Way of the Long Death Monk Subclass Guide

As promised in our guide on the Monk Class, there are loads of ways to play and portray your martial artist.

In this guide, we will discuss how to make Way of the Long Death Monk. In earlier editions of D&D, this type of monk was often associated with different types of cults, usually oriented around some type of advanced undead or necromancy.

In 1st, 2nd, and 3rd edition, monks got an ability called Death Touch, which was inspired by the old kung fu film trope of the poison hand, the five-finger death punch, or the buddha palm.

This subclass took that idea and made a whole class option surrounding this monk’s fascination with the perfection of self to the point of immortality while also being able to summon death with a single strike.

What Is a Way of the Long Death Monk?

A Way of the Long Death Monk is a subclass originating in the Faerun setting of the Sword Coast Adventurer’s Guide that creates a martial option with flavor similar to a grave cleric or necromancer wizard.

Though all monks are familiar with violence, the Long Death Monk is a specialist in studying that moment right at death. They hold death reverentially and seek to understand what happens right at the transition from life to death.

In this way, they lose all fear of death and even gain bonuses every time they judo-toss a creature through the veil.

All monks gain abilities that make them more and more impervious to death and old age. The Way of the Long Death Monks are those who are fascinated with that process of physical perfection so that when their time to crossover comes, they can do so as seamlessly as possible.

In this post, we will first discuss the mechanics of the Long Death Monk, what is great about them, and what they are lacking so that you can make the early decisions around how to play one.

After that, we will go into actually building your Way of the Long Death Monk: what to consider in your back story, which races, stats, skills, feats, etc. — everything you’ll need to consider with this fascinating subclass.

The Long Death Monk’s Defining Attributes

  • Death touch
  • Cause fear
  • Nearly immortal

Death Touch

The first ability a Way of the Long Death Monk receives is similar to The Fiend Warlock’s first-tier ability. By reducing an enemy to 0 Hit Points (while in melee), you gain temporary hit points equal to your Wisdom modifier + your monk level.

This means you can be in melee for longer than your average monk without spending all of your ki points on dodging incoming attacks, thus freeing up your ki points to use flurry of blows. More attacks equal more downed monsters, which equal more temporary HP. Win-win!

That boost to HP might not seem like much, but it is nearly constant. So long as you keep dropping the minions, you can stay in the fight without dominating the healer’s time and attention.

At 17th level, your death touch improves in a staggering way. You can now spend up to 10 ki points to add 1d10 necrotic damage to your unarmed attack. This damage is subject to a Constitution save, but the save is only for half damage!

This is where your death touch becomes the stuff of kung fu legend. Like Jet Li, you can explode the heart with a single punch. Like Beatrice, you can pinch off the valves of the heart and kill your enemy in five steps.

You carry death in your palm.

Cause Fear

You gain the ability at 6th level to cause your enemies to be frightened with an action. This action costs nothing – no ki points, no spell slots, no per-rest recharge. You can just use an action to scare the life out of every creature in 30 feet.

This might seem a bit random at first, but in truth, you are inspiring the fear of death in your enemies. From a mechanical perspective, this ability benefits you indirectly.

Since you will definitely be in melee, those who are frightened by you will have disadvantage on attacks against you. Furthermore, since they can not move closer to you on their own terms, you will be deciding which enemy to engage and how.

With this ability, you can now prioritize your attacks and your actions so that you can be more strategic about gaining the temporary HP from your death touch while controlling how many enemies can surround you at one time.

It’s brilliant, really.

Nearly Immortal

At 11th level, you can choose to drop to 1 Hit Point instead of 0 if you are overwhelmed in combat or fall victim to a trap. This means the enemies have to kill you 11 times before you actually die.

This can vary, however, depending on how many ki points you have remaining in the combat, but if you are judicious, this could really annoy your foes. It could also be the last-minute rush you need to run off and heal someone else who has dropped to 0.

Other options include collecting your dead teammates into a bag of holding and running away, playing dead until the enemy is distracted and then running away, or doing that really cool thing villains sometimes do when the hero only thought they killed him but instead the audience can see the villain stand up while the hero’s back is turned.

Yeah, that’s you, buddy. Get it!

The Long Death Monk’s Limitations

  • You are still a monk
  • Exclusively melee

You Are Still a Monk

Yes, monks are cool. They always have been, and, to be frank, I feel like the monk class from earlier editions has become the template from which all other classes in 5e are drawn. They have their own unique power sources, per-rest abilities, and inherent flavors.

But Long Death monks carry with them all the problems of 5e monks. They are limited in their combat versatility. They are almost exclusively melee oriented despite not being able to wear armor or carry a shield.

Long Death monk can make up for this with their boost to HP via their death touch ability, but, like all monks, their ki ability patient defense will be how they save themselves from enemies who are also quite skilled in melee.

To make up for this, you can improve your defense with feats and magic items.  

Get a cloak of displacement. That will be like spending a ki point for patient defense every round without actually using the ki point. Any other magic item that improves your AC will be a boon to you here as well.

Bracers of Defense, amulets of protection, or even expendable items that can reproduce a shield spell-like effect will serve you well.

Alternatively, you could take one of the Magic Initiate feats to access a defensive spell or two. This option will also give you a cantrip that can make up for that lack of ranged weapons you might be having. For Long Death Monk, I would recommend chill touch, but more on that below when we talk about building your monk.

Exclusively Melee

The other downside to being a monk is that you are exclusively a melee combatant unless you take care to give yourself a ranged option. Sadly, the Way of the Long Death does nothing to shore you up in this regard. Even though all of your abilities are excellent for a melee combatant, they will not help you at range.

You can overcome this! Since you won’t be spending your ki points to dodge because of the boost to HP you’ll be getting, you can use those ki points to dash and close into melee more easily than any other character.

If you want to punch someone, you have to be standing close enough to do it. Luckily, the Step of the Wind ki ability combined with the movement enhancement you gain and the ability to move over liquids and vertical surfaces will help you to get close enough.

Now, if only you could fly…

This limitation, like the lack of defense, is fixable with the right build. Scroll down to see how we address this in the following section.  

Black Citadel’s Ranking and Tier System

Color and tier ranking is very helpful when you’re trying to digest a lot of information. In our ongoing series of 5e class guides, we use the following color-rating scheme:

RedC Tier. Red options can sometimes be situationally useful and might make for an interesting narrative choice, but they are largely less effective than other tiers.

GreenB Tier. Solid but nothing that is absolutely critical for a build, or Green can be very good but only in very specific situations.  

BlueA Tier. An excellent choice. Widely regarded as powerful in some way, useful, highly effective. 

PurpleS Tier. The top of our rankings. Objectively powerful or transformative in some way.  No choice in D&D is essential, but these options are worth strongly considering when you create your character.

Our goal here is to provide scannable but comprehensive guides for you as you develop your character.

While we might sometimes make reference to unofficial or homebrew content to illustrate a point (or just because it’s too cool not to talk about), every option we suggest is legal in the official rules for D&D 5e as published by Wizards of the Coast.

Building Your Long Death Monk

What follows are the step-by-step tools you will need to build the best Long Death Monk you can build. While you will surely want to customize your character instead of taking our word for it blindly, keep these suggestions in mind as you proceed.

The first thing to consider is your martial arts lineage. Why have you chosen this subclass and what part does it play in the larger world?

This martial art is focused on creating and harnessing death energy. Who else in your world has death- or deathless-themed flavoring?

In some worlds, elves are both feared and revered by other races because of their long life spans. In Eberron in particular, they worship their “living ancestors” who have managed to stay alive so long that they become a type of radiant undead (as opposed to necrotic) called The Deathless.

Does your particular martial art descend from these elves who are so fascinated by their own semi-immortality that they can achieve a type of living perfection via their martial art and in that study have learned to call forth death in their enemies?

Is your art descended from a Vampire lord who feasts on the living and has taught his martial secrets to his followers?

Perhaps your original sensei was a lich eager to prepare his followers for an eternity as a type of advanced undead once they died?

Finally, there are also druidic sects fascinated with the death and dying cycle of the natural world. Could they be what began your tradition?

This decision should be at the forefront of your character’s build as it will guide everything that comes after.

Ability Scores

When building your Long Death Monk, you will have to choose between Wisdom or Dexterity for your highest ability score. Your ki abilities and your Armor Class will be directly affected. Ultimately it will come down to what is more important for you — offense or defense?

As for the rest of your attributes, you’ll need to decide what else you do in the party. Since, as a monk, your main role is as a combatant, you’ll need to decide how you wish to support your combat abilities.

Furthermore, if you decide to multiclass, the rest of your stats will determine how effective that multiclassing is.

Dexterity – While some disagree, we recommend making Dexterity your highest attribute with only one exception. If you are multiclassing as a cleric or a druid, choose Wisdom. Otherwise, Dexterity will be your most important attribute. It factors into your armor class and your attack and damage as well as the skills that monks can bring to the party in the way of acrobatics and stealth.

Wisdom – This needs to be your second-highest attribute even if you do not multiclass into a wisdom-based spellcasting class. A high wisdom will improve your stunning strike, your armor class, and the insight/perception skills a monk brings to the party as a forward scout.

Constitution – If you are not multiclassing into a spellcasting class, then your Constitution should equal your Wisdom in importance. The extra hit points alone are enough reason to keep this attribute high. You will be in melee at every opportunity, and you can’t dodge every attack.

Intelligence Monks are, in general, a highly educated class. Culturally speaking, they are often depicted as artists and scholars in addition to masters of self-defense. There is quite a bit that can be offered by a decent Intelligence score when you consider that monks gain proficiency in one type of artisan’s tools. As a Long Death monk, alchemist tools could be a way to make poisons or potions with DM approval.

Charisma – Long Death Monks are capable of spreading fear with an action, but when coupled with an intimidation check, you could talk your way through just as many doors as you could break down. Call it the art of fighting without fighting, of winning the battle in the mind before the first punch is ever thrown.

Strength – As a monk, your combat skills will be dependent on Dexterity, and your athletics skill will be neglected in favor of your acrobatics. Additionally, at 9th level, you won’t ever need to climb again thanks to your unarmored movement. Mechanically, there is little that Strength can offer you.

Races

Your race is one of the most important decisions you can make. The extra abilities granted by this choice and the accompanying stat bonuses will determine what your main tactical decisions are.

Goblin – When it comes to mechanics, goblins make surprisingly good monks. Their fury of the small ability will consistently grant you extra damage in melee, and their nimble escape will free up your ki points to use on flurry of blows. From a flavor perspective, goblins can make an excellent choice for the Way of the Long Death. Goblins are absolutely a warrior culture with loads of dark gods that can transfer well.

Humans – The whole point of the Human race in D&D is that their versatility makes them amazing at any class you choose. What makes them especially good for monks is the additional feat they get at 1st level. If chosen carefully, you can set up your human monk to have all of the bells and whistles you would get from multiclassing.

Backgrounds and Feats as a Type of Multiclassing

Multiclassing is always a hard decision, but it is one that can be avoided if you are a variant human.

For example, you could multiclass into rogue, OR you could take the criminal background and the poisoner feat. You will gain proficiency with thieves’ tools, stealth, sleight of hand, and benefits with poison without sacrificing your monk levels.

Similarly, instead of multiclassing into sorcerer or wizard, you could take proficiency in alchemist supplies from the monk class, proficiency in Arcana from the scholar background, and then two cantrips and a 1st-level spell from the Magic Initiate feat. Granted, you won’t be slinging fireballs every round, but you can sling a green-flame blade and still get your unarmed attack while concentrating on a hex spell.

Warforged – Warforged also make great monks. Their inherent +1 to AC and ability to meditate instead of sleep give them some natural overlay with the monk class. You also gain proficiency in a skill or two of your choice and have the option of giving your character the single-minded focus on martial arts that only a neurodivergent construct can have. When combined with the fascination with death that Monks of the Long Death carry, what you have is a disciplined character who knows how best to create death among the fleshies since death is so rare among the warforged.

Wood Elves – Like all elves, wood elves gain a bonus to dexterity and to wisdom, the two most important attributes for a monk. In addition, they lend themselves to the monk class because of their unique sleeping requirements and because of the weapon proficiencies that are normally denied to monks. It is also important to note that wood elves are also given the option to take the Wood Elf Magic feat, which grants two druid cantrips and the longstrider and pass without trace spells. If you take shillelagh and any other cantrip, you have just made your staple monk weapon, a quarterstaff, into a 1d10 magical bludgeoning weapon.

Backgrounds

Your background will grant you skill, tool, and roleplay features that will inform where and how your Long Death Monk functions in the party.

Acolyte – Way of the Long Death monks are inherently a religious sect if you follow the rules in which they are presented. As such, the Acolyte background will provide you with a nice feature called shelter of the faithful that will provide you and your companions with a safe haven in between adventures. In addition, you will receive two languages and the Insight and Religion skills.

While this is not a mechanical bonus that translates to combat very well, it will serve an important downtime function and be a source for resources and plot hooks during your character’s career.

House Agent – Even though this is an Eberron-specific background, you could easily say that it is the background of your school or temple and the features would still work the same way.

When you choose this background, be sure to find one that has a tool proficiency you can use. Specifically, I recommend House Thuranni. The elves of House Thuranni have proficiency in the poisoner’s kit which, while not a requirement for your monk, could still be an extra little power boost that fits the flavor of a death fanatic.

Skills  

Monks gain access to Acrobatics, Athletics, History, Insight, Religion, and Stealth.

Acrobatics – This is almost always the best skill for a monk of any kind to have. It will make you safer in grappling and will allow you to make the most of that famous movement capability of your class.

Stealth – Another staple of the monk class since you need to take advantage of your full movement capabilities. By the time you are in Tier 2, you will be able to stealth as quickly as most other characters can run, which means you will be involved in more ambushes while in melee as a Long Death Monk.

Insight – This skill is also great to have if you can swing it. A good Insight check will allow you to see which of your foes is nearer to the threshold of death, thus allowing you to focus your attacks and gain the benefits of their demise.

Religion/History – These skills are a benefit to your downtime activities and will definitely add flavor to your monk, but they are not life or death. If you can get them with your background, great!

Athletics – This skill can usually be swapped out for an acrobatics check in most situations and by 9th level becomes obsolete entirely.

The Medicine Skill

The Medicine skill is a great skill for Way of the Long Death Monks to have. While at first many may say that these monks are more interested in killing than in healing, the truth is that they are fascinated with death and dying. Illness and the healing process are times when people approach the doors of death slowly and waver near its threshold.

Long Death Monks would absolutely be interested in this. Furthermore, medicine is a great tactical skill to have. As a character with a focus on death, it can be up to you to decide to withhold the blessed death from your party members.

Feats For Your Monk

Magic Initiate (Druid) – If you are not multiclassing into druid, then you should absolutely take this feat. The shillelagh cantrip will take your basic monk weapon and turn it into a d8 or d10 (quarterstaff, two-hands) in magical damage. After that, you can take the produce flame, infestation, or magic stone cantrips to help your lack of ranged attacks as a monk. I recommend the magic stone cantrip as it will allow you to use a sling, which is already a monk weapon.

After that, you can take literally any spell from the druid spell list and use it since Wisdom should already be a high attribute for you. Personally, I recommend faerie fire or entangle since those will help you while in melee.

Polearm Master – This is another great choice for monks who use quarterstaffs. While the extra attack as a bonus action is unnecessary, the ability to get in an extra shot as a reaction is a nice little oomph to your melee abilities — especially if you’ve cast shillelagh already. Just saying.

Multiclassing Your Monk

Depending on your role in the party, multiclassing may be an option you want to consider. Below we have three options for you, and each one will put you in a different place on the battlefield.

Druid – Druid is, hands down, the single best multiclass option for a monk. The shillelagh and magic stone cantrips will ensure you can keep up your damage output while maintaining the relevance of your martial arts. In addition, your martial arts abilities can still be used in wild shape, provided you still have limbs with which to make your natural attacks.

However, the reason why druid is the best multiclass for the Way of the Long Death monks is because of the Circle of Spores subclass. With the Circle of Spores, you will be able to add necrotic damage to all of your melee attacks, which not only improves your already substantial melee presence but also gives you a thematically appropriate damage type: necrotic.

At 5th level (2 druid / 3 monk) in this build, you can, while in your Circle of Spores wild shape, make a melee attack with your shillelagh quarterstaff, spend a ki point as a bonus action to make two unarmed attacks, and use your reaction to deal damage with your spores all while adding necrotic damage!

Therefore, in one round, you will roll 1d10+1d6 (shillelagh quarterstaff/spores), 1d4 + 1d6 (unarmed attack/spores), 1d4+1d6 (unarmed attack/spores), and 2d4 (reaction with spores).

To see it more clearly, that’s 1d10+2d4+3d6 on your turn and +2d4 as a reaction.

Rogue – The rogue is a great multiclass for every monk. The movement abilities and the cunning action ability lend themselves quite well to the monk’s natural tendency to take several actions and move around the battlefield.

Sneak attacks also never hurt anybody. Well… I mean, it does hurt those bad guys, at least. And that’s the point! As a monk, you have the ability to disguise yourself without having to hide a giant ax behind your back. You can pretend to be a servant, a scholar, a dignitary, or even a harmless beggar and still be dangerous with your unarmed strikes added to sneak attack.

The rogue subclass that pairs best with the Way of the Long Death is the Assassin. With their ambush abilities, you can drop a form in the first round of combat and set yourself up with those temporary Hit Points right off the bat.

Ranger – This is an excellent choice for all the same reasons a rogue is an excellent choice. It has stealth-based abilities and solid melee support. It also has the added benefit of spellcasting and, with the Druidic Warrior fighting style, you can get access to the wonderful shillelagh spell that seems like it was made with monks in mind.

The best subclass for Way of the Long Death monks to multiclass into with ranger is easily the Gloom Stalker, which, like the assassin, can give you a great bonus in the first round of melee that will allow you to drop one of your foes and get those temporary HP in early.

Progression Example: Long Death Monk Build From Tier 1 – 4

Bonepicker is a goblin of the dark-tunnel clan. Fascinated with the idea that life continues in a rolling wave surrounded by death on either side of it and that the life of his clan is supported by such a wave through time and waves roll over the ocean, Bonepicker could often be found in the bone pit where the Dark-Tunnel clan threw their dead.

Bonepicker spent most of his time raiding with the other goblins of his clan. When he realized he was unique among his family and that his single-minded focus on creating death made him different from his peers who would simply kill to eat, Bonepicker left to roam both the surface and the Underdark in order to find ways to study and harness the unique energy of death.

Players can find Bonepicker at any point in this journey.

Tier 1

  • Granted Subclass Abilities: Touch of Death
  • Backgrounds, Proficiencies, Feats, or Ability Scores Improved: Hermit, Medicine, Acrobatics, Survival, Stealth, Herbalism kit, Magic Initiate (Druid)
  • Favored and Special Gear: Quarterstaff with shillelagh at 4th level, a crude journal with drawings of various creatures’ anatomy, goodberries at 4th level

In Tier 1, Bonepicker is wandering the land. Still weak enough to be cautious and terribly shy, Bonepicker often finds dead and dying creatures and makes his own study of them. He draws their anatomy and takes notes of their dying process. This study of life and death while roaming the wild has given him a relationship with the natural world and is the source of his Magic Initiate (Druid) feat.

Tier 2

  • Granted Abilities: Hour of Reaping
  • Backgrounds, Proficiencies, Feats, or Ability Scores Improved: Improved Dexterity and Wisdom by 1.
  • Favored Equipment: Healing potions, Shillelagh staff, Bag of tricks (brown)

At Tier 2, Bonepicker hasn’t much need for treasure or equipment. If he happens across serious loot, he isn’t above selling the information to adventurers for gold, which he turns around and uses to buy supplies for extended camping and fieldwork.

He is confident enough in his abilities at this point to even try signing on with adventurers himself if he thinks they won’t try to kill him. To that end, he will work as an underground guide or forward scout. His main goal for working is not the glory or the riches but to attempt to discuss his studies with healers, philosophers, theologians, or necromancers. He wants to broaden his scope of study into the magical and spiritual realm if possible.

Tier 3

  • Granted Abilities: Mastery of Death
  • Backgrounds, Proficiencies, Feats, or Ability Scores Improved: Polearm Master
  • Favored Gear or Equipment: Holy book or sacraments of a death cult; notes on different martial arts techniques designed to maim or kill outright; Shillelagh staff, healing potions, poisoned darts; one dart of Slaying for several different types of humanoids and creatures in your game.

In Tier 3, Bonepickers wisdom and skill have progressed to reputable levels. Bonepicker is willing to take on students, though he requires they be able to travel with him. In order to train or study with Bonepicker, prospective students must demonstrate a philosophical understanding of death and bring him a Dart of Slaying crafted from the bone of a creature they have killed themselves as a gift to show their dedication. If the creature has no bones, the prospective student is expected to use their imagination in completing this requirement.

Tier 4

Granted Abilities: Touch of the Long Death

Backgrounds, Proficiencies, Feats, or Ability Scores Improved: Improved Dexterity and Wisdom by 1.

Favored Gear or Equipment: No less than 12 Darts of Slaying for several different creatures in your game, a complete manuscript for Bonepicker’s martial arts style and school, bag of holding, Staff of Withering, a shillelagh staff, Cloak of Displacement, Carpet of Flying, and a tent that casts tiny hut once per long rest.

At Tier 4, Bonepicker’s reputation has spread to the point that powerful spellcasters, warlords, and even a lich or two have sought him out and presented him with wondrous gifts in exchange for his willingness to come and teach their soldiers and minions. Bonepicker accepts his gifts and will teach any who come to him for knowledge. However, he will not be tied down permanently, and he waits patiently for the day when his death will come in due time.

Until then, he will always wander in search of new and rarer creatures to add to his journal.

A Beginner’s Guide To Playing a Long Death Monk

Monks in general are both an easy and a difficult class to play. They are easy because your goal is simple: get into melee range, and attack as much as you can.

That being said, monks are capable of so much more once you learn how their abilities work.

You can use the step of the wind and the patient defense abilities to do all of the other important goals in a typical adventure while your party members are concerning themselves with combat. If done right, you can run through a crowded battlefield, secure the MacGuffin and get back out again without taking a single point of damage. You might even be able to do it unseen.

Playing a Way of the Long Death monk, however, cements your role in the party as a primary melee combatant. Unlike most monks, however, you will have the nifty Touch of Death ability that will give you endurance in a fight. Temporary Hit Points can save you in a pinch.

The important thing to remember as a Way of the Long Death monk is that you will be a versatile combatant — the one who can move in and out of danger to distract your foes, protect your allies, and be an all-around badass while you do.

Death Is the Natural State

Playing a Long Death monk doesn’t necessarily mean you will be a creepy edgelord with a penchant for things that go squish in the night. Neither do you have to be some necromancer’s bodyguard.

Although you could if you wanted.

For a Long Death monk, death is a natural process that should be understood and harnessed on the path to personal actualization. This doesn’t mean you have to be immortal or pursue some kind of eternal undeath as a lich or a vampire.

Although you could if you wanted.

Rather, death is to be observed and respected, and when you bring holy death to a creature, it is best to honor them as they make the journey we all must make eventually. You don’t have to be a trophy hunter who collects dead bodies in a bag of holding in order to pay some kind of debt to a lich in exchange for an eternity as a sentient undead or extra decades of life.

Although… you get the idea.

At Higher Levels

If you do successfully play a Long Death monk to higher levels, you should consider multiclassing after 11th level. Waiting until after 11th level grants you the Master of Death ability, which is unlike any other in the game in power and frequency.

If you do multiclass, obviously for reasons I posted above, I recommend picking up levels in druid, rogue, or ranger.

However, if you are comfortable at that point with taking some risks for flavor’s sake, feel free to give Cleric of the Grave or Shadow Sorcerer a try. Both are spellcasters who can provide nice boosting spells to yourself and your allies, although at that point you will be sacrificing the melee capability that is your hallmark.

Remember…

Have fun, roll well, and come back to the Citadel whenever you want to explore something new.