Way of Shadow Monk 5e

Review by Sam West, Twitter:@CrierKobold

Way of Shadow is how you bring your secret ninja fantasies to life in D&D. You take the silent infiltration of a rogue, mix it with the monastic focus and dedication to martial arts presented by Monk are left with the tactical assassin capable of breaking in and out and dropping bodies without making a sound.

For only having four features and no expanded resource pool, the Way of Shadow has depth. It suffers from the problems base monk suffers from (namely a constant feeling of not having enough Ki), but past six or seventh level it starts to feel better and better. It's a rare option whose primary feature is unlocked at 6th level as opposed to 3rd, yet has enough going on it doesn't feel too bad with the underwhelming 3rd level feature to dissuade playing it in the lower tiers.

3rd Level: Shadow Arts

With just ki points equal to your level, Shadow Arts 2nd level spell options can feel near impossible to use at 3rd level. You get Darkness, Darkvision, Pass Without Trace, and Silence all at your fingertips for the steep cost 2 ki a pop. Spending over half of your ki for a single 2nd level spell is not a rate I’m eager to pay.

What saves this a bit is Minor Illusion. It's an easy to cast cantrip with great utility at a tier where cantrips still majorly contribute to exploration. Eventually having 6 or more ki will make the cost of a well-timed Pass Without Trace or Darkness feel a lot better. Until then, Minor Illusion is the primary effect unlocked.

What's notable about this list is how it pushes you to specialize in stealth and infiltration. Without any other context from the class, you're set up to drop in unseen and unheard, get the kill without the target making so much as a peep, and dip out without anyone knowing you were ever there. I really wish they were half as cheap, or at least provided a 1st level option that could cost just 1 ki point, but as it stands this is a mediocre starting feature that does get better as you're ki become a bit less taxed.

6th Level: Shadow Step

Way of Shadow comes to life with Shadow Step. Where Shadow Arts give you a bunch of ki based features and Minor Illusion, Shadow Step provides a free bonus action 60-foot teleport so long as you do it from and into dim light or darkness.

From now until the rest of time, you're going to want to know exactly where dim light starts. Snuffing lights suddenly becomes advantageous to set up long-distance travel. Darkvision is a racial must-have, as you really can't afford to waste ki on getting the ability to see where you're going. Not only is this great for getting around dank dungeons and through the depths of the underdark, but it's also a great engagement tool that gets you in a prime position for striking. In this way, it doesn't overlap that much with your Martial Arts or Flurry of Blows; if you are using it to engage when you otherwise couldn't, you're not forgoing any attacks for the teleport.

There are some major constraints of this to keep in mind that heavily reward exploring multiclass solutions, the name one being you can't teleport into spaces you can't see. This makes magical darkness effects unavailable for teleportation. You can't teleport into Darkness you create with Shadow Arts. At least, you can't unless you take a two-level dip into warlock for the Devil's Sight invocation! Additionally, while it might go without saying, needing dim light and darkness to function makes this a void feature in brightly lit environments. If you're a Way of Shadow monk, you're going to want to get the entire party on a nocturnal sleep schedule so you can readily Shadow Step outside. The sun isn't your friend; avoid it like the plague.

11th Level: Cloak of Shadows

The other major component that sets Way of Shadow up for success is Cloak of Shadows, which once again doesn't cost you a single ki point to use. Spending an action to functionally cast an indefinite duration Invisibility on yourself (so long as you're staying in dim light or darkness) can be fantastic.

Not only will you easily get advantage on your first attack roll you make each fight when you come out of the shadows, you can blink around with Shadow Step without ending the effect. This creates a new kind of mini-game where you're finding ways to remotely snuff torches without spells simply to maintain invisibility. You can scout ahead and get all of the locations you can teleport to during a dungeon, and with Darkness at the ready for 2 ki, have a two-action way to literally become invisible from nothing.

Cloak of Shadows is hands down one of my favorite features to have on a monk and the main reason I'm avoiding multiclassing as much as possible up to this point.

17th Level: Opportunist

Opportunist would probably excite me just as much as Cloak of Shadows and Shadow Step if there was something of value between Cloak of Shadows and it. Turns out monks mid-game is pretty trash. Tongue of Sun and Moon and Timeless Body are largely fluff, and Diamond Soul, while powerful, isn't particularly exciting.

If you do commit to the six additional monk levels, getting paid off with what has to be the easiest to provoke reaction attack in the game is a reasonable payoff. Monk's on-hit abilities aren't super high, though. They aren't stacking a bunch of dice on attacks or getting Great Weapon Master damage on hit, making their extra attacks worth a bit less than many other martial builds. A free reaction attack for 1d10+5 anytime an ally strikes is still probably good enough if you want to stick it out, but I think the more powerful options will come from supplementing the core of Way of Shadow with additional stealth and darkness support from outside of the monk class.

All Together

From the PHB, Way of Shadow is my personal favorite monk option. The flexibility Shadow Step and Cloak of Shadows offer when paired with the five spells Shadow Arts provides leaves you with a robust toolkit for all things stealth. Opportunist is a generic, strong 17th level feature, but isn't usually compelling enough to me over picking up supplemental stealth and darkness support like Expertise, Sneak Attack, and Assassinate from Rogue and Devil's Sight and Pact Magic from Warlock.

Multiclassed or not, Way of Shadows is one of Monk's cleaner options to build with and play. You're still a monk, so you still will suffer from all the issues with damage scaling and ki restrictions base monk suffers from, but you are given a ton of great abilities for in and out of combat that can give you a fun character. You're not going to be topping the damage charts or anything, but you'll definitely scratch your ninja fantasy itch if you've got one with this.

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