Monk / RogueMulticlass Build Guide — D&D 5e

Everything the rogue dip offers runs on Dexterity, which the monk was already maxing. Expertise at Rogue 1 doubles proficiency on two skills — Stealth and Acrobatics are the obvious picks — something the monk class never provides despite being a Dexterity-first martial. One level also adds Sneak Attack (1d6), and because a monk’s unarmed strike is not a finesse weapon, you use a shortsword (which is both a monk weapon and finesse) to qualify. The die is small, but it fires every turn with an adjacent ally.

Rogue 2 adds Cunning Action: Dash, Disengage or Hide as a bonus action. This directly competes with the monk’s Flurry of Blows and Martial Arts bonus strike, but the difference is resource cost. Step of the Wind costs a ki point; Cunning Action is free. On turns where you need to reposition or escape rather than deal damage, Cunning Action saves the ki for Stunning Strike on the turn that matters.

The cost is exactly what you expect: one or two levels of delayed ki pool growth, martial arts die progression, and access to later monk features. Diamond Soul at monk 14 becomes 15 or 16. The trade is worth it when your table values skills and stealth alongside combat — the Way of Shadow monk with Expertise in Stealth and a free bonus-action Hide is the definitive infiltrator build.

Ability priority: DEX → WIS → CON — Dexterity is attacks, damage, Sneak Attack qualifying weapon (shortsword), and half your AC. Wisdom is the other half of AC and your Stunning Strike DC. Constitution keeps a d8 hit die alive. No new stat requirement — Rogue multiclass needs DEX 13, which the monk exceeds by default.