Rogue Multiclassing Best Practices: D&D 5e Sly Guide

D&D 5e Rogue Multiclassing feature art is “[COMMISSION] Drow Rogue” by cyangorilla. Creative Commons License.
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Welcome to Flutes’ sly guide for Rogue multiclassing character builds. Multiclassing allows you to build interesting concepts for unique characters with outside-the-box specialties. Multiclassing can be useful for roleplaying, so do not make the mistake of thinking this guide is only for min-max-style playstyles. I’m analyzing the Rogue class as both core and secondary within a multiclass build.

Slink Ahead to Another Section:

General Multiclassing Notes
Dipping 1-2 Levels in Rogue
Multiclassing for Any Type of Rogue
Arcane Trickster
Assassin
Inquisitive
Mastermind
Phantom
Scout
Soulknife
Swashbuckler
Thief

My Rogue multiclassing terminology:

• Core Class: The main class for a character which usually holds the majority of level investment for a character.
• Secondary Class: The class that is supplementarily added to the core class.
• Dipping: Multiclassing very few levels into a secondary class.

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General Notes on Rogue Multiclassing

Remember, multiclassing requires minimum ability scores in both new and prior character classes (as described on page 163 of the PHB or page 54 of Eberron RftLW for Artificers). For example, if you are a Cleric and want to multiclass as a Rogue, you’ll need a Wisdom score of 13 or higher and a Dexterity score of 13 or higher. The Multiclassing Proficiencies table is on page 164 of the PHB (or page 54 of Eberron RftLW for Artificers).

You’ll want to perform cost-to-benefit analyses of classes when you consider Rogue multiclassing. Every level in a secondary class is an opportunity cost to your core class. Choosing to multiclass as a core-class Ranger is an easy choice since Rangers don’t typically get worthwhile abilities at higher levels. Other classes like Druid and Fighter have excellent level-twenty abilities, so it hurts to multiclass and forfeit those high-level abilities.

However, most campaigns end by level ten, so it’s not often prudent to plan a character with the assumption of reaching level twenty. Speaking of fun concepts, some of my recommendations made the cut mostly because they are thematically cool or unique to D&D.

Multiclassing Proficiency Info

• Artificer – Intelligence 13: light/medium armor, shields, thieves’ tools, tinker’s tools.
• Barbarian – Strength 13: shields, simple weapons, martial weapons.
• Bard – Charisma 13: light armor, one skill of your choice, one musical instrument of your choice.
• Cleric – Wisdom 13: light armor, medium armor, shields.
• Druid – Wisdom 13: light armor, medium armor, shields (druids will not wear armor or use shields made of metal).
• Fighter – Strength 13 or Dexterity 13: light armor, medium armor, shields, simple weapons, martial weapons.
• Monk – Dexterity 13 and Wisdom 13: simple weapons, shortswords.
• Paladin – Strength 13 and Charisma 13: light armor, medium armor, shields, simple weapons, martial weapons.
• Ranger – Dexterity 13 and Wisdom 13: light armor, medium armor, shields, simple weapons, martial weapons, one skill from the class’s skill list.
• Rogue – Dexterity 13: light armor, one skill from the class’s skill list, thieves’ tools.
• Sorcerer – Charisma 13: no additional proficiencies.
• Warlock – Charisma 13: light armor, simple weapons.
• Wizard – Intelligence 13: no additional proficiencies.

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Dipping 1-2 Levels: Rogue Multiclassing

Before I get into my main Rogue multiclass ideas, I’ll start with some quick ideas for dipping into Rogue. You may not want to get three levels of Rogue to go all the way for a Rogue subclass, but you can still get a good deal with just one or two levels of Rogue. The class abilities that you’d probably multiclass for are Expertise and Cunning Action.

• Level 1: Expertise with two skills to double proficiency bonus, 1d6 Sneak Attack, and the Thieves’ Cant code language.
• Level 2: Cunning Action (bonus action to Dash, Disengage, or Hide).

Several classes can benefit from taking one or two levels in Rogue, particularly classes that have weaker level-twenty capstone abilities that can be passed up. Characters may have less incentive to get to level nineteen or twenty in their core class if the benefits of those levels aren’t insanely good. Aside from that, some characters may want to multiclass as Rogues at lower levels because a campaign isn’t expected to reach level twenty.

Rangers are a good example of a class that won’t care about its high-level abilities, so Rogue multiclassing has much to offer, even if it’s just a dip into Rogue. Spellcasters may also enjoy the added mobility, though they may want to focus on spells to gain escape and mobility options. Rogues aren’t typically included in power-build characters that are highly optimized, but Rogue multiclassing is alright.

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Any Type of Rogue Multiclassing

The next section is for subclass-specific Rogue multiclass combinations. Still, before I get to that, I’ll mention several combinations that are good for any Rogue regardless of the Rogue’s chosen subclass.

Opal has written several articles about her love of Rogue/Fighter characters. In fact, one of her earliest articles is about how she loves to multiclass Rogue with Fighter. I know this is true because I’ve seen her create approximately six characters who were all variations of this concept. The Battle Master Fighter is complimentary of Rogues, making it a strong choice.

Rangers also do well when multiclassed with Rogues. They tend to use Dexterity skills and attacks while also being known for their lone-wolf prowess. The Ranger spell list packs many spells that can benefit a Rogue and their party. Rogues benefit from spells like Fog Cloud (especially with the ‘Blind Fighting’ Fighting Style), Silence, and Pass Without Trace.

Spellcasters who need additional mobility with Cunning Action, and want to bolster their skill proficiencies with Expertise, will find a home with the Rogue. Many spellcasters find it difficult to utilize their bonus actions without casting a spell that uses it. Rogues have no problem using their bonus action nearly every round with Cunning Action. Disengaging as a bonus action will allow a spellcaster to move away from a melee assailant, followed by an action to cast a spell. If the spellcaster’s movement speed is greater than the foe, this could force that foe to use their action to Dash instead of attack as they attempt to catch up. You can achieve this with the Longstrider spell ahead of combat. Wizards and Sorcerers are most likely to make this dip into Rogue.

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Multiclassing by Rogue Subclass

I’ve collected my thoughts by Rogue subclass for your convenience. While I can’t point out every conceivable potent Rogue multiclassing combination, I’ll provide some of my favorites to inspire you! I want to also premise with my disappointment (but agreement) that the combination of Bard’s Jack of All Trades and Rogue’s Reliable Talent features do not work together, so that’s why I won’t mention it further.

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Arcane Trickster Rogue Multiclassing (PHB)

Arcane Trickster Rogue (19) / Arcana Cleric (1) 

With merely one level of Arcana Cleric, you’ll gain proficiency in medium armor and shields (a big boost to your defense), and you’ll choose two Wizard cantrips that become Cleric spells for you. Rogues only need one hand to attack effectively, freeing up the other hand to use a shield. For cantrips, I recommend at least choosing Booming Blade.

Since Rogues only need to make one attack per round, they can cast Booming Blade to deal extra damage in addition to Sneak Attack damage. The melee attack of Booming Blade will not rely on a high Wisdom stat. Booming Blade is handy since you can use your Cunning Action to Disengage and move away from the target, forcing them to move if they want to make a melee attack against you. Flavor the concept as a Rogue informally devoted to a god of magic, resulting in limited (but potent) magical powers.

Arcane Trickster Rogue (9) / School of Enchantment Wizard (11) 

I appreciate this combination of the enchanter’s Split Enchantment feature with the Arcane Trickster’s Magical Ambush feature. When you are hidden from foes, you can cast powerful enchantment spells like Hold Monster and Dominate Person while targets have disadvantage on their saving throws. In my experience, the spells gained by level eleven for an enchanter are the most important (other than Dominate Person as an eighth-level spell), so this character won’t suffer on enchantment utility much. Your enchantment spells will have two targets instead of one, and targets are more likely to fail due to your ambush.

If you cast Hold Monster, you’ll critically hit with your melee attack damage, beefing up your Sneak Attack slices. Enchanters are very powerful, but they rely heavily on foes failing saving throws, making enchanters perfect to pair with the Arcane Trickster’s Magical Ambush. Additionally, the Arcane Trickster may already know enchantment spells due to how trickster spellcasting works, so you’ll be fully loaded and ready to unleash powerful enchantments. This is especially powerful in games with many foes of the humanoid creature type since this character will have Dominate Person as one of its most powerful spells.

Arcane Trickster Rogue (9) / Trickery Domain Cleric (11) 

Like my enchanter combination above, this combination utilizes Magical Ambush to capitalize on powerful debuff spells like Dominate Person or Polymorph (and Modify Memory for the especially creative folks out there). Unlike the enchanter, the Trickery Cleric’s abilities lend well to what Rogues like to do; they can buff Stealth rolls, create illusions of themselves, cast interesting spells that mislead and deceive, and deal extra poison damage.

There is a unique synergy between Invoke Duplicity and Mage Hand Legerdemain that would allow a duplicate to appear real as it seems to pick up items and interact with objects. Still, it’s really just the invisible Mage Hand doing so concurrent to a duplicate’s movements. You’ll need to remain close to the duplicate (120 feet) while remaining hidden and even closer to Mage Hand (30 feet). The duplicate lasts for one minute, so act fast.

Arcane Trickster Rogue (17) / Warlock (3) 

Enrich your Roguish spellcasting in a variety of ways. Choose Pact of the Tome or Pact of the Chain, depending on your preference. You’ll receive two Eldritch Invocations, of which there are several that sound fun for a Rogue to use (depending on your campaign and playstyle). You’ll receive additional spell slots, get access to Eldritch Blast, and choose a patron depending on your desires. I recommend patrons for Fiend, Great Old One, or The Hexblade. The patron that will give you the most value for your multiclass is The Hexblade, one of the most powerful subclasses for multiclassing in the game. Arcane Tricksters don’t need to invest in Intelligence for their spellcasting to be effective; they can choose spells that don’t force saving throws. For this reason, you can afford to invest in Charisma instead.

Arcane Trickster Rogue (17) / Champion Fighter (3)

The Champion will give you Action Surge and the ability to land critical hits on 19s. Cast Find Familiar so your familiar can use the Help action to give you advantage. Action Surge will allow you to attack during your turn with Sneak Attack (assuming your attack qualifies). Your second action will be to Ready an attack that triggers when your familiar uses the Help action. You will have advantage on your reaction attack outside of your turn, allowing you to Sneak Attack a second time in the round. Awesome! You can also learn the Haste spell to the same ends. You can also use Booming Blade instead of your attack in either instance of attacking.

Arcane Trickster Rogue (17) / Battle Master Fighter (3) 

This is always a cool combination. The Riposte maneuver allows for an option to attack during an enemy’s turn with Sneak Attack damage during a round (in addition to Sneak Attack on your own turn). Action Surge allows you to Ready an attack to similarly attack out of turn as a reaction to frequently Sneak Attack. You can Ready action Booming Blade for additional damage. You can use this combination with any Rogue subclass, but a Familiar is helpful to gain advantage on your attacks when it uses the Help action.

Arcane Trickster Rogue (14) / Shadow Monk (6) 

Shadow Monks possess interesting themes and useful mechanics for Rogues, particularly with Shadow Step at level six. The quick teleport grants advantage on a melee attack so the Rogue can use Sneak Attack. This works with pretty much any Rogue.

Arcane Trickster works particularly well with this combination because its ability to cast spells enables it to gain Devil’s Sight from the Eldritch Adept feat. Arcane Tricksters can then combo Devil’s Sight with the Shadow Monk’s Darkness spell. You’ll also get Pass Without Trace and Silence as useful spells.

Arcane Trickster Rogue (14) / Bladesinger Wizard (6) 

Six levels of Bladesinger get you Extra Attack with a cantrip option, meaning you can cast Booming Blade for one of your attacks. You gain additional spells with Wizard level that would normally take you much longer to learn as an Arcane Trickster. You can play with the levels you want to invest in either class, possibly taking two levels of Fighter along the way. Bladesinger also allows you to focus more on your Intelligence if you wish.

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Assassin Rogue Multiclassing (PHB)

Assassin Rogue (17) / Gloom Stalker Ranger (3) 

There is massive synergy with this combination. I love the Assassin’s ability to land critical hits on surprised foes automatically, and it gets even better with the Death Strike feature at level seventeen. The Gloom Stalker Ranger compliments the Assassin in several ways. Umbral Sight grants a buff to the character’s darkvision. More importantly, it makes the Assassin invisible in darkness when hanging around creatures that are confidently relying on their darkvision to see.

The Gloom Stalker is also a natural ambusher like the Assassin. The Dread Ambusher feature will buff the character’s incredible Assassinate attacks when ambushing a target. Movement speed is also increased by Dread Ambusher, and it also grants a bonus to initiative rolls equal to the character’s Wisdom modifier. I am giddy to see how much synergy exists here. If there is a Grave Cleric in the party, you’re gonna have a good time.

Assassin Rogue (17) / College of Glamour Bard (3) 

One of the worst parts of being an Assassin is dealing with the lackluster subclass features Infiltration Expertise and Infiltrator. They don’t pay off as much as I’d like them to, and their benefits can be achieved in other ways. We should make the most of those features, and the Glamour Bard has a unique way to do so. I recommend you create a false identity as an entertainer. The persona gets you in front of powerful people during a performance. During your act, you can attempt the subtle Enthralling Performance ability of the Glamour Bard.

You’ll be able to charm specific targets in a room with a bit of time investment without visible spellcasting or revealing yourself. You can use this charm effect to gain people’s trust so you can find out where your mark is. If you wish to invest three additional levels into Bard, you’ll gain the Mantle of Majesty feature; with it, you can charm someone specifically and get them alone to cast Command on them over and over again as you slay or steal from them. I imagine this like an exotic dancer who takes advantage of the one-on-one situations that can result afterward with interested parties. You also get extra Expertise from three Bard levels.

Assassin Rogue (17) / Grave Domain Cleric (3) 

One of my first articles on this site was about this multiclass combination, the Assassin of the Grave (in hindsight, maybe that title is redundant). You really only need two levels of Grave Cleric to gain the Channel Divinity: Path to the Grave. This will allow you to make a target vulnerable to your damage (that means they’ll take double damage). You’ll be able to achieve damage for one attack upwards of 500 damage! Take a third Cleric level for second-level spells like Enhance Ability, Silence, Augury, and Find Traps.

Assassin Rogue (17) / The Hexblade Warlock (3) 

This Assassin Rogue leans heavily into the social skill checks like Deception and Persuasion. A good assassin will find a way to invest in Charisma for social skill checks, but it gets crowded sharing stats with Dexterity and Constitution. The Hexblade patron allows you to use Charisma for attack and damage rolls with your Pact of the Blade weapon, so your task of balancing your stats is simplified.

The Pact of the Blade also grants you the ability to summon your weapon, so you can go into a social situation unarmed. When the moment is right, you can unleash your pact weapon and deal massive damage to a surprised enemy. Put thirteen or fourteen points into Dexterity and Constitution, and go full force into Charisma with this combination.

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Inquisitive Rogue Multiclassing (XGtE)

Inquisitive Rogue (19) / Arcana Cleric (1) 

I previously recommended this multiclass for the Arcane Trickster. Still, Inquisitive Rogues have more incentive to invest in Wisdom to use Booming Blade more effectively as a Cleric spell while dealing Sneak Attack damage. You’ll also gain the medium armor and shield proficiencies to boost your AC.

Inquisitive Rogue (19) / War Cleric (1)

The greatest wars are won with mind games, and this character knows it. Investing in Wisdom will help the Inquisitive Rogue due to its reliance on perception and insight checks. You can use a shield and heavy armor, so what about the usual off-hand attack as a bonus action? War Priest covers that. Clerics also get useful level-one spells. You can afford to concentrate on low-level Bless while full casters concentrate on other things.

If you’re going to rely on stealth, consider ditching the heavy armor for light or medium armor; otherwise, keep it around. You’ll also be able to use a longbow since you’ll have martial weapon proficiency.

Inquisitive Rogue (18) / Stars Druid (2)

The Inquisitive Rogue thrives on being able to perceive and deduce. The Stars Druid has a tool to help with those investigative skill checks. Dragon Starry Form provides a minimum of ten Intelligence and Wisdom checks. This helps the Inquisitive Rogue to roll reliably for these few skill checks at far sooner levels than the Rogue with Reliable Talent. It’s cool to imagine the Rogue going into a starry mode when investigating a scene, but it also helps with Insightful Fighting during combat.

Inquisitive Rogue (17) / Fey Wanderer Ranger (3)

This combination makes a useful face of the party because of the Fey Wanderer’s Otherworldly Glamour feature. It allows your character to add its Wisdom modifier to Charisma skill checks and gain proficiency in one social skill. Since the Inquisitive Rogue uses Wisdom for several of its abilities, it can double up on Wisdom’s usefulness with levels of Fey Wanderer. Ranger spellcasting will be useful for your investigations, especially Charm Person from the Fey Wanderer Magic feature.

In combat, this combination can play into the fey influence by making Insightful Fighting into a trickster’s way of reading movements, feinting attacks, and otherwise tricking enemies into disadvantageous battle stances. I imagine this character narratively pulling an enemy’s hat over their eyes to gain Sneak Attack.

Inquisitive Rogue (17) / Monster Slayer Ranger (3)

Archetypal hunters of the occult and alien must be perceptive enough to pierce and expose beguiling facades. The Monster Hunter has Hunter’s Sense at level three to complement the investigative powers of the Inquisitive Rogue. In addition to the mundane investigative skills of the Rogue, the Monster Hunter Ranger will perceive a supernatural creature’s strengths and weaknesses.

Inquisitive Rogue (18) / Genie Warlock (2)

This idea came from YouTube commenter Brian Hatchett: “Hex is strong on an Inquisitive, targeting Charisma for the Insightful Fighting ability and then enjoying the extra damage too. Make it a Genie Warlock and add your PB in damage each turn. Also, having the Genie’s Respite gives you a place to safely store clues and files.”

I love this idea, especially making the genie’s bottle into a conspiracy theorist’s cluttered room.

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Mastermind Rogue Multiclassing (XGtE)

Mastermind Rogue (8) / Battle Master Fighter (12)

The battlefield commander! This combination aims to have the Mastermind archetype dialed up with Superiority Dice and Maneuvers like Maneuvering Attack. You’ll use your bonus action from up to thirty feet away to use the Help action, supporting your allies. The 8/12 split is great for getting essential class features and ASI’s.

Mastermind Rogue (3) / Divination Wizard (17)

This one was suggested on YouTube, and I thought it sounded like a fun, squirrely support caster. You can flavor Mastermind’s special Help bonus action as a quick look into the future that allows you to help your allies. It reminds me of that Nicholas Cage movie Next where he can always see a few moments into the future.

Instead, you can focus on the Rogue levels and re-flavor Portent as masterful planning instead of divination magic.

Mastermind Rogue (17) / Rune Knight Fighter (3)

Fighters make great Rogue multiclasses, and the Rune Knight Fighter has interesting features that complement the Mastermind Rogue. The Cloud Rune allows the Mastermind to become a tricky battlefield controller by redirecting an attack to magically strike another creature. Basic Fighter features like Action Surge, Second Wind, and a choice of a Fighting Style can enhance the Rogue’s abilities to bolster its defenses or enhance its damage output.

You can narrate this character as being a master of tactics who learned to master battle through games of wit with rune carvers and giants.

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Phantom Rogue Multiclassing (TCoE)

Totem Barbarian (11) / Phantom Rogue (9)

You linger strangely in the realm of the living while you enter a spiritual rage that tethers you to mortality. You are in touch with the spirits of the dead, creating totems and trinkets that empower you with voodoo magic. While a Token of the Departed trinket is on your person, you’ll have advantage on Constitution and death saving throws; these trinkets empower your Relentless Rage saving throws to keep you among the living.

With the Bear Totem at level three, you’ll resist all damage types except psychic damage. After you resist damage, you can use your reaction with the Rogue’s Uncanny Dodge to halve the remaining damage. You effectively reduce incoming damage from one attack per round by 75%.

You can wield a finesse weapon while using your Strength. You’ll gain Expertise in Athletics, so you successfully grapple with enemies reliably. You’ll have advantage on grapple checks while raging. Reckless Attack enables advantage on Strength-based melee attacks to gain Sneak Attack damage.

Echo Knight (3) / Phantom Rogue (17)

Echo Knights can be flavored as ghostly manifestations of the Rogue! Use Manifest Echo to create a ghostly version of yourself that can deal Sneak Attack damage. This is a fun way to play a melee-based Rogue. As you level up in either class, the new abilities will continue to feed into the ghostly theme.

The level split is flexible, so do what you want with it. Thank you to Cleric Corner for this idea!

Horizon Walker Ranger (3-11) / Phantom Rogue (9-17)

The levels of this multiclass concept are flexible. This combination’s build will depend on what you’re prioritizing for features. These subclasses go together in a neat way. I like their themes, and the Horizon Walker can be flavored to be an extension of the Phantom Rogue. The Phantom Rogue doesn’t need to use its bonus action all the time, so it can utilize the Planar Warrior damage. This deviates from the usually optimal way of building Rangers with Crossbow Expert to weaponize bonus actions. This won’t out-damage those builds, but it’s an alternative with fun mechanics.

Both subclasses have an ethereal-based feature, so decide which one you want to go for (if any). I’d personally be tempted to go eleven levels of Horizon Walker Ranger so I can blink around the battlefield between attacks. It’s not optimal to spread out attacks, but this is so cool to visualize.

Twilight Cleric (1) / Phantom Rogue (19)

One level of Twilight Cleric gets you so much, and I believe the theme fits well with these two subclasses. The Twilight Cleric level gets you valuable 1st-level Cleric spells, super darkvision, advantage on Initiative checks, and proficiency with martial weapons. You might be interested in martial weapons like heavy crossbows or longbows. You can take another level of Twilight Cleric to get its Channel Divinity to help your party’s survivability in a tough fight.

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Scout Rogue Multiclassing (XGtE)

Scout Rogue (17) / Path of the Totem Warrior Barbarian (3) 

This concept functions as a wilderness survivor and duelist. First, Rogues don’t need to invest in Dexterity. In fact, they can use Strength while still getting Sneak Attack damage because they only need to use finesse weapons; Sneak Attack only requires a finesse weapon to be used. Invest in a thirteen or fourteen for Dexterity so you can multiclass, but invest primarily in Strength and Constitution.

Thanks to your Barbarian levels, you’ll be able to Rage to resist damage. You’ll essentially reduce incoming damage from a single attack by 75% when you use Uncanny Dodge.

You’ll also have Reckless Attack (only available with Strength-based attacks), affording you advantage on attacks. You gain Sneak Attack even if an ally is not near your target because of Reckless Attack (if you attack with a finesse weapon and with your Strength). Unarmored Defense and Danger Sense are great, too. You’ll likely pass Dexterity saving throws to take no damage from AOE effects like Fireball, thanks to your Evasion ability.

You’ll learn Beast Sense and Speak with Animals as rituals. You can speak with beasts to learn about the lay of the land and the creatures that dwell within. Expertise will allow you to be a grappling master by picking Athletics; while Raging, you’ll have advantage on Strength checks like a grapple, add double your proficiency bonus to the roll, and your minimum dice roll will be a ten once you get Reliable Talent. Good luck to anyone attempting to resist or break that grapple.

Scout Rogue (14 or 19) / Twilight Cleric (1 or 6)

As one of my favored subclasses, the Scout Rogue would be more fun to play if it had 300 feet of darkvision. If you go with the six levels of Cleric, you’ll get Steps of Night to gain flight while in darkness. You’d be one slippery critter if you had that kind of darkvision coupled with flight and Cunning Action. Vigilant Blessing makes your allies keen on an Initiative roll so they can keep up with you. You can use it on yourself until level thirteen of Rogue to gain Ambush Master. The Channel Divinity: Twilight Sanctuary feature supports allies without concentrating or relying on a high DC.

Gloom Stalker Ranger (12) / Scout Rogue (8)

This combination allows you to get the best class and subclass features from the Gloom Stalker while complimenting the build with Rogue levels. The Scout Rogue is particularly thematic for playing as an archer, and Rangers excel with the Crossbow Expert feat. The Rogue boosts your damage with Sneak Attack and gives you evasive, defensive options. This prescribed level split allows you to still get five feats.

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Soulknife Rogue Multiclassing (TCoE)

Soulknife Rogue (14) / Genie Warlock (6)

Without requiring concentration or spell slots to do so, you’ll gain invisibility and a flying speed so you can be a stealth jet. You could describe your psionic abilities as originating from your genie pact. You’ll gain Invocations to customize your Rogue further, gaining abilities that can be flavored to be based on your psychic powers.

Notable Invocations are Misty Visions (cast Silent Image at will), Eldritch Sight (cast Detect Magic at will), Ghostly Gaze (x-ray vision with concentration), Trickster’s Escape (cast Freedom of Movement without a spell slot), and Gift of the Depths (cast Water Breathing without expending a spell slot, and learn to swim).

Soulknife Rogue (14) / Twilight Cleric (6)

This combination can use the powerful Channel Divinity: Twilight Sanctuary, allowing you to protect your allies’ minds and hitpoints as you invisibly float around with your dim sanctuary. Like my prior suggestion with the Genie Warlock, this combination allows you to invisibly fly without spells or concentration to do so, using Steps of Night. I recommend narrating your psionic abilities as originating from your own presence between worlds, like a constant state of twilight causing you to have unnatural abilities.

Soulknife Rogue (9) / Swarmkeeper Ranger (11)

Reflavoring the psychic abilities of the Soulknife Rogue to fit the swarm theme of the Swarmkeeper Ranger is straightforward narratively and useful mechanically. Your swarm can be summoned in the form of a blade or other tool to help you in a moment of need. Going to level eleven as a Swarmkeeper allows you to gain flight and enhance your swarm’s attack enhancements. You don’t need Swarming Dispersal since the Rogue side of this character will have Uncanny Dodge for its defensive reaction. Mighty Swarm allows you to knock an enemy prone so you can gain advantage on a second attack for Sneak Attack damage (since you’ll have Extra Attack).

As I mentioned earlier, Ranger spells are game-changers for Rogues: Pass without Trace, Silence, and Fog Cloud will help Rogues do what they do best. Gaseous Form from the Swarmkeeper Magic will assist in escapes and infiltrations, and you can describe it like you’re a Naruto character or Yiga Clan member disappearing in a puff of smoke. Web is another amazing spell from Swarmkeeper Magic. You get a plethora of utility from this combination.

Horizon Walker Ranger (16) / Soulknife Rogue (4)

Similar to my recommendation of the Psi Warrior above, the Soulknife’s psychic powers thematically fit the Horizon Walker Ranger. The Soulknife allows you to create telepathic walkie-talkies with your allies and bolster your skill checks. For added damage, you can manifest psychic blades that pair with your Planar Warrior and Sneak Attack features. I kinda picture this combination as Kabuto from Naruto, who could sever muscles and tendons without breaking the skin of his enemies.

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Swashbuckler Rogue Multiclassing (XGtE)

Swashbuckler Rogue (18) / The Hexblade Warlock (2) 

One of the challenges of being a Swashbuckler is trying to beef up your Charisma in addition to other Rogue stats like Dexterity. With just one level in Warlock with The Hexblade patron, you’ll be able to attack with your finesse weapon using Charisma instead of Dexterity or Strength for your weapon’s attack and damage rolls.

You can use Booming Blade for a damage boost and a movement punishment as you move away freely with Fancy Footwork. The Hexblade also gives you medium armor and shield proficiencies so you can focus on Charisma without sacrificing defense.

Totem Barbarian (15) / Swashbuckler Rogue (5)

You are a master duelist and showman; you’re used to wrestling with mighty beasts and playing hide and seek with agile creatures of the wilderness. You resist damage with Rage and then halve the resisted damage by reacting with Uncanny Dodge. You Fancy Footwork gives you a portion of the Mobile feat, allowing you to strike then move away. Your Unarmored Movement will make you faster than most opponents, making them unable to catch up to you without using their action to Dash. You can kite melee foes in this way, dashing about and even hiding with your Cunning Action bonus action. Use a Rapier to get Sneak Attack, but focus on Strength so you can get Rage damage.

Battlemaster Fighter (5) / Swashbuckler Rogue (15)

This character is dangerous to approach, punishing enemies who dare to duel. Get two shots at Sneak Attack since you’ll have Extra Attack. Use a shield and rapier with the Duelist Fighting Style. Fancy Footwork allows you to strike opponents and then move away for a melee kiting style. Your Maneuvers can be used to react for Sneak Attack on other creatures’ turns, securing the coveted x2 Sneak Attack per round. You can also bolster your defenses in a pinch.

Rogue Swashbuckler (10) / Artificer Artillerist (10)

This invention is appropriately named the “Swashgunner” by Opal in her seafaring article.

Realistically, we tend to argue that a player should only take one to three levels of a secondary class to gain armor and skill proficiencies, with maybe a few top-class features. However, sometimes it is exceptionally more fun to build a multiclass for the gimmick and utility. This is one of those builds.

Start as a Rogue Swashbuckler for an initial four skills and weapon proficiencies that indulge Sneak Attack. With the Artificer multiclass, this build focuses less on spellcasting and more on accentuating the Swashbuckler abilities through buffs, utility spells, and an arcane cannon.

At level 9, Artificers can cast Water Walk, even as a ritual, which would preserve their spell slot. Take the battle away from your precious ship, or sabotage the vessels of your enemies stealthily. Combine this with damage from one’s own personal cannon on board, and you’ve got yourself a savvy, tinkering (and repairing!) pirate with unexpected utility. 

With skills in woodcarver’s and other artisan tools, the Artificer addition brings a myriad of magic items (of which you can attune to four and craft in a quarter the time and half the cost) and powerful complimentary infusions. See our articles on crafting magic items for more inspiration.

To really milk this multiclass, a player should focus on high Dexterity and Charisma, even though Artificers shine with Intelligence. Be more of a Swashbuckler in heart than a tinkerer.

Hunter Ranger (3) / Swashbuckler Ranger (17)

The Swashbuckler excels at one-on-one combat, and the Hunter has the tools to enhance this specialty. The Hunter’s Giant Killer feature makes it easy for the Swashbuckler to attack as a reaction and deal Sneak Attack damage on an enemy’s turn. It only works against big boys, but it’s a useful tool. Ranger spells are also excellent for Rogues. Goodberry and Pass without Trace, for example, are premium spells for a Swashbuckler and their party.

Swashbuckler Rogue (10) / Cavalier Fighter (10)

You can play a pirate Bugbear with this concept and have some fun. Bugbears add five feet to the reach of their melee attacks, which couples interestingly with the Cavalier’s Hold the Line feature. You won’t need a polearm to cover a larger area with your melee range, allowing you to attack with a finesse weapon to use Sneak Attack as a reaction. You can have some fun with a melee combination like this.

Swashbuckler Rogue (3-5) / Swords Bard (15-17)

This combination gives you interesting ways to boost your AC while feeding into the swashbuckling theme. You could go for more levels of Rogue if that’s your preferred class, but going for more spells feels right, especially since you can gain Extra Attack at level six with the College of Swords (that’s probably comparable to the Swashbuckler’s level-seventeen feature).

Suggested by MJP3 in the comments!

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Thief Rogue Multiclassing (PHB)

Arcana Cleric (1) / Thief Rogue (19) 

Thief Rogues enjoy getting close to enemies to use Fast Hands. One fun trick is to use Fast Hands to throw oil at an enemy as an improvised weapon, and oil will cause them to take +5 damage from fire damage. With the Arcana Cleric, you can learn Green-Flame Blade as a cantrip to trigger the fire damage on the same turn. Alternatively, you could be a High Elf for your race to gain the cantrip, but Arcana will do well for you otherwise. You’ll also gain medium armor and shield proficiencies, and Cleric spellcasting.

Thief Rogue (17) / Gloom Stalker Ranger (3)

I know I already suggested this for the Assassin Rogue, but it’s just so good for the Thief too! When I play a Thief, I want my presence to be completely hidden. The Gloom Stalker can literally make this character invisible in the dark to creatures with darkvision, meaning you can perform heists with ease on monsters that would normally be deadly encounters. Your initiative rolls will be boosted too. Your character may also be relieved to receive new or buffed darkvision from the Gloom Stalker. The Ranger’s spell list ain’t bad either for heist purposes, such as Longstrider, Fog Cloud, Jump, Detect Magic, and Alarm. Hunter’s Mark will also be useful if you’re tracking down someone you need to rob.

Thief Rogue (17) / College of Glamour Bard (3) 

I am once again copying my recommendation for the Assassin Rogue. Use the Glamour Bard’s Enthralling Performance ability to gain people’s trust without drawing suspicion. This will open doors to you that would normally be hidden or impassable, allowing you to find important stolen items, magic items worth stealing, kidnapped children, or any other noun that you seek. Networking is important! If you want six levels of Bard, you’ll gain the Mantle of Majesty feature to seduce people and take them out back to rob them as you command them to empty their pockets. You also get extra Expertise from three levels of Bard.

Thief Rogue (17) / Circle of the Moon Druid (3) 

The ability to shapeshift into beasts can lend well to a cat burglar. Transform into an indigenous beast to go incognito. Your equipment can transform with you too. If you find the object you wish to steal, return to your normal form, nab it, then shapeshift again to have it disappear into your beast form with the rest of your things. You’ll also impersonate pets of powerful people, getting close to them to steal their prized possessions. Go to level three in Druid to gain the Druid’s level-two spells, especially Locate Object and Pass without Trace.

Thief Rogue (17) / Battle Master Fighter (3)

This combination primarily serves the purpose of using the Disarming Strike maneuver with the Fast Hands ability. You’ll disarm the foe of something important they’re holding, then quickly swipe it from the ground as a bonus action. You’ll also have Action Surge in a pinch.

Draconic Bloodline Sorcerer (17) / Thief Rogue (3) 

Use Fash Hands to coat a creature in oil as a bonus action improvised attack (oil (flask) adventuring gear). Hitting the creature will cover it in oil for one minute, and each instance of fire damage dealt to it will be boosted by five. Cast Scorching Ray to potentially deal fifteen extra fire damage from the oil if all your rays hit. Elemental Affinity will add your Charisma modifier to the damage once, potentially adding five fire damage.

You can create a potent fire blaster with this combination, and Cunning Action is always great for getting into advantageous positions or avoiding getting surrounded. Use any Sorcerer for this combination, but the Elemental Affinity of the Draconic Sorcerer made it stick out for fire damage.

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Conclusion

The Rogue is a versatile class, though its subclasses are hit and miss; therefore, I didn’t imagine many exciting Rogue multiclassing options for Roguish Archetypes like the Mastermind and Inquisitive. They’re not bad subclasses, but they fit into a niche that doesn’t mesh well with any combination I’ve imagined. There are viable multiclass combinations, naturally, but nothing with intense synergy worth mentioning.

What Rogue multiclassing recommendations did you like? What are your favorite Rogue multiclassing options? Comment below in Thieves’ Cant, and I might add your own recommendations to the article.

Thanks for reading! Good luck with your roguish tomfoolery.