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The Shadow Ninja: The Ultimate Stealth Assassin | D&D 5e Build Guide

Original Video:

*This article is an edited version of the script for this video


Bugbear, gives us proficiency in stealth and extra damage on the first round of combat which is both of the things we are going for on this build

Ability Scores(point buy):

Str: 8

Dex: 15(+2)

Con: 15(+1)

Int: 8

Wis: 15

Cha: 8

Ability Score Priorities(if rolling):

1: Dex

2: Con

3: Wis

Ideal Equipment:

-Shortsword(Levels 1 and 2)

-Rapier(Levels 3+)

-Light or Medium Armor(Levels 1-4)

Level 1: Fighter 1

-Second Wind

-Fighting Style: Unarmed Fighting

Levels 2-6: Monk 1-5

-Unarmored Defense

-Martial Arts


-Dedicated Weapon, this is what lets us switch to a rapier

-Monastic Tradition: Way of Shadow

—Shadow Arts: The main reason we are here is Pass Without Trace. This spell will give us and our whole party a +10 to stealth. Even your party members in armor will be able to pass most stealth checks with this up. With this you’ll want to be sneaking around as much as possible trying to get surprise as much as you can and sometimes you’ll just be able to avoid a fight all together

-Deflect Missiles

-Slow Fall

-ASI or Feat: Piercer +1 Dex. Mainly for the +1 Dex but will boost our damage with our rapier a bit as well

-Extra Attack

-Stunning Strike, ok if the enemy has a low con but you’ll usually be better off using pass without trace and flurry of blows

Levels 7-9: Rogue 1-3

-Expertise: Stealth

-Sneak Attack, an extra 2d6 damage per round if we have advantage or an ally nearby

-Cunning Action: Dash and Disengage as a bonus action will be nice for getting in and out of melee

-Roguish Archetype: Assassin

—Assassinate: This is the main reason we are taking these 3 levels of Rogue. It gives us advantage on all of our attacks if the enemy hasn’t taken a turn yet and if we get surprise all of our attacks are critical hits

Level 10: Fighter 2

-Action Surge

Levels 11-15: Ranger 1-5

-Go with the optional features Favored Foe and Deft Explorer. Favored Foe can be used to get some extra damage in if we’re not already concentrating on something like Pass Without Trace. Deft Explorer will just get us expertise in another skill

-Fighting Style: Dueling


—1st: Absorb Elements, Goodberry

—2nd: Pass Without Trace, Locate Object

-Ranger Conclave: Gloom Stalker

—Dread Ambusher: This is the main reason we’re here, we get an extra attack on the first round and that extra attack does some extra damage as well. We also get a bonus to initiative equal to our Wisdom modifier

—Umbral Sight: We pretty much just have greater invisibility in darkness against creatures with darkvision. This will give us advantage on our attacks and disadvantage on attacks against us

-ASI or Feat: Resilient: Wis. This gives us a +1 to Wis which boosts a lot of different things and we get proficiency in Wis saves which are often the worst ones to fail for us.

-We do get Extra Attack again which is a bit redundant but I think it’s still worth it to get 2nd level spell slots and thus more casts of Pass Without Trace


On the first round of combat you’ll want to up to an enemy that is surprised or that hasn’t taken a turn yet. Attack them 3 times at advantage with your rapier applying sneak attack on the first hit and dealing an extra d8 on the 3rd attack if it hits. You can then action surge and do those same 3 attacks but without the sneak attack. Then use your bonus action and flurry of blows. You’ll want to stow or drop your rapier so that the unarmed strikes do a d8 damage. That’s 8 attacks all with an extra 2d6 each from bugbear as well and if the enemy is surprised all of them will be critical hits if they land.

Nova Damage Vs 19 AC:

Action Surge and Surprised: 271.11

Action Surge and Not Surprised: 156.51

Surprised and No Action Surge: 168.78

Not Surprised and No Action Surge: 98.3

Levels 16-20: 3 Variations

-More levels of monk to get more ki points, Evasion, and a feat

-More levels of fighter to get a subclass and a feat. Echo Knight and Battle Master would both be great options that would boost our nova damage

-The last way I would consider is 2 levels of Genie Warlock. 2 levels in warlock would get us Devil’s Sight which could combo pretty well with the Darkness spell we get from Way of Shadow. This combo can be quite disruptive but may be the right pick in some situations

-All of these variations could be taken at different points throughout the build as well if you want them earlier on

-You’ll probably get at least 1 more feat regardless of which way you go. I’d recommend either Alert to boost your initiative or just a +2 to Dex.

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