The general look seems to be meant to evoke a more monstrous version of Monster Inc's Mike Wazowski. Pretty simple but neat design -- giant eye, horns, and limbs. 

Again, we are still in the tutorial zone, but Loox is the first monster where your choice of what to do will actually change how the fight goes. With the description and his dialogue rather pointedly showing that Loox doesn't like being stared at, you have the option to 'pick on him' or 'don't pick on him'. The latter lets you spare Loox, but the former would cause his attacks to go a bit more intense. 

Migosp
"It seems evil, but it's just with the wrong crowd..."
A bit of a weirdo, Migosp is a weird little bug-guy with a nervous face and pose. Migosp can only be encountered with other monsters, usually the more aggressive Loox or Moldsmal, and he will join them in attacking you while screaming bug monster lines like "heed the Swarm!" and "Legion! We are Legion!" Again, it's a pretty 'obvious' theme to give a bug monster a hivemind theme, but as the check flavour text notes, Migosp is just in the wrong crowd. A less-literal version of a hivemind, if you will. 

Kill or spare the monster that Migosp shows up in, and he drops all of the creepy hivemind screaming, and actually stops attacking. Instead, during the 'bullet hell' minigame portion of combat, we instead get a little animated sprite of Migosp's little cockroach self just doing a little jig. "La la, just be yourself!" Again, it's a cute little gimmick, and one that helps to give a lot of these monsters a fair bit more personality. 

Vegetoid
"Serving Size: 1 Monster. Not monitored by the USDA."
An interesting monster, you first meet the Vegetoids as overworld items you can interact with as you pull them out of the ground like carrots. And the Vegetoid is basically a monstrous vegetable, in the vein of something like Attack of the Killer Tomatoes. Vegetoid's fight helps to illustrate what Undertale is all about, where all the monsters can only be properly spared if you try to understand what or who their personalities are. Just picking the nice 'talk' options doesn't always work. 

Vegetoid, for his part, responds very negatively to you trying to talk or charm him. "Plants can't talk, dummy." is Vegetoid's answer, and you really need to play by his wacky logic. Instead, Vegetoid wants you to select 'dinner', at which point Vegetoid gets excited and you then need to run into some glowing-green projectiles during the bullet-hell minigame. After having some of its vegetables (or part of itself?) eaten, the Vegetoid can be spared. It's bizarre, but, again, it's what makes this game charming. 

Also, at this point you would fight a couple of plot-relevant characters, but as mentioned above trying to talk about even Toriel or Napstablook would either be a short description, or a super-long analysis on their role in the story and other people have done a much better job of that than I have. 


Ice Cap
"This teen wonders why it isn't named 'Ice Hat."
The second area of the game is Snowdin, a snow-themed mountain. And with a snow-themed mountain, you also get snow-themed monsters... mostly. Ice Cap is a weird little guy with a giant ehad and a tiny body, a carrot nose and a giant fancy hat made up of spikes. Every single line of dialogue he says involves him talking about his hat, boasting about it or mocking that you don't have one, or complaining that you're not looking at his hat.

The attacks in Snowdin has gone a bit more fancy as well instead of just generic projectiles, with Ice Cap summoning pixelated ice stalagmites that launch upwards from cannons that appear from the bottom of the screen. Complimenting Ice Cap just makes his ego bigger and bigger, and the way to spare Ice Cap is to actually ignore him, at which point he gets a bit desperate for your attention, because how dare you ignore his hat and oh god is something wrong with his hat?

As a bit of a cute easter egg, you can try to steal his hat, which fails most of the time... until you've met his sparing conditions. When you do so, Ice Cap... devolves into just an ice cube. Because without the cap, he's just ice. One unique thing is that once you reach a certain part of the story, the Snowdin monsters actually stop appearing as random encounters and show up in the Snowdin monster town as NPCs. 

Snowdrake
"This teen comedian fights to keep a captive audience."
An interesting design. The Snowdrake has a head shaped like a snowflake, while what appears to be the main body of some kind of bird. Kind of an ugly bird, but I think it's just the unnaturalness of seeing those mismatched teeth in the Snowdrake's beak. Snowdrake's whole deal is that he's an aspiring comedian, but he doesn't quite have the confidence to tell his jokes. If he appears with other monsters he gets very self-conscious if you start telling jokes. The way to spare him, obviously, is to laugh at his jokes... but the game wants you to pay attention to what he's saying, and if you laugh when he's not joking, he actually gets mad. 

Snowdrake's jokes, of coures, are very lame Mr. Freeze tier ice puns. Do unrelated actions to his jokes, and Snowdrake will start going "ice puns are snow problem" and the like.

Again, it's dorky as heck, but all Snowdrake wants to do is to tell jokes. It is quite telling that you encounter Snowdrake just as a random encounter, with no real indication that he's a significant character (and in fact, he really doesn't show up in the game like the other important NPCs) but if you actually kill Snowdrake, other characters in town will have their dialogues change. It's at this point when you realize that even the encounters not highlighted by the game as interacting with you in the overworld with copious amounts of dialogue are still living monsters in-game, and they have friends and family.

Chilldrake
"Rebels against everything!! Looking for its friend Snowy."
In fact, this guy only shows up if you kill Snowdrake. Chilldrake is Snowdrake with the eyes replaced by sunglasses. Despite otherwise looking like a simple palette swap -- something common in video games -- Chilldrake is fully different. For the most part he is a simple one-gimmick joke, yelling about simple 'anarchist' stuff, rebelling against doing homework and brushing teeth. He's a cool rebel, y'all, and he'll try to disagree with anything in front of him. His sparing conditions is to actually agree with what he's saying, which makes him uncomfortable because he's suddenly not a rebel anymore. 

But very quickly, you realize that half of Chilldrake's dialogues is him actually looking for his friend Snowy, who has gone missing. He keeps muttering -- particularly if you try joking with him -- that only his friend Snowy gets to do that, and while he's not frantic about it, he's still wondering where his buddy Snowy went. Well, you, dear player, killed Snowy. 

Gyftrot
"Some teens "decorated" it as a prank."
Gyftrot would be a pretty simple reindeer monster, and the joke is that Gyftrot has little Christmas trees sprouting out of his horns. When you encounter Gyftrot he'll have randomly-generated tacky Christmas decorations (and even a dog, sometimes) stuck in his antlers and he's very peeved about it. That alone is a pretty simple monster concept, but I find Gyftrot extra unsettling in all the best ways becuase of its vertically-slitted mouth. Amazing how just a simple change in detail can make a cute reindeer look so unsettling, huh? 

I do really like that the designers thought of extra stuff to do with these monsters. In Gyftrot's case, you need three whole turns to undecorate him... and you can even gift him stuff afterwards to make him feel better. But if you're feeling particularly dickish, you could re-decorate Gyftrot! The reindeer takes this as the utmost level of betrayal, and can no longer be spared in that battle. 

We learn some lore about Gyftrot when we reach Snowdin City, where the monsters' equivalent of Christmas is borne out of a festival made to make Gyftrot feel less bad. Again, like Ice Cap and Snowdrake, at some point after sparing him, Gyftrot will actually show up in town. 

Jerry
"Everyone knows Jerry. Makes attacks 2 seconds longer."
Oh, it's Jerry. Looking like a weird, ugly jellyfish or perhaps the classic stereotypical Japanese maritan, Jerry has a rather wacky expression and doesn't really attack you, he just helps to buff the other monsters that appear with him. Like Migosp, Jerry can only appear alongside other enemies. The little joke, however, is that Jerry is a gigantic dick. A Jerry. Every other possible encounter you could meet in Snowdin will sigh in exasperation if they spawn with Jerry, and every line of description describes him doing something nasty, and when he speaks, he constantly complains or even insults the other monsters. 

In fact, the way to get rid of Jerry is to just pick the 'ditch' option, where you and the other monster that Jerry spawns with just kind of wordlessly agree to ditch Jerry when he looks away, before resuming combat. I thought that was funny. Again, his design is simple but wacky, and his short but memorable role has made Jerry into one of the deserved memes from Undertale. 


Lesser Dog
"Wields a stone dogger made of pomer-granite."
The last four enemies in Snowdin, not counting the spotlight character Papyrus, are all dogs. Cute dogs! They're all technically monsters that you encounter once, but again, I'll be talking about all the 'lesser' enemies. And Lesser Dog is an adorable pomeranian knight in a suit of armour, with a sword and a massive shield. 

And Lesser Dog behaves exactly like a dog, going just (pant pant) and (wag wag) and its attacks involve a simulacrum of a dog bouncing around trying to grab you. The Lesser Dog, like all dogs, is a good dog, and the game gives him like six different options other than the common ones, all of them being 'Pet'. You can technically spare Lesser Dog after petting it just once, at which point it stops pretending to be a knight and just becomes a good doggy, who's a good doggy, yes you, yes youuuu

But keep petting Lesser Dog (because why wouldn't you?) and his neck keeps extending. It has to be seen to be believed, but he just keeps getting more and more and more and more excited. Adorable! Lesser Dog, and indeed the rest of the dog Elite Guards, don't really matter in the rest of your journey, but you'll be able to see him lurking around building his snow-dogs, and hanging out in a bar if you spare him. And if he or any of the other dogs are killed, that will change aspects of a future character's opinion of you. Actually giving us a very very nice and adorable character that just screams 'don't kill the cute puppy', again, is one of the interesting ways that the game tries to make us see these random encounters as people.  

Doggo
"Easily excited by movement. Hobbies include: squirrels."
You encounter the other members of the dog Royal Guard in various checkpoints in Snowdin, the first one being Doggo. Context clues around his site note that Doggo is super bad at detecting a lack of movement, and you can utterly bamboozle his attacks by standing perfectly still and not moving your heart-cursor. It's a tutorial for the 'blue attack' mechanic that bosses will use, but I love that it's delivered in such a in-your-face way, that it's the whole point of this character. 

Doggo can only be spared if you not move, by the way, because once you move, he gets alert and is hyperfocused on taking you down. But if you not move, he thinks there's no one there... and then you can pet Doggo. PET? PAT? POT?

Doggo himself is perhaps my least favourite of the Royal Guard, being a squinty dog-man with two swords and... a rather unprofessional wifebeater shirt. You're a Royal Guardsman, Doggo! Act like it!

Dogamy & Dogaressa 
"This puppy finds her hubby lovely. SMELLS ONLY?" "Husband of Dogaressa. Knows only what he smells."
Next up, we have this pair of dog-people, Dogamy and Dogaressa. They are initially encountered fully hooded, and having the general vibe of executioners. Until battle starts, and it's revealed that they are one of those sickly lovey-dovey couples. Their attacks are all shaped like hearts. Just like Doggo, they can't see movement very well. There's enough context clues in their dialogue to tell you that you need to roll around to smell like a dog, then pet them separately. This blows their mind as they realize that pups "can pet by another pup???" 

If you actually take the brutal way and kill one of the two Dogi, each one has a slightly different reaction. Dogamy becomes utterly distraught and depressed, and his attacks become weak and slow. Dogaressa, meanwhile, gets enraged and her attacks actually become faster. Again, killing none, some or all of the dogs will elicit different dialogue from the survivors, who will all briefly appear in the Snowdin Village. 


Greater Dog
"It's so excited that it thinks fighting is just play."
And our last member of the dog Royal Guard... this this absolute unit. Greater Dog first shows up in the overworld half-covered by snow, seemingly just being the size of a cute little dog. And then it stands up, and turns out he's a big, muscular dog-man with still the adorable head... but exaggeratedly large arms and torso. I love that his spear and bracers also have the cute little dog faces on it. 

Again, the way to spare Greater Dog is a bit more convoluted (similar to the Dogi pair) but the in-game text does make it rather obvious to know whether to beckon him to come, to play, or to pet. Ultimately if you do it right, Greater Dog will actually spend most of his turns just being a cute little sprite-puppy that curls up and wants to play with you. Rather hilariously, after sparing the Greater Dog (of course you have to spare!!!) it turns out that it's actually just a regular sized dog after all, somehow piloting the oversized suit of armour. 
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Anyway... this is probably a nice point to stop, since we're around the middle portion of the game. A lot of the monster design in this game does lean more on character gimmicks and absurd comedy, but it does so in such an earnest and charming way that you can't help but love at least some of them. And we're not even getting into the actual characters like Sans, Papyrus, Undyne and Toriel that take up entire the bulk of the game's dialogue! Which is what makes Undertale interesting, because as lovable as these monsters are to make you want to spare them... the 'Pacifist' route is just one of three, and there is always the option to see what's going to happen. The 'Genocide' route has you kill all the monsters, even the lovable dogs, and you start to see how the world around start to change. NPCs become colder and more curt, and do a complete genocide and the game world will actually permanently scarred even if you uninstall the game. Undertale's huge gimmick about monsters being people isn't new, with friendly orcs and slimes being around since forever... but it's also one that tries to deconstruct the idea of random encounters, and infinite supplies of faceless enemies that die needlessly. I don't think this is so much of me 'reviewing' these monster designs but more of an appreciation/reaction post. 

Saturday, 9 May 2026

Reviewing 5E D&D Monsters - Mordenkainen's Tome of Foes, Pt 3 (Devils and Yugoloths)

Standard
Mordenkainen's Tome of Foes introduced almost a dozen new Demons, and a bunch of Demon Lords. In contrast, it gave us a fair bit fewer Devils (and Archdevils)... but that has always been the case for the Demon/Devil dynamic throughout D&D, where the Demons, being far more variable and mutable, always receive more variations. In contrast, the regimented, rank-based structure of the Nine Hells does make it a bit hard for the designers to add a Devil; particularly to justify why that ranking hasn't been previously filled in before. 

So we only get around 6-7 new Devils (I'm not counting the Abishai separately). But the Yugoloths get a lot more representation in this book after being a bit of an afterthought in the original Monster Manual. It's still not a whole ton of expansion, but between the new Yugoloth species here and the writeup in the lore segment of Tome of Foes, it is a much-needed and much-welcome addition to the Yugoloth and the direction 5th Edition is taking towards them being mercenaries and manipulators. 

Tome of Foes stats out six Archdevils, but none of them are particularly interesting to talk about visually except for snake-bat-man Geryon, since they are all variations of the 'horned, bat-winged devil-man' trope. Which is nice, I suppose, since the devils always felt a bit more visually cohesive compared to the demons, but it also really doesn't leave me much to talk about without discussing infernal politics and variations in spell lists. So yeah, even moreso than the demon lords, I don't have much to say about the archdevils. 

And the poor, poor Yugoloths, don't even get a 'named' general or unique big boss. 5E only mentions the 'General of Gehenna', who doesn't even have an art piece. Poor, poor Yugs! At some point, someone will appreciate you guys.  
  • Click here for the previous part.
  • Click here for the final part.
  • Click here for the index.
[Originally published in June 2020; revised in May 2026]
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Red Abishai
Devil - Abishai
  • 5.5E/5E: Medium Fiend - Devil; Lawful Evil; CR 7 (Black), 17 (Blue), 15 (Green), 19 (Red), 6 (White)
In designing the Devil hierarchy, the designers made it quite difficult to introduce new variations without explaining why, for example, there's a sudden new rank or stage between, say, the Chain Devil and the Bone Devil. With how rigid the diabolic structure was presented in 5th Edition, it was a bit interesting to see how the 5E team tried to side-step adding new ranks (and really, it could very easily be 'alternate forms' of the same rank). One of the ways they did this was to add devils that are technically Baatezu Devils, but are so specialized or weird that they stand outside the hierarchy. 

Enter the Abishai. The Abishai are devil-minions of Tiamat, the God-Queen of evil chromatic dragonkind. Tiamat technically is a lawful evil creature that lairs in the Nine Hells, but she's more like a VIP tenant instead of part of the management. And as a VIP tenant, Tiamat gets to make some hiring decisions for her own personal staff. 

Mortals who won Tiamat's favour before death end up being bound to her, transformed into an Abishai. Abishai are... basically just Dragonborn with wings and some dreadlocks. They're naked, too. Visually, they are kind of diluted compared to so many other draconic-adjacent creatures in D&D, so I don't really find them special. And just like the Mephits in the Monster Manual, the Abishai takes up a fair amount of space, with all five chromatic colours getting a dedicated stat block and artwork. Unlike the Mephits, there's an actual gameplay usage here, because the Abishai aren't clustered around the same rough CR. No, the White and Black Abishai are a rather weak CR 6 and 7 respectively, whereas Green, Blue and Red go from a CR 15, 17 to a whopping 19. In context, Balors also have a CR 19!

White AbishaiBlack Abishai
And I find the fact that these dragon-man devils being as powerful as the Balors and Pit Fiends to be a bit... underwhelming. They're just dragon-man minions of Tiamat. I really feel like at least the Red Abishai should have been a bit more dramatic visually, surely? It doesn't help that the original incarnations of the Abishai in 2E were actually identified as lesser Baatezu, noted to be gargoyle-like and being the fodder of the Nine Hells.

My underwhelmed reaction to the visuals of the Abishai aside, the Abishai themselves work okay as Tiamat's personal minions. They represent her interests all throughout the planes as her heralds, and also serve to lead armies or assassinate targets as needed. They stand outside the hierarchy of the Nine Hells, but by technicality Asmodeus can command them. Other devils shy from interacting with Abishais because they never know whether it is an Abishai working under Tiamat's orders or Asmodeus's. 

Going from the weakest to the strongest, the White Abishai act as simple scrappers, fighting without fear and being crazy whirlwinds of destruction on the battlefield. Their statblock isn't anything special, just a bunch of melee attacks with the addition of devilish traits like magic resistance. Black Abishai are assassins and infiltrators, and have the ability to cast the Darkness spell innately, allowing them to creep and assassinate targets. Oh, all Abishai have the element of their respective dragon in their bite attacks, although the mortals that become the Abishai doesn't really have anything to do with the coloured dragons. 

Green AbishaiBlue Abishai
Jumping up in the power level is the Green Abishai, the first one to have spells. Just like Green Dragons, Green Abishai have a bunch of domination, charm and illusion spells. Green Abishai work as diplomats and intelligence agents, using their charm to negotiate and manipulate opponents, while also digging information. 

Blue Abishai, just like Blue Dragons, are the smartest with the widest amount of spells, going up to level 7 spells. They work as seekers of forgotten lore and lost relics, spending most of their time researching occult grimoires and improving their magical abilities to increase their skill at spellcasting. 

3e1e
And finally, Red Abishai are the ultimate in raw power amongst the Abishai, being a mighty hand-to-hand combatant, and being able to incite a fanaticism buff on its minions, unleash a frightful aura, and channel Tiamat's power through 'Power of the Dragon Queen', which allows a Red Abishai to command and control a dragon. Chromatics are more susceptible to this, but other than some exceptions, most Chromatic Dragons would already obey Tiamat. But Red Abishais can theoretically dominate a Metallic or Gem Dragon this way. I do like the sheer power difference as something that could be a 'gotcha', and from a power level standpoint I do appreciate Tiamat having some stronger minions. 

And ultimately... eh. 5th Edition seem to really like using the Abishai, and I keep seeing the stat blocks appear in so many random adventures. I suppose being always-evil humanoid-sized dragons technically does make them a nice villain to toss into an adventure and allow them to carry the 'Dungeons' part of Dungeons & Dragons? They're all right, for what they are.
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5e

Devil - Amnizu
  • 5.5E/5E: Medium Fiend - Devil; Chaotic Evil; CR 18
A mere medium-level devil in all older material, the Amnizu gets a gigantic buff from being middle management to basically being essentially department heads, just below the C-Suite. They go from being unmemorable 'gate guards' in older editions most known to act as the diabolic equivalents of the TSA into being overseers of lesser demons. Which, I suppose, from the gap between their nothingburger appearance in 3E to 5E, I guess they really performed well? I know it's not a direct contrast, but the Amnizu make a leap from a CR 7 devil in 3.5E to a CR 18 in 5E; eclipsed, I believe, only by the Pit Fiend and Red Abishai among the common demons. 

Amnizus in 5E now lead infernal legions into battle in addition to overseeing the gateways to hell. They are now highly intelligent tacticians, arrogant and ruthless, and I guess the role of guarding the new souls that flow from River Styx into the Nine Hells has became much more vitally appreciated by devilish management over the years. They are also noted to be the ones responsible of indoctrinating the Lemures entering hell, so they also handle orientation of new hires. I guess that's why the Amnizu got such a meteoric rise in the megacorporation metaphor that is D&D's Nine Hells; they are really good at multi-tasking. 

3e2e1e
5E has its Amnizu still technically have the 'pig head and pug face' of its previous descriptions, which actually looks quite gloriously grotesque the longer you stare at the artwork. The Amnizu dresses in regal robes like a bureaucrat would be, and two stunted wings pop up from its shoulders. It really looks kind of like a Hutt from Star Wars, don't you think? 

At CR 18, Amnizus are mighty spellcasters, which match their role as bureaucrats and leaders. They have various spells like Dominate Monster, Command, Charm Person and Feeblemind to control or break the minds of those that dare fight it, as well as Fireball in its spell list for good reason. It can innately poison the minds of those around it, as well as inflict short-term amnesia. And perhaps the deadliest part of the Amnizu's kit is its 'instinctive charm', which forces a save from any creature that attacks it, and if they fail, they will instead attack one of their allies. 

This was a devil that I didn't think much of during my first run through this book, finding the 'HR demon' funny and a cute twist, but didn't otherwise mention much else about the Amnizu. I do appreciate it a lot more now, particularly its power level. The fact that the Amnizu is so strong does speak to the fact that the Nine Hells really does run itself like a bureaucracy for better or for worse. 
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Hellfire Engine 
  • 5.5E/5E: Huge Construct; Lawful Evil; CR 16
The Hellfire Engine is classified under 'devils' in the original printing of Mordenkainen's Tome of Foes, but is technically a construct created by devils. Between Warcraft III and Warhammer 40K, though, I am all for the forces of hell creating impractical ballistae and catapults empowered by hellfire with grotesque features that are handwaved by 'hell magic powers it'. And that's what this particular Hellfire Engine is like, with four roller wheels, a giant screaming face with a cannon-furnace-mouth; two smaller mismatched faces with screaming cannon-furnace-mouths of their own; and tiny little claw fingers. 

And this is, of course, just a potential version of the Hellfire Engine. It is described as having 'many forms, one purpose. One of its abilities is the 'Flesh-Crushing Stride', so it could technically be a mecha like the Fel Reavers of World of Warcraft fame. The Hellfire Engines aren't just mindless constructs, though. They are 'semiautonomous', albeit with an intelligence of merely 2. Why are they semiautonomous, you ask? They are powered by souls. Because of course they are powered by souls. It's hell, after all!

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Hellfire Engines are normally held in reserve unless demons or particularly powerful adventurers reach the gates of the Nine Hells, but occasionally one of these diabolic machines gets loose, and just rampages with its need to destroy. Hellfire Engines just go around to kill as many things as it can, and the souls killed by the Hellfire Engine will transform the creature's soul into a Lemure, unless really powerful resurrection magic is done within a short amount of time. This effect does not extend to demons, unfortunately, which would otherwise really turn the Blood War's balance. 

In addition to that effect that turns all that it kills into Lemures, the Hellfire Engine also has several possible ammunition that it can shoot out. The 'Bonemelt Sprayer' unleashes acidic flame, the 'Lightning Flail' launches an electricity-charged bludgeon, and the 'Thunder Cannon' just launches a massive sonic boom. Presumably, each face in that 5E incarnation has its own hellish rounds.

It does lead me to wonder why the Devils don't just send out these Hellfire Engines to harvest souls from the mortal world, since this seems to easily bypass the 'turn a mortal's immortal soul into a devil by deals and pacts', but maybe there's something that really limits the production or effectiveness of the Hellfire Engine? Other than that nagging question, I do like this cool hell-machine, and of course it's the devils that would be organized enough to create proper artillery devices and keep them in reserve. 
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Merregon
Devil - Merregon / Legion Devil 
  • 5.5E/5E: Medium Fiend - Devil; Lawful Evil; CR 4
The Barbazu and Hamatula are all right 'minions' for the Devils, but there's always something a bit too... barbaric or beastly about them that doesn't feel quite right for the lawful-evil mega-corporation-meets-army vibe of D&D's Nine Hells. Tome of Foes introduces another lower-ranking devil, the Merregon, who are simply orderly soldiers with melee attacks, some devilish resistances, and the ability to jump in front of an attack meant for its master. The 'Blood War' section of the book identifies Merregons as being ranked similarly to Bearded Devils. 

Merregons debuted in 3E as a very different creature, a simple devil-man with yellow skin and horns. The idea was still to give the devils a very soldierly/knightly army minion that looks visually a fair bit more disciplined than the berserker-looking Barbazu, and the very beastly Spinagons and Hamatulas. That is probably why with a bit of an armour redesign, the Merregon shows up as one of the minion devils in Baldur's Gate III.

5E then took the Merregon and completely redesigned it, instead giving us a very simple looking design. A muscular purple-skinned soldier with golden armour and a red cloak. Normally I am against making a creature, let alone a fiend, become even more humanoid... but in this case, everything around the Merregon's vibe is compressed to just one feature -- its mask. Its golden mask, depicted with an almost baby-like sculpt to it. The Merregon legion has no need for identities or individuality, and therefore are reduced to identical masks. The masks can be different, and each Merregon legion has its commander and hell layer stamped onto it. 

Before you feel bad, the Merregon are created from the souls of "fallen soldiers, mercenaries and bodyguards who served evil without reservation", so the assholes who just go around committing atrocities with the justification of them 'just following orders', and get dragged down to the Nine Hells alongside their masters and get transformed into Merregons. Their masters at least would have the balls to plan out and have a greater goal. These would-be Merregons are just there, 'following orders' and using that as a justification to dodge judgement and accountability. And with this, they have an unshakable loyalty (whether willing or not), forming near-suicidal robotic minions that will serve their masters. 

Not exactly explained in the flavour text, but it seems to be definitely implied that there's something 'less' about the Merregon that will prevent it from ascending or evolving into a greater Devil, unlike even the lowliest Imp, and these legionnaires will serve eternity as unthinking, unfeeling minions. 
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 Narzugon
Devil - Narzugon / Hell Knights 
  • 5.5E/5E: Medium Fiend - Devil; Lawful Evil; CR 13
Undoubtedly inspired visually and name-wise by the Nazgul of Lord of the Rings fame, the Narzugon are a pretty simple concept. A bunch of knights in spiky black armour, riding fiery Nightmares. They don't quite look as creepy as the Nazgul's empty robes, and while I get that D&D can't just blatantly plagiarize the Nazgul look, I really felt like they could've done something to make the Narzugon's appearance stand out a bit more. Surely some horns or wings couldn't hurt? 

The CR 13 Narzugon has a pretty neat backstory, essentially a diabolic, undead version of a Blackguard. They are Paladins who made deals with Devils, and in an interesting mix of 'lawful', end up carrying their twisted sense of honour into the afterlife. It's another way to get a Devil that's uniquely 'outside' the normal hierarchy, due to the rather specific origin. Narzugons are thus unquestioning champions that lead legions of the Nine Hells in war, carrying out the will of their masters. 

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Narzugons are able to use their 'infernal tack' to summon their Nightmares at any time. They also have hellfire lances, and anyone slain by these lances also get turned into a Lemure, similarly to the Hellfire Engine's effect. That's... again, that seems to bypass a lot of the trouble that devilkind goes through to make new devils, so there probably should be some justification why Narzugons and Hellfire Engines aren't just deployed en masse to harvest new minions.

In addition to the Hellfire Lance and the ability to summon a Nightmare steed, Narzugons are able to unleash 'command' auras for its minions, and most interestingly, as a leftover of its time as a living paladin, able to heal an ally -- a rarity among fiends. Narzugons are ranked quite highly in 5th Edition, being ranked alongside Gelugons in Tome of Foes, although they were relatively lesser devils in older editions. They're pretty cool inherently, but I otherwise don't have much to say about them.
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5e
Devil - Nupperibo 
  • 5.5E/5E: Medium Fiend - Devil; Lawful Evil; CR 1/2
Sometimes, the souls that get sucked into the Nine Hells don't get turned into the Lemure. Sometimes, you are so much of a loser that even when the devils looked at your soul, they decided that it sucks so badly. And you become a Nupperibo devil instead. Souls whose evil acts arose from 'carelessness and sloth' get turned into these grotesque, bulbous beings that are walking globs of fat and tumorous flesh, with sewed-up mouths and eyes, and a constant mass of buzzing insects rising from their bodies. Truly a nasty corpulent 'monstrously fat' creature, and one that's a lot more monstrous than its previous incarnations (who are 'just' regular fat people). The Nupperibo truly looks pitiful and wretched. Mordenkainen describes the Nupperibo as beings without ambition, who simply cannot have rise in the treacherous hierarchy of hell, instead stepping down, becoming even lesser than the Lemure. 

The Nupperibo shuffle mindlessly across the Nine Hells. Blind, bloated, eternally hungry, and just groping around for whatever vermin or filth they can scoop into their mouths. Nupperibos are noted to be completely pathetic, and at a CR of 1/2, they have no real interesting statline to speak of to really fight. But they are noted to gather around in throngs, and in enough numbers, can clog up a vital passage or even an entire valley. Devils send telepathic messages to the Nupperibo and they are noted to be delightfully easy to command, but no devil really wants to use Nupperibos unless they are forced to, since their presence does nothing for the generals' status. 

A Nupperibo's cloud of stinging insects torment any non-devil around them, and in a rather interesting addition, a Nupperibo's swarm of insects appear to 'latch' onto whoever they attack, and a Nupperibo can flawlessly track anyone that the insects have stung in the last 24 hours. It's a surprisingly useful ability, if only the Nupperibo isn't so utterly despised by other devilkind.

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Hilariously, the Nupperibo's artwork is very weirdly censored in the reprint to Monsters of the Multiverse, which covers up the bottom right side of the artwork with a huge text box. It's rather awkwardly done, and I guess the point is to cover the Nupperibo's... crotch? Which doesn't have anything resembling naughty bits of anatomy? If there's some part of this artwork that's objectionable, wouldn't they just commission new art or something? Odd. 

Also, the Nupperibo draws its name, rather bizarrely, from a Japanese yokai more commonly parsed as 'Noppera-bō', who resembles a faceless human with no face. There's absolutely no commonality between D&D's Nupperibo and the mythological inspiration, which really just feels weird. 
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Orthon
Devil - Orthon 
  • 5.5E/5E: Large Fiend - Devil; Lawful Evil; CR 10
Mmm, not feeling this one. The Orthon of older editions just looked like bulkier orcs, and that's boring, sure. But 5th Edition's redesign makes it... a skull-faced ogre with big tusks? That doesn't really scream 'devil' to me, and the rather awkward pose doesn't help, either. The Orthon is described as basically a bounty-hunter of the Nine Hells, being hired like a hitman by greater devils to hunt down, track and either capture or assassinate a certain target. It's... it's an all right concept, I guess, to justify a 'specialized' devil that sits outside the hierarchy. It's even a neat concept of having 'a devil that hunts devils', giving potential inter-fiend political drama. 

It's just that there really is not much about the Orthon beyond that. The flavour text highlights its abilities, sure -- super-sharp senses, the creation of an invisibility field, six different Green-Arrow-style trick arrows, and it detonates to wipe out all evidence and equipment when it dies. The Orthon's personality and tactics is reduced to it being a professional that sometimes indulges in the chase and one-on-one combat. Maybe you can hire them as a guide. It all seems quite basic.

This has nothing to do with older editions of Orthons, who were pain-wracked yet professional soldiers in 3E, and 'Rage Devils' in 4E that are simple brutish berserkers. So at least 5E Orthon had something unique going for it. 

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Visuals aren't everything, but it really does make me not get excited to talk about the Orthon compared to all the other fiends on this page. And the concept isn't bad, but the flavour text builds up so little of it and raises even more questions than anything about how bounty hunting in the Nine Hells even work. How do other non-Archduke devils view the Orthons? How are their contracts different? Do the Orthons have some loophole that incentivises the Archdukes to hire them instead of one of their regular minions? The more I think of it, the more the new flavour of the Orthon actually fits the mercenary nature of the Yugoloth instead of the Devils. 

As one last note, an Orthon actually appears in Baldur's Gate III, which is a game I need to play and probably will have their redesigns reviewed separately when I get to it. Their take on the Orthon is still essentially a big ogre-devil man, but the pose and the accessories really makes their version of the Orthon a lot more menacing and selling of a Predator-meets-Boba-Fett style character. 
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Yugoloth - Canoloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 8
We're going in to the Yugoloths introduced in Tome of Foes, now, and after only getting a mere four in the Monster Manual. So while Tome of Foes doesn't give us as many Yugoloths as Devils and Demons, we do get a fair bit of expansion for our favourite contractor mercenary Daemons. 

I keep misremembering this guy's name as the Carnoloth, as in carnage. It's the Canoloth, though. Unlike most Yugoloths, the Canoloth is more of a dog-like creature, essentially being an armoured bulldog with a face comprised entirely of a fleshy maw. No eyes, just a round maw filled with a sharp teeth and a barbed tongue that extends out of it. It's a pretty cool monster design! I like it. Canoloths are essentially acting as contracted guard dogs, guard exactly what they are contracted to guard, and nothing more and nothing less. It's almost like an 'opt-in' service, because Canoloths won't kill or pursue, and merely subdue the interlopers unless contracted to. 

Canoloth and Ultroloth - Wayne Reynolds3e 
2e
Canoloths have 'uncanny senses' that allow them to pinpoint invisible creatures, and even have an ability called 'Dimensional Lock' that prevents teleportation around it, so they are absolutely detecting and stopping anyone from teleporting near the item or person they are asked to guard. However, at a mere CR 8, the Canoloth isn't the fiercest creature out there, and so it might probably need to be supported by stronger Yugoloths to properly defeat thieves. Especially if the thieves happen to be appropriately-leveled adventurers.

A pretty cool 'daemon-dog' monster design for sure, but as we go on down the Yugoloth list in Tome of Foes, you'll see, really, the lack of identity for the D&D Yugoloths compared to D&D's demons (a lot of them are animalistic abominations) and devils (most have traits of the classical Satan features). To recap, Monster Manual gave us a fox-man, a gray alien, a bug-man and a gargoyle devil-man... and tossing in an eyeless dog, another bug-man, a frog-man, a devil-man with a huge arm, a diseased goat-man and Charon is really not giving the Yugoloths a particularly nice or mercenary-themed visual identity. Bit of a shame, that. 
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Dhergoloth
Yugoloth - Dhergoloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 7
I really like the Dhergoloth. They are so weird-looking, especially compared to their fellow lower-ranked bug Yugoloths, the Mezzoloths. Mezzoloths are just... bug dudes. Dhergoloths have a bizarre, radially-symmetrical body plan. Three legs, five arms, arranged around a hard cylindrical body, and the head of a monster ant in the center of it. It's so much weirder than just the Mezzoloth, where you could be forgiven into thinking that they're merely 'just' bug-people like the Thri-kreen. 

The Dhergoloth is described as a 'whirlwind of destruction', probably because of the arrangement of its arms. As Mordenkainen describes in this book, their head, torso and waist all spin around independently of each other like a toy. That's fun! This is depicted in-game as a frantic movement-plus-attack. While mostly a melee warrior, Dhergoloths are also capable of teleporting, and casting the Yugoloth staple spells of Darkness, Fear and Sleep. 

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Dhergoloths are simple, dumb brutes, happy to take contracts that lead them towards causing as much death, butchery and mayhem as possible. Their stupidity makes it so that they can really only take simple orders, otherwise they will forget what they're supposed to do in the midst of the action and really bungle up the task set for them. They don't really mention it in the writeup, but I imagine that they might be the 'discount bin' Yugoloths. Instead of getting the professional soldiers like Mezzoloths and Nycaloths, someone who tries to bargain too much might be given some Dhergoloths instead for a cheaper price. 

A huge fan of the Dhergoloth's various iterations, too. 2E had a huge ball with very slender arms. 3E has the same layout of limbs, but by making the body fleshy and not buggy, it looks so weird and lumpy. Not a bad design! 4E goes for a more menacing 'scarab man', and while it still has five hands, the fact that the head doesn't pop up of a cylindrical body does make the 4E Dhergoloth (well, Derghodemon) lose some of its uniqueness. 

Very fun design. Almost made me wish that all the lower-ranked Yugoloths had a demon-bug theme just to be somewhat consistent, and moving into humanoid or daemonic forms as we go up the hierarchy, but alas. 
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5e
Yugoloth - Hydroloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 9
We get another 'frog man', which, by this point in 5th Edition's publication, is the fifth frog-person of some sort after the Slaad, Bullywug, Hezrou and Grung. Sixth if you count the Froghemoth. I get that many of these are iconic from D&D's history, but when selecting from which of the numerous fiends from D&D's history to adapt, I was surprised that they went with the Hydroloth... and really did nothing to make it look anymore fiendish than just a particularly monstrous frog-man. It's got a bumpier hunchback, and skin-flaps a la sugar gliders that isn't the most clear from the art. 

Hydroloths inhabit the River Styx, which in D&D cosmology drains the memories of souls in the afterlife, and aren't the only Yugoloth in Tome of Foes who does this. So I guess the idea is to have the Hydroloth and Merrenoloth before be part of the same campaign? Other than being an otherwise basic water enemy with the fiendish resistances, the Hydroloth has a bunch of water-themed and memory-themed spells. The whole idea is that the Hydroloth is immune to the waters of the River Styx, and can steal memories from those around it. That last bit, memory-stealing, is probably the most interesting thing about the Hydroloth! Really wished they leaned more into it for its abilities, like perhaps it could temporarily 'steal' spells from your characters or something. 

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Tome of  Foes gives several potential plot points not tied to the River Styx, which is a very setting-specific aspect. In addition to stealing memory, Hydroloths are experts at 'finding lost things', particularly those swallowed up by the depths. They are also the most powerful Yugoloths in underwater conflicts, and sometimes hire themselves out. Okay.

Again, I am... not the most impressed, either visually or thematically. Was it that necessary to bring in the 'aquatic variant' so early on in publication history? I wonder if there truly was that much demand for aquatic fiends, and even in maritime adventures like Ghosts of Saltmarsh or Call of the Netherdeep, the underwater threats tend to not be fiendish in nature. (And I'd rather they have adapted the far cooler Piscoloth instead of the Hydroloth for an aquatic yugoloth...) I don't know. Maybe if there's something more about the Hydroloth, maybe some more aspects about its memory-stealing that's highlighted somewhat, would have made it a bit more interesting. 
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5e

Yugoloth - Merrenoloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 3
At a mere CR 3, the unassuming Merrenoloth is actually quite a bit of an interesting creature in that it has lair actions and regional effects, things that are usually reserved for truly powerful monsters. I feel like you can justify having so much specifics when you actually do go all-in. I may not like that as much, but I can respect that. Merrenoloths are visually and conceptually based on the boatman of the underworld, Charon, from Greek mythology. Its design is very simple, just a skull-faced boatman on with an oar on a boat. In their original debut in 1st Edition's Monster Manual II, they were even called the very blatant 'Charonadaemon'.

Merrenoloths have complete and utter control of their vessels, with the intention of ensuring that their passengers reach their destinations safely. Transporting someone, after all, can be considered a mercenary contract as well. In addition to crewing their ships across the waterways of River Styx, Merrenoloths can also be hired to captain other vessels, and they can afford those ships the same protection, essentially turning ships into their 'lairs'.

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Merrenoloths will bond with their ships, and in their contracts, they most often want a stipulation that they are in no obligation to fight or battle, but merely to its vessel. I think there is also a bit of a sinister loophole where the Merrenoloth doesn't also care about the crew, just the vessel. On their own ship, Merrenoloths can supernaturally navigate the ship through the worst storms, repair the ship, and cause winds to either blow the ship onwards or to make the deck of the ship into difficult terrain. The mere presence of the Merrenoloth causes ships to not sink even when struck with holes, never strays from the direction the Merrenoloth directs it towards, and people on board don't get seasick. 

Again, there is a lot of power and specificity here, and the fact that the powers I've described so far are all only minimally combative means there's still a lot of leeway for the DM's to give the Merrenoloth fancy powers for. I really do wish more Fiends and Fey get to play with so much more specific aspects instead of just cherry-picking from the spell list. Merrenoloths don't like combat, but if forced to defend themselves (probably by someone who really wants to sink the ship), they have a fear gaze, some weather-themed spells, and the ability to teleport. Oh, and to whack you with its oar, which is classified as a magical weapon. 

The Merrenoloth more than any other fiend in the 5th Edition incarnation of the game seems built to be an NPC of sorts, either one that the adventurers need to work alongside, or a priority target that is protecting adversaries on an unstoppable boat. I really do like this guy a fair bit.
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5e

Yugoloth - Oinoloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 12
Oooh, look at that nasty face. The Oinoloth is a rather typical 'goat-headed demon' similar to the Bulezau, but instead of looking imposing and terrifying, the Oinoloth is truly ridden with pustules, cysts, and the artist did a particularly good job depicting his disease-wracked face. Oinoloths are a middle-ranked Yugoloth with a huge theme of pestilence. Previous editions actually have Oinoloth as a rank, as 'Anthraxus, The Oinoloth' was described as one of the more powerful Yugoloths. For a faction that doesn't really have many 'archfiends', it is a bit of a shame that they get reduced into a mere 'type' of Yugoloth. 

Oinoloths are described as 'grim specters of death', and armies have broken down and fled at the sight and knowledge of an Oinoloth. They are described as 'ultimate solutions to thorny problems'... and that solution, well, simply means mass murder of everyone involved. Oinoloths are hired only as a last resort, being launched at armies as chemical warfare, launching and poisoning the ground and creatures they encounter. 

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Tome of Foes also describes the Oinoloths sometimes being hired to lift the very plagues they spread. But being fiends of pestilence, Oinoloths charge a particularly high price for that. Which is good -- if unethical -- business, I suppose. But this cure comes with a typical fiendish twist, turning the creatures they save into debilitated wrecks. 

The Oinoloth has a pretty fun statblock, with its primary ability being "Bringer of Plagues", where it blights an area around itself, and causing all plants around it to wither and all healing to be halved. They are also afflicted with a special kind of necrotic poison that has the chance to cause them to not be able to be healed at all. In Tome of Foes, this necrotic damage will actually damage all of the Oinoloth's allies (and some might argue, the Oinoloth himself) but Monsters of the Multiverse revised this to have the Oinoloth now deal poison damage instead of necrotic damage, which all Yugoloths are immune to. 

In addition to Bringer of Plagues, the Oinoloth has a mass of spells under its belt (Globe of Invulnerability, Wall of Fire, Feeblemind, Invisibility), teleportation, a transfixing gaze, and my favourite -- 'Corrupted Healing', which is a nice nod to the flavour text. Corrupted Healing will heal whoever the Oinoloth is hired to heal, but will inflict exhaustion and a permanent reduction in hit points! I particularly like this, and especially if the DM flavours the plagues spread by the Oinoloth as only being able to be cured with the Oinoloth's knowledge. 
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5e
Yugoloth - Yagnoloth 
  • 5.5E/5E: Medium Fiend - Yugoloth; Neutral Evil; CR 11
I can't take this guy seriously. Look at that artwork! The Yagnoloth is a huge red-skinned devil-man with bat-wings for ears, and a mismatched set of arms. One being a tiny, scrawny human arm and the other being a big, muscular daemonic arm. The concept of the Yagnoloth is that it represents the duality of making deals with fiends, with the 'human arm' being there to shake hands for a deal, and the 'daemon arm' being there to break your bones if you renege on a deal. They cover one arm with the cape, depending on the stage of the contracting process. Conceptually, I get it. But visually, it really is hard to look at this thing and not think of the 'wanking arm' joke. 

The CR 11 Yagnoloth is apparently the being that most beings that would contract Yugoloths deal with, so they are like, dispatchers or receptionists or something. It's an interesting system, which is interesting. Do Yagnoloths always appear in front of any cultist who tries to summon a Yugoloth, and coordinate the contracts and fees even if they're summoning lowly Dhergoloths and Mezzoloths? The Tome of Foes doesn't say, so that's a whole lot of interesting dynamic that the DM would have to figure out. Yagnoloths follow the dictates in the contract it has negotiated, but Yugoloths are not as bound to contracts as Devils are, and Yagnoloths are certain to include loopholes to escape its obligation if needed be

Yagnoloths are in an interesting position. The Yugoloth hierarchy isn't quite as rigid as Devils, but Yagnoloths are still a mere CR 11, right smack-dab in the middle of the Yugoloth power level rankings. However, due to their unique function, they only take orders from Arcanaloths and Ultroloths -- meaning that they, on paper, have full authority and expect obedience from all the other fiends under their command. I imagine this would cause some friction between other ambitious Yugoloths, which would be a bit fun. 

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Yagnoloths probably don't like to join combat, being that they excel as contract negotiators, but when they do, a Yagnoloth will throw off its cape to reveal 'its brutally powerful giant appendage'. Actual quote from Tome of Foes, which is sadly censored in Monsters of the Multiverse. Yagnoloths are bizarrely associated with lightning spells, having an Electrified Touch attack, and Lightning Bolt in its spell repertoire. It can also drain life from enemies, and allied Yugoloths around the Yagnoloth can get bonuses with its leadership cunning. 

Again, the Yagnoloth is a bit too weird, and I almost wished that we had gotten one ofthe more monstrous head designs from previous editions. But again... I do feel like this does fall a bit into a lot of the Yugoloths' confused identity, with a lot of the 'this feels like an evil mega corporation' vibe and all of the contract themes already being done by the Devils. It really does make the Yugoloths feel like something that 5th Edition are obligated to include due to their relative popularity among the fandom as one of the major fiend factions, but they don't actually know what to do with the Yugoloths as a faction other than adapting them wholesale from older editions.