D&D 5e: Way of the Long Death Monk Guide

D&D 5e: Way of the Long Death Monk Guide

Role in the Party

The Way of the Long Death Monk is a simple and bizarre monk subclass. The flavor text describes how they do experiments on creatures and watch them die, and this somehow gives them magical martial arts powers.

Monks in general have problems, but a good subclass can turn them into okay characters at most tables. Way of the Long Death is weird since every feature could be pretty good but has problems. In general, you will be a more durable monk that does normal monk activities (weapon and fist-based homicide), and depending on your level, you will have one or two unusual actions you can take in addition to your normal attacks.





The Way of the Long Death Monk subclass is found in the Sword Coast Adventurer’s Guide. Click here to pick up your own copy of the Sword Coast Adventurer’s Guide!

Way of the Long Death Features

Touch of Death

Starting when you choose this tradition at 3rd level, your study of death allows you to extract vitality from another creature as it nears its demise. When you reduce a creature within 5 feet of you to 0 hit points, you gain temporary hit points equal to your Wisdom modifier + your monk level (minimum of 1 temporary hit point).

This is a decent feature that gives you a respectable amount of temporary hit points. Now that I think about it, this feature sounds familiar… hey! This is the Fiend Warlock’s level 1 feature.

Unlike the warlock, this feature has a range of 5 feet, but most monks are melee characters anyway. It also doesn’t say “hostile creatures”, so you could use it on non-hostile creatures. The utility of this is questionable, but the wording means that you can more easily carry around a bag of rats and punch a rat every time you need temporary hit points. This is sort of cheesy, so talk to your dungeon master, but I’d allow it since it fits the theme of slaughtering creatures to steal their life force.

Hour of Reaping

At 6th level, you gain the ability to unsettle or terrify those around you as an action, for your soul has been touched by the shadow of death. When you take this action, each creature within 30 feet of you that can see you must succeed on a Wisdom saving throw or be frightened of you until the end of your next turn.

You can use an action to frighten every enemy within 30 feet of you? And this doesn’t cost ki or have limited uses? This is almost an amazing feature, but it has friendly fire! Unless your fellow melee allies are immune to the frightened condition, this has a chance to debuff them every time you use it. If you’re the only melee character in a party of spellcasters and archers, this is still a bad idea since running at all the enemies will usually result in you dropping to 0 hit points.

You could have your ally look away from you when you take this action, but the rules on that are unclear, and in D&D, it’s generally assumed that everyone is looking around everywhere all the time in combat. If this is possible, or if all your allies are immune to the frightened condition, or if your melee allies are all clerics using Spirit Guardians (unaffected by being frightened), this is an Epic feature, but otherwise, the friendly fire sucks and you will only be able to use this some of the time. It is free though.

Mastery of Death

Beginning at 11th level, you use your familiarity with death to escape its grasp. When you are reduced to 0 hit points, you can expend 1 ki point (no action required) to have 1 hit point instead.

Have 5 hit points? Just took 500 damage from being shot in the face with a nuclear weapon? Expend 1 ki point to have 1 hit point left instead; instant death rules don’t even apply since you aren’t reduced to 0 hit points. Then when the second nuke hits you in the face, you can spend 1 ki point to still have 1 hit point left instead. In more realistic scenarios, this is excellent against powerful one-hit damage effects like a Finger of Death or a dragon’s breath weapon. This is less effective against multiattack combos though; the Tarrasque has five attacks, and if it hits you five times, you need to spend 5 ki to not die. Watch out for mariliths!

Touch of the Long Death

Starting at 17th level, your touch can channel the energy of death into a creature. As an action, you touch one creature within 5 feet of you, and you expend 1 to 10 ki points. The target must make a Constitution saving throw, and it takes 2d10 necrotic damage per ki point spent on a failed save, or half as much damage on a successful one.

20d10 necrotic damage sounds good at first, but the problems are the saving throw and the ki cost. Any enemy worth using this on at level 17 has either a great constitution saving throw bonus, legendary resistance, or both, so they’ll usually pass. On a pass, that’s 55 necrotic damage. On a fail, that’s 110 necrotic damage. If the enemy has a 70% chance to pass and we’re ignoring legendary resistance, that’s 77 average damage. For ten ki. At least we can use Ki Empowered Strikes to add a bonus action attack that’ll deal about 7 more damage with a 65% chance to hit.

I’ve seen some rare builds that can do more than 84 DPR every round at these levels, and a fighter’s action surge is definitely doing more damage than your 10 ki nova. Soon, the fighter will have two action surges!

We could get 20 extra bonus action attacks with that ki for roughly 130 damage with a 65% chance to hit on each attack or stun the enemy with Stunning Strike using the same saving throw DC.

In conclusion, this is an awful feature and it’s a trap to use unless you somehow have infinite ki. If you have infinite ki, just spam your other ki-hungry features instead.


You’re more durable than the ordinary monk; significantly so at level 3 and dramatically so at level 11, and starting at level 6, you have an unusual and possibly powerful option that can be made effective in the right party.


Your damage isn’t going to be great, and it’s going to feel awful when allies “steal” your kills and deny you temporary hit points, and trying to strategize so the enemy lives long enough for you to finish them off also hurts. There are also a lot of party compositions where your level 6 feature just isn’t viable at all.

Best Race Options

I saw some really cool art of a spooky death-themed Tortle once and now I can’t help but imagine the tortle on all the death-related subclasses. There is no mechanical reason to take the tortle, except for extra unarmed strike damage at levels 1-4 and the emergency Shell Defense.

Tabaxi will give you the speed you need to sometimes land an Hour of Reaping aura without affecting your teammates. Hopefully, enough enemies are frightened to where they can’t surround you.

Shadar-Kai have useful teleportation abilities, and their Trance lets you have proficiency in the longsword and/or Warhammer, then make it into a monk weapon at 2nd level with the Tasha’s optional class features. Shadar-Kai are also spooky shadow elves who have strong ties to death, and resistance to necrotic damage is nice too.

Choosing the Right Skills

Perception is the most important skill in the game, and Insight is a useful skill that your wisdom score allows you to be great with. Animal Handling may be necessary if you want to lure rats into your bag of rats.

Acrobatics and Athletics are both solid proficiencies for you. It sucks to have a -1 to athletics check as a powerful martial artist, and Acrobatics is also extremely useful.

Arcana is suitable for anyone researching dark arts, and Intimidation lets your life force-devouring death monk be intimidating. It’s pathetic to have a -1 to intimidation checks as a Long Death Monk.

Fitting Feats

Shadow Touched is an excellent half feat that can boost an odd wisdom score, and it gives you the Invisibility spell and another spell from a small pool. Silent Image is a good pick from that list; illusions are always handy.

Elven Accuracy is one of the best ways to boost your mediocre damage. An increased chance to hit and crit will lead to a moderate damage boost, and it’s a half-feat. Unfortunately elf-only, but at least Shadar-Kai count as elves.

Telepathic is a wisdom-boosting half feat that can give you telepathy and the ability to read minds. Perfect for a spooky monk.

Optimal Backgrounds

Pick Haunted One for maximum edge; perhaps your Harrowing Event involved massive death and destruction and made you obsess over death.

Nobody wants to hang out with creepy Long Death Monks, and their deathly experiments are illegal in many civilizations. Perhaps you were a Hermit who lived on their own to pursue their research or with a very small community of like-minded monks.

Not all tables use feat-granting backgrounds, but if yours does, Wildspacer is just free hit points for you due to the free Tough feat. Also, zero gravity situations don’t impose disadvantage on your melee attacks, so you can punch people in space.

Multiclassing Options

One level of Undead Warlock lets you try to frighten enemies on a hit with your Form of Dread. It’s also a great way to fill an empty bonus action left by your Hour of Reaping ability.

Three levels of Gloom Stalker Ranger will let you be invisible to most creatures while in darkness, and it offers excellent first round extra damage potential while granting a smorgasbord of other benefits.

One level of Barbarian for Rage after level 6 may be a good idea. It helps you survive botched Hour of Reaping attempts by granting resistance to a lot of the damage you take from the enemy hordes descending upon you. Even if you can’t benefit from the armor proficiencies or extra rage damage, it’s still a useful ability.

Would I recommend playing a Way of the Long Death Monk?

It takes specific kinds of tables for the Long Death Monk to shine. They do fine in unoptimized parties, as well as parties that have a way of negating the friendly fire potential of Hour of Reaping.

I wouldn’t recommend one at very high levels due to the exceptionally low damage of high level monks and the poor capstone, and I wouldn’t recommend it at optimized tables; go with a Necromancy Wizard or Undead Warlock or another class/subclass combo if you want to play a death-obsessed lunatic.

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