Rogue Monk Multiclass 5e: What Most People Get Wrong

You've probably seen the "Ninja" build floating around forums for years. It sounds incredible on paper—the ultimate shadow-stepping, back-stabbing machine that moves 60 feet in a blink and deletes a wizard before they can even reach for their component pouch. Honestly, most people dive into a rogue monk multiclass 5e build expecting to be a god of the battlefield, only to find themselves starved for Ki points and struggling to keep up with the pure Fighter who's just hitting things three times.

It’s a tricky balance. You're trying to mash together two of the most "resource-hungry" classes in Dungeons & Dragons.

But if you do it right? You become the most annoying person at the table for your DM. You're basically untouchable.

Why the Rogue Monk Multiclass 5e Synergizes (And Why It Clashes)

The core appeal here is the "Action Economy." Both classes love their bonus actions. Monks use them for Martial Arts, Flurry of Blows, and Patient Defense. Rogues use them for Cunning Action (Dash, Disengage, Hide).

Here is the thing: a Monk can already Dash or Disengage as a bonus action by spending a Ki point (Step of the Wind). By taking two levels of Rogue, you get those same features for free. Forever. No Ki required. That alone saves your limited Ki pool for the stuff that actually matters, like Stunning Strike.

However, you've got to watch out for the "Sneak Attack trap." You can only trigger Sneak Attack with a finesse or ranged weapon. Your fists, while they use Dexterity, are technically "unarmed strikes" and not weapons. To get that extra d6 damage, you need to be holding a dagger or a shortsword.

The MAD Problem

Both classes are MAD—Multiple Ability Score Dependent.

• Dexterity: Your attacks, AC, and initiative. You need this at 20.
• Wisdom: Your Monk AC and your Stunning Strike save DC.
• Constitution: You’re a d8 hit-die class. If you don't have at least a 14 here, you're going to have a very short career.

If you try to prioritize everything, you end up mediocre at all of it. Most veteran players recommend pushing Dex to the max and letting Wisdom sit at 16 unless you’re heavily relying on those Monk stuns.

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The "Actually a Ninja" Build: Shadow Monk and Assassin

This is the classic. If you want to play a character that feels like they stepped out of a Sekiro or Tenchu game, this is your path.

The Level Split: Most people find the "sweet spot" at Monk 6 / Rogue 3.

Why Monk 6? Shadow Step. You get a 60-foot teleport as a bonus action whenever you're in dim light or darkness. It also gives you advantage on your next melee attack. In D&D 5e, advantage is the easiest way to trigger Sneak Attack.

Why Rogue 3? The Assassin subclass. If you can surprise an enemy, every hit you land is an automatic critical hit. Imagine teleporting behind a guard, unloading two shortsword attacks, and doubling all those Sneak Attack and Martial Arts dice. It’s a "Nova" build—high burst damage right at the start of the fight.

A quick reality check: Assassin relies heavily on the "Surprised" condition. Many DMs play this strictly, and if your party’s Paladin is clanking around in plate armor, you’re rarely going to get that surprise round. If your group isn't the "stealthy" type, you might find the Assassin features sitting on your character sheet gathering dust.

The "Skirmisher" Alternative: Swashbuckler and Open Hand

If the shadow-ninja thing feels too edgy, look at the Swashbuckler (Rogue) paired with Way of the Open Hand (Monk).

Swashbucklers get "Fancy Footwork." Basically, if you make a melee attack against a creature, they can't make opportunity attacks against you for the rest of your turn. You don't even have to hit them. You just have to try.

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This turns the rogue monk multiclass 5e into a "hit-and-run" specialist.

1. Run in.
2. Punch the big scary Giant.
3. Use Open Hand Technique to knock them prone or push them 15 feet away.
4. Walk away without using your bonus action to Disengage.
5. Use that bonus action to Dash even further or Hide.

You become a ghost. The enemies spend their turns just trying to reach you while you're already 80 feet away, laughing.

Crucial Breakpoints: When to Jump Ship

The biggest mistake is multiclassing too early. If you start as a Rogue 1/Monk 1, you're going to feel weak. You won't have "Extra Attack" (which Monks get at level 5) until you're a level 6 character.

Trust me, being level 5 and only attacking once while the rest of your party is swinging twice or casting Fireball feels terrible.

The Golden Rule: Get to Monk 5 first.
Extra Attack is the single biggest power spike for any martial character. Once you have that and Stunning Strike, then you dip into Rogue for those sweet expertise skills and Cunning Action.

Expertise: The Secret Sauce

Don't sleep on the Rogue’s Expertise. Most people put it into Stealth, which makes sense. But putting Expertise into Athletics on a Monk? That's a pro move. Even with a low Strength score, having a massive bonus to Athletics makes you a grappling god. You can run up walls, grab a wizard, and drag them 40 feet into the air before dropping them.

Addressing the Evasion Redundancy

One annoying thing about the rogue monk multiclass 5e is that both classes get "Evasion" at level 7. This ability lets you take zero damage on a successful Dex save instead of half.

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If you go Monk 7 and Rogue 7, you've essentially "wasted" a high-level feature. It doesn't stack. You don't get "double evasion."

Because of this, most optimized builds stop one class at level 6.

• The Monk-Heavy Path: Monk 17 / Rogue 3 (Classic, gets you the Monk's 17th level subclass feature).
• The Rogue-Heavy Path: Rogue 14 / Monk 6 (Gives you massive Sneak Attack damage and the Shadow teleport).

Equipment and Weapons

You're a Monk, so you aren't wearing armor. But as a Rogue, you have access to more weapons.

With the optional "Dedicated Weapon" rule from Tasha’s Cauldron of Everything, you can actually turn any simple or martial weapon you're proficient with into a "Monk Weapon," provided it's not heavy or special. Since Rogues give you proficiency in things like rapiers or longswords (if you're an Elf), you can suddenly be a Monk swinging a d8 weapon instead of a d4 or d6.

Just remember: Sneak Attack requires a Finesse weapon. A quarterstaff is a Monk weapon, but it isn't Finesse. You can't sneak attack with a stick. Use a shortsword or a rapier.

Practical Steps for Your Build

If you're sitting at a table tomorrow and want to start this journey, keep these steps in mind:

1. Start with Monk: You get the saves you want (Strength/Dexterity) and the basic kit.
2. Rush to Level 5: Do not multiclass until you have Extra Attack. I cannot stress this enough.
3. Take 1 Level of Rogue: This gets you Expertise and 1d6 Sneak Attack. It's a massive utility boost immediately.
4. Evaluate Your Ki: Are you constantly running out? If yes, take that 2nd level of Rogue for Cunning Action. If you're doing fine, stay Monk until level 6 for your subclass feature.
5. Pick Your Ending: Decide if you want to be a high-damage dealer (more Rogue levels) or a battlefield controller (more Monk levels for more Ki and Stunning Strikes).

This multiclass isn't about being the "strongest" in terms of raw math. It's about being the most versatile. You can scout, you can pick locks, you can stun bosses, and you can disappear into the shadows. You're the Swiss Army Knife of the party—just make sure you don't forget to keep your shortsword sharp.

Next Steps for Your Character

• Check if your DM allows the Dedicated Weapon optional rule from Tasha's; it changes your weapon options significantly.
• Map out your level progression to ensure you don't hit the "Evasion" redundancy at level 14 (7/7 split).
• Coordinate with your party’s "face" character to see if you can reliably get Surprise rounds if you're planning on the Assassin route.