Way of the Shadow Monk, they’re a sulky bunch. A ninja, even. If you’re a little bored of playing a Rogue, but you still love the sneaking and surprising, then you should definitely look at playing this Monk subclass. It’s loaded with features that allow you to be at one with the shadows, diving and jumping in the darkness.

Way of the Shadow Monks is quite heavy on the sneaking and not-being-seen. This Monk subclass also has a couple of nice offensive bonuses but lacks the extra skill sets that a Rogue has. Plus, you don’t get that sneak attack and damage, and you may struggle to disarm traps and open locks.

With a few well-placed feats, you can really make the most of the Way of the Shadow. You are the night that walks unseen amongst the gangs of Dock Ward. You are the Way of the Shadow.

To learn about the Monk class in general, you can check out our Monk Guide here.

How to Use This Guide

Everything in this guide has an emoji, ranking how useful a given ability or feature is to playing this class effectively.

✅ — An absolutely crucial feature. Often forms the backbone of a class’ look and feel. Will provide some bonus that can’t be found through other means.

🆗 — A solid feature that does its job well. Not game-breaking, and certainly replaceable, but a strong choice that shores up some weakness.

⚠️ — A debatable choice. Could work for a specific build, but otherwise is either a wasted opportunity or is just weaker than other alternatives.

⛔ — Outright bad and detrimental. This weighs down the class and just takes up space on the character sheet. A weakness you will have to accommodate for.

These rankings are meant to help you create an optimized class build, but remember, DnD isn’t a game where you need to win to have fun. Weaker but flavorful builds also have their place and can make for fulfilling characters.

These rankings are in relation to the Way of the Shadow Monk build. Check out our guide on Monk subclasses, which gives a rundown of all the Monk archetypes.

How To Play A Shadow Monk

Shadow Monks are a bit of a sneak-and-strike Monk, and are found in the Player’s Handbook. Their offered abilities give you the best chance of sneaking up on an enemy and giving them a good thumping before they even know it.

The Shadow Monk’s skills are also great for infiltration and getting you into places you shouldn’t. Add Darkvision into the mix, and the darkness is your friend. Hello, darkness, my old friend.

Shadow Monk Subclass Features

Level One (Monk)

✅ Unarmoured Defense

No armor for a Monk build. Your wit and fluid movement are your armor. Your AC is 10 plus your Dex modifier and Wisdom modifier. This is why it’s essential to have the highest Dexterity and Wisdom scores.

✅ Martial Arts

Thanks to your training, you gain the ability to use your hands, feet, elbows, knees, and all the body parts as your weapons. The main points of martial arts are:

You use Dexterity instead of Strength for attack and damage rolls for your unarmed strikes and Monk weapons. Why Dexterity is important!
You start off with D4 damage on your unarmed strikes or Monk weapon. This increases through the levels.
If you use your action to attack, you can use your bonus action to make an extra unarmed attack as long as you haven’t already used your bonus action. Two attacks at level one. Crazy!

Level Two (Monk)

✅ Ki

You gain the ability to channel Ki through your body and soul. It’s what surrounds us and binds the galaxy together. Hang on, that’s the force. You get so many Ki points per level, starting with 2 at level 2. Then 3 at level 3, 4 at level 4. You get the idea.

Ki points are spent on Monk skills and Monk subclass skills. Shadow Monks have some skills that Ki points can be spent on.
You need to have a long or short rest to regain all your Ki points.
Some Ki bonus skills require the target to make a saving throw. To work that out, your Ki save DC is 8 plus your proficiency bonus plus your Wisdom modifier. Again Wisdom is important.

🆗 Flurry of Blows

This skill allows you to spend a Ki point and get two more unarmed strikes as a bonus. So essentially, three attacks at level 2. Goodness me! You CAN’T attack, bonus attack, and then spend a Ki and get two extra attacks. It’s one or the other. At low levels, it can eat up your Ki quickly. Use sparingly.

✅ Patient Defense

Spend a Ki and get the Dodge action as a bonus action. Duck, dive, dodge, especially if you’re low on health.

🆗 Step of the Wind

Get the Disengage or Dash action as a bonus action when you spend a Ki point on your turn. Also, your jump distance is doubled for the turn. Nice! Comparable to a Rogue’s cunning action, but with the cost of a Ki.

🆗 Unarmored Movement

Extra speed is nice. Starting with +10ft at level 2, it goes up to +30ft at level 20, and the ability to walk on liquids and along walls at level 9—parkour for the Monk.

✅ Dedicated Weapon (Optional)

After a short or long rest, you can touch a weapon, focus your mystic Ki, and count that weapon as your Monk weapon until you use this feature again. This opens up a whole host of weapon possibilities.

The rules are as follows:

The weapon must be simple or martial
You must be proficient with it
It must lack the heavy and special properties

Adding a Longbow to a Shadow Monk build can make you into a really effective long-ranged character without deviating from the usual melee Monk punch ninja.

Level Three (Way of the Shadow and Monk)

Here we are, this is where you get to choose your Monk’s monastic tradition. And we choose Way of the Shadow.

Shadow Arts

You get some excellent Monk-like spells. Four spells and a cantrip. You cast these as part of an action. The spells cost 2 Ki.

✅ Minor Illusion

Firstly, you get this little distraction nugget. You can create a sound or small image up to 30ft. An absolutely fantastic feature for misdirection.

🆗 Darkness

Create your own shadow. You can project darkness up to 60 feet away. Darkvision can’t see through it, so it’s more of a way of escaping.

✅ Darkvision

Boom! 8 hours of Darkvision. An essential feature for a shadowy figure.

✅ Pass without Trace

+10 to your sneak skill. Yes!

✅ Silence

Create a sphere of silence 20ft radius. Great for disarming spellcasters.

⚠️ Deflect Missiles

The ability to catch an arrow AND potentially throw it back at your assailant is quite the feat. Firstly, you can use your reaction to reduce the damage. You work that out by using 1d10 + your Dexterity modifier + your Monk level.

Here’s the clever bit: if you reduce it to 0, you catch it and get to make a ranged attack with a range of 20/60. You spend 1 Ki point to do this.

✅ Ki-Fueled Attack (Optional)

Spend a Ki point and make an unarmed or Monk weapon attack as part of a bonus action. But what about Martial arts bonus attack? Isn’t it the same?

No, the main differences are:

Martial arts – If you use your action to make an attack, you can use your bonus action to make an extra unarmed attack.

Ki-Fueled Attack – Your first action doesn’t need to be an attack. You could cast one of your Shadow Monk spells AND attack unarmed OR with your Monk Weapon.

So you could cast darkness and then punch your foe with a Ki-fuelled attack. And they wouldn’t even see. Shadowy goodness.

🧘 The Shadow Monk isn’t your jam? Discover our guide to playing Astral Self Monk

Level Four (Monk)

⚠️ Slow Fall

Very rarely will this happen, but you can reduce falling damage by an amount equal to 5 times your Monk level. If you’re shadowing around a cliff or something?

⚠️ Quickened Healing (Optional)

Healing is always good. Spend a couple of Ki, and roll your martial arts die. You gain hit points to the number you rolled plus your proficiency. Bit Ki heavy.

Level Five (Monk)

✅ Extra Attack

Instead of one attack, you now get two. You can also add your bonus action attacks on top of Flurry of Blows, equaling three or four attacks, respectively.

✅ Stunning Strike

When you attack with a melee strike, you can spend a Ki and perform a stunning strike. The foe must make a Con save or be stunned till the end of your next turn. Being a ninja is an essential feature. Sneak in, stun your enemy, and do away with them. Disappear. Have a sandwich.

🆗 Focused Aim (Optional)

You go to strike and miss. Focused Aim allows you to use up to 3 Ki points to push that attack roll over the AC. Each Ki is worth 2 points. If you’re sneaking up on a guard, this could be crucial to knocking them down.

Level Six (Way of the Shadow and Monk)

🆗 Shadow Step

Basically teleportation. You can jump from shadow to shadow up to 60ft. You also get advantage on the first melee attack. Add Stunning Strike, and you can easily sneak up on your enemy and retire them.

✅ Ki-Empowered Strikes

Your strikes are now classed as magical weapons. Handy! Saves the expense of getting or finding a magic weapon.

Level Seven (Monk)

✅ Evasion

You’re now able to dodge out of the way of AOE, such as fireball, for example. Make a Dex save on a fail you take half damage, and if you succeed, you take none. Because you’re a Monk and you have high Dex , this is brilliant. If you don’t have high Dexterity, you probably shouldn’t be a Monk.

🆗 Stillness of Mind

Very situational. Use your action to stop an effect that’s making you charmed or frightened.

Level Ten (Monk)

🆗 Purity of Body

Immunity to disease or poison. Poison comes up in DnD more than you think.

Level Eleven (Way of the Shadow)

✅ Cloak of Shadows

Invisibility, my friend. You can use an action to become invisible in dim light or darkness. Stay like this until you make an attack, cast a spell, or end up in bright light. Great for sneaking about on those foes. Doesn’t work too well in the sunshine.

Level Thirteen (Monk)

⚠️ Tongue of the Sun and Moon

Touch a person, and you can understand their language and speak to them. Chances are you have someone in the party that can do this anyway. It’s not going to help you sneak in the shadows.

Level Fourteen (Monk)

✅ Diamond Soul

Get proficiency on all saving throws, and you can spend a Ki to reroll should you fail. Fantastic for any Monk build.

Level Fifteen (Monk)

⛔ Timeless Body

Can’t be aged magically, and you don’t need food or water. Half of my roleplaying downtime is sitting in a tavern with my party, drinking and eating. Extremely situational. I will say, our party was aged magically, but it’s a rarity.

Level Seventeen (Way of the Shadow)

✅ Opportunist

I love this feature and it doesn’t even involve sneaking or being invisible. If a creature or foe is hit by an attack within 5ft of you, you can use a reaction to give it a jolly good Monk punch. Not shadow-like at all, but a nice leveled feature for the Way of the Shadow.

Level Eighteen (Monk)

🆗 Empty Body

Spend 4 Ki points and become invisible for a minute. You can only take force damage. For a Way of the Shadow build, you already get the Cloak of Shadows feature. The only advantage is you can do this in daylight.

Spending 8 Ki points grants you the Astral Projection spell. You can go and visit the other planes. Nice.

Level Twenty (Monk)

✅ Perfect Self

If you have no Ki points at the beginning of combat when you roll initiative you get 4 Ki points. As a Shadow Monk, this could be the difference between life or death. Use them to cast darkness and silence. Turn invisible and get the hell out of there.

The Perfect Shadow Monk Build

There are a number of things to consider when building your Way of the Shadow Monk. The character will likely be sent ahead to scope out different areas. Or even act as an assassin. You don’t have many skills to start with, but choosing the right feats, background, and race can really bump this up.

Ability Scores

⚠️ Strength

Not super important for Monks as they’re Dex heavy. Although they do have Strength saves.

✅ Dexterity

Essential for all Monk builds, especially Way of the Shadow.

🆗 Constitution

Important for every class. You do a lot of up-close combat, even when you’re sneaking.

⛔ Intelligence

Monks just need to be wise, not intelligent.

✅ Wisdom

A lot of Monk modifiers rely on this ability score. Number two after Dexterity.

⛔ Charisma

Not essential at all. Let the Bard do the talking.

Racial Considerations

I’ve picked the top races I believe to make an excellent Shadow Monk. Dexterity and Wisdom modifiers are a must with other additional bonuses.

✅ Aarakocra

With a +2 to Dexterity and a +1 to Wisdom, the Aarakocra is a sure choice. And you can fly. Yes. Cast darkness, swoop in, punch, and swoop out again. Great for infiltrating tall buildings such as Wizard towers.

🆗 Halfling – Ghostwise

A +2 to Dexterity and a +1 to Wisdom are great. Plus, you get Lucky, which lets you reroll on an attack of 1. You also get advantage against being frightened. And with the Ghostwise Halfling, you get Silent Speech, which allows you to speak telepathically to a creature within 30 ft, as long as you share a language. Great for skulking about.

✅ Elf – Wood Elf

With a +2 to Dexterity and a +1 to Wisdom, again you’re getting the right ability score increases. Darkvision means you don’t have to spend Ki on casting the Shadow Monk Shadow arts spell.

You have proficiency in the Perception skill, which is great for scoping out areas or creatures if you’re skulking ahead. Advantage on saving throws against being charmed, and magic can’t put you to sleep. Also a bonus.

🆗 Human Variant

If you get good ability score rolls, consider a human variant. Two +1 increases on any ability score, one skill, and a feat. The extra skill is handy, and feats are super important for Monks to flesh out the character. Also possibility of a feat that adds one to either Dexterity or Wisdom.

✅ Kenku

Kenkus are born Shadow Monks. As well as the standard +2 to Dexterity and a +1 to Wisdom, you get two extra skills from Acrobatics, Deception, Stealth, and Sleight of Hand. Your mimic ability works wonders for confusing creatures as you sneak up to them and punch them dead.

Notable Backgrounds

🆗 Criminal

You get a set of thieves tools and the skills of Stealth and Deception.

✅ Charleton

With a forgery and disguise kit, plus Deception and Sleight of Hand skills, this background is great for a Shadow Monk.

✅ Urchin

Probably the best background for the Way of the Shadow Monk. Not only do you get skills in Sleight of Hand and Stealth, but also tool proficiencies in thieves tools and the disguise kit. Getting that prof in thieves tools allows that Monk/Rogue crossover without multiclassing. A shadowy thiefy Monk.

Shadow Monk Skills

Depending on your background and race choices, you can end up with a fair few decent skills. You get to choose two from Acrobatics, Athletics, History, Insight, Religion, and Stealth.

We recommend Stealth as a must and either Acrobatics or Athletics. Insight is great for scoping and understanding people’s motives or personalities. History and Religion are good RP skills if your race and background allow more skills.

🧘 Want to discover another subclass? Check out our guide to playing Open Hand Monk

Best Feats for Way of the Shadow

Feats are great and can really give your character legs. However, getting your Wisdom and Dexterity to the max is important to get the best out of your Way of the Shadow build. Monks get four feats or ability score improvements throughout their leveling.

🆗 Alert

Add +5 to your initiative, no one can surprise you if you’re awake, and any creature that is hidden and attacks you doesn’t gain advantage. Having that +5 to initiative makes perfect sense if you’re sneaking up on an enemy and it goes awry. Whether it’s to get the first punch in or get the hell out of there, going first could be the difference between life and death.

I like this skill. My Gloom Stalker Ranger just acquired it, which gives him a +12 initiative. With the crossbow expert, you’ll be riddled with bolts before you can say “Hello!”

✅ Crusher

Top skill right here. You get to increase your Str or Con by +1. Unless you’ve got a good con score, drop this in Constitution rather than Strength. Once a turn, if you hit a foe with an attack that causes bludgeoning damage, like fists, you can move it 5ft to an unoccupied space or off a cliff, for example. If you score a crit that deals bludgeoning damage, all attack rolls against that foe have advantage.

🆗 Durable

With Constitution being 3rd most important of your ability scores and with a Monk only getting d8 hit points, upping your Constitution any way possible is great. And adding that hit point mod on a short rest makes sure you get up to full HP real quick.

🆗 Observant

Increase your Wisdom by +1, you can lip-read a language you know, and you get a lovely +5 on your passive Wisdom (Perception) and passive (Investigation). That +1 to Wisdom is great. The passive perception and investigation are perfect for scoping out places.

✅ Skill Expert

Gain a +1 to any ability score, proficiency in a skill, and expertise in any skill you have proficiency in, which doubles it. If you’re lacking in skills and still need to up an ability score, this is perfect for your build.

✅ Tough

As a Way of the Shadow Monk, you’re sometimes a bit on the front line, so being tough is essential. Your Hit point maximum goes up by an amount equal to twice your level, and at every subsequent level, your hit point max goes up by 2 points. Tanky Monk.

Weapons and Armor

You have fists. Ok, so one weapon I would definitely invest in is a longbow. Should you be required to do ranged attacks, this is perfect. You can use your dedicated weapon skill at level 2 for this.

Multiclassing

Monks work best as single-class builds. However, a few levels into Rogue won’t harm. If you don’t have a Rogue in the party, this level dip can make you the party’s Rogue-like character.

Magic Items

✅ Amulet of Health

Brings your Constitution up to 19. Anything to raise that Con.

✅ Braces of Defense

My Monk build had these, and you get a tasty +2 to AC. Great for a Shadow Monk out on their own.

✅ Manual of Bodily Health

Magical manual with delicious recipes and at-home exercises. Also raises your Con by +2.

🧘 Check out our selection of the best magic items here

Ninja Rogue in Disguise

This archetype is ideal for the player who loves the Rogue class but wants a different perspective on it. You get most of the Rogue elements with more punch. And added elements of the Ranger Gloomstalker subclass built-in.

I hope you enjoyed my article on the Way of the Shadow Monk. We would love to hear about your experience playing one yourself and if you’ve had any different experiences with your build. Tell us in the comments below.