Ultimate Guide to Rogues in D&D 5e

Guide by Sam West, Twitter:@CrierKobold

You sneak. You stab. You steal. You do the rogue thing. 5th edition rogues are all about consistency- from high damage numbers you can turn on round after round to skill expertise that will define you as the character to do the stealth missions, rogue is built without resources and a myriad of options out the gate for spicy combat decisions. It doesn’t grow much from there outside its subclass decision, meaning you’re going to need to love Cunning Action and Sneak Attack to have a great time in combat as a rogue. Sneak Attack gates a lot of feats’ potential power like Sharpshooter, as you’re able to access its benefits once a round typically from your attack limitations. This leads to rogues feeling worse off than rangers and fighters in the mid to upper tiers in weapon-based combat.

Additionally, you’ll need to come to terms with the class's upper-tier lackluster utility, as most other classes have some amount of magic that can reshape reality and teleport between worlds while you’re still just getting a +10 or +12 to checks you make to hide. That being said, especially in the early tiers, rogues can still be a delightful and rewarding time with ample opportunity to shine.

One other core element that gets me eager to play the class is its status as an “expert” instead of as a thief or assassin. Sneak Attack simply says one attack you make a turn is empowered, and Expertise isn’t limited to any specific abilities. This “flavor flexibility” gives you room to transform the aesthetic of rogue to fit a wide variety of fantasies, from the student of war studying history and athletics to a battlefield surgeon using their medical expertise to deliver precise blows to the creature’s vitals. Sure, you absolutely can stick with the classic sneaky, thieving archetype the class is known for, but with some imagination, the class can represent a massive array of character types.

Using This Guide

Rogue's core complexity comes down to three features you get at levels in the first three levels: Sneak Attack, Cunning Action, and your Roguish Archetype. After that, you’re building a character out with an Ability Score Improvement or feat every other level and a series of passive features that’ll empower you numerically but not offer you new ways to interface with the world.

If you’re making a rogue for the first time and want to know the basics, the first few sections detailing your equipment proficiencies, Sneak Attack, Cunning Action, and Subclass Selection will give you all the information you’ll need to readily churn out great damage early on with set expectations for growing into the mid and upper tiers.

Alternatively, if you’re playing a rogue and finding elements of your character lackluster in the mid to upper tiers, the core elements I’d look at are your subclass and feat selections or check in on some rules and tactical advice presented in the Sneak Attack and Cunning Action sections. There aren’t a lot of other elements you’re customizing for the class unlike the spellcasting classes; most of your features are locked in by 3rd level, with few decisions left to adjust your character's impact level to level.

Rogue 101

Characters starting as rogue have a few major things going for them: they get two baller features at 1st level, four class skills instead of the regular two, a free proficiency with the most relevant tool kit in the game, and proficiency with shortbows, hand crossbows, rapiers, and shortswords.

Ability Score Assignments

All this together makes rogue a class that is easy to assign ability scores to: high Dexterity, then whatever other ability scores you want your skills to highlight most.

Starting Proficiencies and Equipment

As a rogue, you’re going to get very familiar with two weapons typically: a ranged d6 weapon (typically a shortbow or hand crossbow) and a finesse melee d8 or two finesse melee d6 weapons (rapier or a pair of shortswords). These are basically the best weapons you have access to, as they all interact with your main damaging feature: Sneak Attack.

A way to upgrade most rogues would be to get access to martial weapon proficiency to upgrade into heavy crossbows for a better range and larger damage die.

Daggers are a flexible option; it can be nice to have one or two of them. Sometimes you run out of arrows or need to hold something in one hand while attacking; daggers are a means of getting Sneak Attack damage at a short range while flexibly also working as extra attack options if you’re not spending your bonus action. Compared to shortswords, your knocking the on-hit damage die own one tier in exchange for the thrown property. Because the only cost to your character is carrying capacity and gold, both are reasonable to have at the ready.

Rogue AC. With just light armor proficiency, you’re going to also have an easy time calculating your AC. If you can budget it from your starting gold, Studded Leather is literally as good as you’re going to be able to get until magic armor comes into play, setting your AC at 12 your Dexterity modifier. Most characters start with a Dexterity of 16 or 17, making your starting AC usually 15.

Beyond the regular weapons and armor, rogues also have to pick up Thieves’ Tools to interact with locks and other thievery-based events.

That’s kind of it, though. There isn’t a lot of weapon diversity in Rogue, and most of the new directions you can look toward are going to come from your DM and their distribution of magic items.

1st Level: Sneak Attack, Expertise, and Thieve’s Cant

Sneak Attack

Where rangers and fighters make multiple attacks with their weapons, rogues make one, and hit harder thanks to Sneak Attack. When you get it and every two levels after that, you get a bonus d6 once per turn you can add to a finesse or ranged weapon attack’s damage roll if you have advantage on the attack, or if you have an enemy of the hit creature within 5 feet of it. It doesn’t necessarily have to be allied to you; the hit creature just needs to have something it perceives as an enemy within range.

For absolute clarity, you can ask yourself these questions, in order, to determine if you should add Sneak Attack damage to a creature you’re hitting with a weapon.

Are you attacking with a ranged weapon (shortbow, hand crossbow) or a melee weapon with the finesse weapon property (rapier, shortsword, dagger)? If not, don’t add sneak attack damage.
Have you dealt sneak attack damage this turn? If you have, don’t add sneak attack damage.
Did you make the attack roll with disadvantage? If you did, don’t add sneak attack damage.
Does the hit creature have a non-incapacitated enemy (such as one of your fellow party members or a third-party threat) within 5 feet of it? If so, add sneak attack damage.
Did you make the attack roll with advantage? If you did, add sneak attack damage.

Enabling and Empowering Sneak Attack

With these conditions established, you’re typically going to want allies to engage enemies you want to deal sneak attack damage to. This is by far the easiest way to ensure you’re getting those sweet bonus d6s to your damage.

Rogues don’t need that to occur, though, so long as you have a way to get advantage on your attack roll. This will pair well with Cunning Action and Steady Aim unlocked over the next two levels as they offer you ways to give yourself advantage on your own attack rolls, making you less reliant on allied positioning to function.

Another major consideration is in how often your Sneak Attack can be applied; once per turn means once on each creature’s turn, not just yours, and can be applied multiple times each round. With a reaction, this can be enabled twice per round. Attacks of opportunity are the most common way you can get this with no other aid, and encourages riskier melee builds over the safer ranged combat many rogues take.

If you’re partying with a Battle Master Fighter, they can get access to the Commander’s Strike maneuver, which can give you an attack outside your turn. Compulsion, a bard spell, and Voice of Authority, an Order Domain Cleric feature, both can perform similar roles as well, but they can be fairly niche to pick up on. I’d recommend talking with your bard, clerics, and fighters about this before subclass selection, as there aren’t many ways you’ll have on your own to empower this further.

Importantly, any character can make a weapon attack as a bonus action if they’ve taken the attack action that turn to attack with a one-handed light melee weapon in one hand and they’re wielding another light weapon in their off-hand. The second attack doesn’t add your Dexterity modifier to its damage, but still will help you deal Sneak Attack damage should you swing and miss with your first attack. This is why you’re likely going to want to have a pair of finesse, light weapons on you; having more opportunities to hit makes Sneak Attack more likely to occur on your turn. Improving this consistency is at the core of being a threatening rogue.

Expertise

What sets rogues up as one of the best skill-based users in the game is Expertise. Doubling your proficiency bonus for two skills of your choice you’re proficient with is incredible, and scales great. Every normal +1 bonus added to your proficiency as you level up adds two to the expertise skill, quickly turning your ability check modifiers to +10s and higher.

Stealth and Thieves Tool proficiency are common and excellent options for your expertise, but you don’t need to feel limited by these choices. Perception is easily the most used skill in the game. Expertise in Perception doubles up by applying to both your passive score and your modifier when making ability checks.

You’re also not limited to rogue skills; your background skills can get assigned your Expertise, making it possible for you to start with double proficiency in any skill you want. Want to be an expert zoologist? Animal Handling! How about a jealous magicless student? Arcana will deliver that feeling.

I’d highly encourage taking at least one commonly used skill (Perception or Stealth), and one other you feel bests fits your fantasy. If your aim is to play a classic thief, Stealth and Perception or Thieve’s Tools will deliver that fantasy for you.

Thieves’ Cant

Thieves’ Cant is more similar to a language than a feature; it's a mix of cultural understanding and coded words some worlds will lean into and make a major part of the story. Some tables will entirely ignore this feature, and honestly, that’s okay. It is a ribbon that opens up roleplay opportunities first and foremost. Most games aren’t going to make any use of this beyond its flavor. If you want it to be a more major part of your character, I’d talk to your DM about it ahead of time, as it’s a world-building element they have to consider when fleshing out the adventures and narrative.

2nd Level: Cunning Action

Cunning Action is the other major pre-subclass element rogues lean heavily on in combat. All three bonus actions are exceptional boons to any character that can take them, and will frequently give you a huge amount of options when combining them with other actions, even beyond just attack rolls.

Hiding

Hiding Rules. The Hide action specifically lets you make a Dexterity (Stealth) check in an attempt to hide following the rules for hiding to grant you the benefits of being an unseen attacker. The rules for hiding are long, and not particularly consistent table to table as at their core, the GM decides the circumstances appropriate for hiding.

I highly encourage you, the rogue, and your GM to review the Hiding, Unseen Attackers and Target, and Vision and Light rules when going into your first few session on a new rogue. Darkvision rules also can come into play here, and I’d recommend checking those out as well. Having a concrete idea of where and when you’ll be able to hide will have a massive impact on your character’s ability to navigate fights.

Some core considerations baked into the rules, though, include that you can’t hide from a creature that can see you clearly, and you give away your position if you make noise. Being Invisibile mitigates these restrictions.

Light levels in the environment also can contribute to your ability to hide; while not considered majorly at most tables, some will leverage dim light regularly. If you’re at one such table, the Skulker feat can enable you to hide in the dim light or other lightly obscured areas.

Typically, you’ll be able to consistently hide if you have multiple areas of full cover available to you in an environment. Being able to move from one to another and attack from different angles all will contribute to beating the enemies' contested Wisdom (Perception) checks and their passive perception scores.

Hiding Benefits. The main reason you’ll want to be spending a bonus action to hide in the first place is to become an unseen attacker. The rules specifically are “When a creature can’t see you, you have advantage on attack rolls against it. If you are hidden- both unseen and unheard- when you make an attack, you give away your location when the attack hits or misses.”

Advantage crucially gives you a way to enable your Sneak Attack on your own. Because re-hiding over and over doesn’t often result in being both unseen and unheard, it’ll often be restricted in fights to one or two times, but that’s often enough time for a melee ranged ally to engage your target, turning on your Sneak Attack without needing advantage.

Dashing

Cunning Action Dashing often will make you feel like the fasted member of the party at any given moment. Where Hiding is likely the most important on any given rogue for enabling their damage, Dashing is as useful for repositioning, getting to valuable locations, and escaping. Where Disengage and Hiding as a bonus action tend to only come up in initiative, Dashing comes into play both in and out as it functionally gives you a third dash each round when in a chase or determining how quickly you can cross a specific distance.

This is the option as a GM I tend to see most used round to round. Once their location is revealed from their initial attack, Dashing comes into play when the rogue needs to grab an important magical item or reach a downed ally with a healing potion.

Of all the options Rogues get, Cunning Action Dashing gives them the most opportunity to interact with combat on a supportive axis.

Disengaging

Bonus action Disengage is so nice to have. You can consistently break out of enemy threat ranges without spending actions, meaning you can back yourself up to safety while continuing to stick arrows or daggers into the threatening creature.

Because Sneak Attack wants you to be attacking enemies engaged with your allies, you’re often going to find this is an easy way to leverage melee ranged attacks while safely pulling yourself out of the fray. It keeps its focus on the barbarian while you shank it from the sides safely.

3rd Level: Roguish Archetype and Steady Aim

Rogue’s archetype is the most important choice you’ll have to make throughout your entire time playing the class. Each subclass offers its own means of interacting with the world, and will offer wildly varying results rogue to rogue.

Roguish Archetype

Rogue’s archetypes are pivotal in giving them utility beyond their core features. As their base class has no consumable resources, rogues that want big, splashy tools have to get them from one of these nine subclasses.

Arcane Trickster is the subclass I’d recommend most for an average rogue fan. It opens you up to a small pool of spells that work in tandem with your improved Mage Hand to do all the iconic sneak and stab things you’d want from a classic rogue. Bonus spells, even when they’re limited to 1st-4th level, give you ways to interface with the game you otherwise never could. Rogue’s stream of Ability Score Improvements past this point also makes maximizing your spell toolbelt and spell save DC easy peasy.
Assassin has a lot more infamy specifically because of how polarizing the Assassinate feature is. With setup, it can let you automatically crit and deal outrageous damage before a fight gets a chance to start. Paired with other features that improve radically when applied to a critical hit like Divine Smite and you’ve got a recipe to drop creatures from full to zero in the blink of an eye. Its core problem then tends to be functioning beyond situations where Assassinate is online, often leading to it feeling like a subclass that only contributes to a small percentage of your actual encounters.
Inquisitive rogues are odd ducks. Ear for Deciet makes them solid lie detectors (especially when compounded with Expertise), and Eye for Detail is fine in the first round or two of fights against sneaky enemies, but Insightful Fighting is such a non-feature it’s hard to consider this subclass. Rogue doesn’t get a lot else to empower them beyond this point outside of their subclass; Inquisitive doesn’t offer enough juice in the combat department, nor in the exploration tier of play for me to consider it compared to its competitors.
Mastermind kind of sets up your rogue as a support-damage dealer hybrid, with Master of Tactics giving you a bonus action Help with a 30 ft. range and Master of Intrigue providing a nifty mimicry feature for impersonation. It, too, suffers in the top-end department as its upper-tier features aren’t particularly compelling, but Master of Tactics gives advantage out every round for free, and that’s powerful enough to consider the option.
Phantom exists to fulfill our inner edge-lord fantasies, and I love it for that. Ghost Walk is the feature I definitely want most, and it arrivinging at level 13 is a huge bummer. I don’t love Whispers of the Dead, as the whole party normally will have access to whatever skills you’d need on a given adventuring day, but Wails from the Grave dishing out bonus scaling damage is perfectly reasonable. Tokens of the Departed is also a deeply rich fantasy fulfillment option; its not perfect, but I like Phantom a lot, and would recommend it to the rogue’s out there that want to be even more edgy.
Scout feels like it belongs in the Player’s Handbook; it is simple and solid. Skirmisher helps you play the melee rogue easier, with Survivalist giving you free expertise in both Nature and Surival. If you pick Scout, your core objective is likely about being fast and freely mobile, taking advantage regularly of your Cunning Action Dash paired with bonus speeds offered here. Its a little clunky that this doesn’t account for your expertise taken prior, so you have to know ahead of time to not take proficiency in either skill to get the most from this option. Its upper tier features aren’t amazing, but do lend to you feeling like an ambush leader meaningfully. One or two druid cantrips would have gone so far in making the option come together more, but where it stands now, it’ll give you tools to play a purely non-magical ranger-style rogue.
Soulknife gives rogues resources that it desperately wants. Psionic Power is fueled by psionic energy dice that recharge on a long rest. You can recharge a die once per short rest as well, and all of your abilities also get a free use per long rest, encouraging you to actually use all of the abilities offered. Psychic Blades is basically just a shortsword with a 60 ft. thrown range and an off-hand dagger. You get new abilities that spend the dice as you level, making it scale exceptionally well. If you want more to do with your rogue and more decisions to make fight to fight, Soulknife is a great choice.
Swashbuckler sells you on a fantasy of suave dueling but doesn’t really stick the landing when it all comes together. Fancy Footwork and Rakish Audacity want you to engage a single target but don’t really reward you for doing so. Sure, you now can engage a single lone target and get sneak attack damage on them, but tactically, you’re better off almost always bursting down single targets at a time as a group, which you can just as easily do with your base Sneak Attack feature. Swashbuckler compares poorly to Scout and similarly suffers from lackluster upper-tier abilities that you’ll infrequently find ways to use meaningfully.
Thief is iconic and tricky to play but can be deeply rewarding in the lower tiers. Fast Hands is the foundation of the option which eventually evolves into Use Magic Device, and will be what holds your build together for many levels. Acid, Holy Water, and Alchemist’s Fire are all going to be tools you’ll want to get the most out of Thief; it’s an option whose core features are hidden in the equipment section of the Player’s Handbook. Without a suite of items to throw out round after round, the option can feel pretty terrible, but with an assortment of bear traps and ball bearings, you can have a blast playing a Batman-style rogue with a billion tools for a variety of situations.

Steady Aim

Steady Aim is a functional improvement to Cunning Action that cleans up the class to work in a wider variety of environments more consistently. A bonus action for advantage on attack rolls without having to jump through the constant mess of hiding over and over again is a major upgrade at tables that don’t necessarily want to manage complex environments rich with cover and room for rogues to attack from a variety of spaces. It helps every rogue, regardless of how hiding and stealth rules are being run function. Even rogues dedicated to stabbing things with daggers should probably pick up a ranged option for their flexibility, and Steady Aim hammers that idea home.

Hopefully, Steady Aim is baked into rogue’s Sneak Attack in the next edition, or it receives some amendments to sure up some of the issues that pop up in a decent chunk of groups.

4th Level: Feat Considerations

Rogues have a somewhat complicated relationship with feats; they get a lot of them, but can’t use many of them as well as other martial characters. Sharpshooter, for example, wants you to make as many attacks as possible to get the most out of its +10 damage. On rogues, your making one shortbow shot a round that you really don’t want to miss, making it a fine option to improve your character, but not the backbreaking power-gamer feat it’ll be on rangers or fighters.

For this reason, I tend to encourage rogues to take a utility feat fairly early that offers some bonus spells or extra class utility, then look to max their Dexterity score as fast as possible after that.

Feats to Take

Fey Touched, Shadow Touched, Ritual Caster, and Magic Initiate all are excellent feats for empowering your magical capabilities. Rogues are fundamentally infiltrators and sneaky damage dealers; all of these options offer you tools to engage your non-combat missions in powerful new ways you can take advantage of more so than most other characters. An invisible rogue with expertise in Stealth is going to be nearly impossible to track. Familiars from Find Familiar can give you sight and sound when you’re laying in wait for the right opportunity to strike, and double up as exceptional espionage and infiltration tools in their own right. For the same reasons I recommend Arcane Trickster so highly, all of these feats will be major boons to just about every rogue character sheet.
Crossbow Expert is the biggest combat boon rogues can typically take, getting a bonus action ranged attack that can scale with Sharpshooter down the road. Having a weapon attack compete with your bonus action is a bit rough with how many options rogues get from their core Cunning Action and Steady Aim to their subclass options like Mastermind’s Master of Tactics. Still, two attacks a turn is a lot, especially in the early tiers, and opening up your damage to be diversified over your Sneak Attack multiple hits with high Dex modifiers can be a way to deal substantially more damage round to round.
Sharpshooter on rogues with Crossbow Expert feels excellent, as two attacks a turn with a potential of +20 damage and Sneak Attack is yucky good. +10 is still fine and has massive potential to hit hard early, but it won’t scale on rogue the same way it does on the other martial characters, making it substantially worse. Still, if you’ve got a +5 Dex already and want to hit harder, Sharpshooter certainly will help you do that.
Slasher and Piercer both can work with some common rogue weapons (shortswords/shortbows respectively), and come with a +1 Dexterity by default. If you’ve got an odd Dexterity score, these will typically be better than a normal Ability Score improvement.
Poisoner is a cute option to empower a rogue that may lack other means of empowering their attacks. 2d8 potential bonus damage and the poison condition on archetypes like Scout or Phantom can be a meaningful improvement you’re happy to play with. In most other classes I tend to recommend steering away from Poisoner, as they have spells and other resources to readily empower their damage. Most roguish archetypes don’t get these, and thus can fall back on Poisoner to give them a bit more juice.

Feats to Avoid (Most of the Time)

Alert is something you take on exactly Assassin or Scout rogues with the expressed goal of always getting your 1st round features. If you aren’t in either of those subclasses, you’re often going to want to act after your allies, as then Sneak Attack is set up easier for you.
Skulker is a table-dependent feat that needs low-light Hiding opportunities to be worth using. If you aren’t regularly making Wisdom (Perception) checks at disadvantage from dim light, you probably aren’t going to make much use of Skulker and will be better off with most other feat options mentioned above. Some tables can make use of this, but with the game changing to showcase big set-piece encounters over dungeon-crawling monster menagerie type games, Skulker is getting less and less room to shine.

5th Level: Uncanny Dodge and Sneak Attack Scaling

Rogues get shafted at 5th level. Fighters, rangers, barbarians, monks, and paladins all get Extra Attack, doubling their typical action efficiency in combat and empowering any weapon attack based feats they already have. Druids, clerics, wizards, sorcerers, warlocks, and wizards all get 3rd level spells which reshape what kinds of encounters can challenge players while unlocking new out of combat tools that challenge the laws of physics.

Uncanny Dodge is what rogues get instead of any of these core scaling options: a defensive reaction to halve an attack's incoming damage. Sure, its nice to have, but it doesn’t come anywhere close to competing with all of the juice every other character gets here.

That’s where their Sneak Attack Scaling comes in. Every other level, you get a bonus Sneak Attack damage die. Going from 2d6-3d6 damage isn’t all that exciting, but getting a bonus d6 at 7, 9, 11, 13, 15, and 17 steadily improves your damage as the game progresses. Most other classes out scale this with more attacks or spells that deal substantially more damage than their lower-level options. Still, it is entirely reasonable to have an attack get moderately better every other level, as it’s the core of your character’s combat.

6th Level and Beyond

Most of your remaining features are defensive boons (Evasion/Slippery Mind/Elusive), skill improvements (Reliable Talent), or Ability Score Improvements/Feats.

Evasion

There isn’t anything too complex about Evasion; it's a great defensive feature that helps you shrug off big damage effects consistently at 7th level. A great feature to have on most any rogue, but especially those looking to play back to back with a melee ranged fighter or paladin.

Reliable Talent

What defines rogues the most as “experts” is Expertise, but Reliable Talent at 11th level is a close second. With this ability you just stop failing the majority of skill checks you can make. Paired with expertise, you’re looking at minimum results of 16 with no other ability score modifier considerations. Stack on top of this your numerous Ability Score Improvements and you're left with a character who succeeds at basically any relevant skill check they’re proficient with.

Blindsense

Blindsense is a sensory effect that comes way too late in the class to feel impactful. Druids have had access to a blindsight since they unlocked Wildshape at 2nd level, and numerous classes have access to spells that provide various vision types. Even fighters and rangers can take the Blind Fighting fighting style to get a feature akin to this 14th level ability.

Slippery Mind

Proficiency in Wisdom saving throws is excellent. I don’t want it as a feature, though. I want cool new toys to play with. This is a major passive boon that should come with at least something new to do at 15th level.

Elusive

18th level offers Elusive, making you incapable of being attacked with advantage, which is technically fine. Does it come close to competing with the likes of Wish and True Polymorph? No! Not even remotely close!

Stroke of Luck

Where Elusive is not even remotely comparable to other top tier features, Stroke of Luck absolutely does. Being able to guarantee a hit when you need it or turn any failed ability check to a 20 is genuinely powerful. Once per short or long rest does tend to be a bit too infrequent, as again, 9th level spells are once per long rest and can deal 40d6 damage to three massive areas, but Stroke of Luck can guarantee a hit when you need it most, and that’s the closest rogue gets to these kinds of powerhouse features outside their subclasses.

Building a Rogue

Rogues are probably the most streamlined characters to build, as they want to do one thing each round: Sneak Attack. That single feature shapes what weapons you use, what your Ability Score distribution probably is, and how you approach every fight.

Beyond enabling Sneak Attack, rogues are all about their utility out of combat. Without feats and multiclassing, their pigeon-holed into being skill monkeys that rely on huge numbers to impact gameplay. Magic enhances their character sheets massively, as pairing daring and challenging skill checks with powerful enhancement magic that gets them exactly where they want to be with a suite of tools for engaging the world beyond the norm sets rogues up for out of combat excellence.

The Sneak Attack Core

When you’re building a rogue, you’re basically going to always want a shortbow or pair of hand-crossbows and a pair of shortswords with some daggers. Every rogue will be able to use all of these tools with just a high Dexterity modifier, and enable your thrown/melee attacks alongside great ranged options to attack from a distance, all of which can enable Sneak Attack. A rapier can be a small damage dice improvement if you want to forgo an off-hand attack option, but for the most part on every non-Soulknife rogue, these weapons are going to be what you’re working with for the majority of the game.

You can have a preference for melee or ranged combat with the predominant force compelling melee ranged combat being an opportunity for attacks of opportunity and the bonus action off-hand attack. Ranged gameplay is way more flexible and far safer.

Crossbow Expert + Sharpshooter

With Crossbow Expert, you make up for the lacking off-hand attack to make your Sneak Attack happen in more of your turns. Stacking Sharpshooter on top of that will give you a massive damage bump, with the potential of 2d6+30+Sneak Attack damage each round. This particular build won’t scale as well on rogue as it will on the extra attack classes but is still one of the most powerful directions to go with on a 20-level rogue.

Unfortunately, this is kind of as good as rogue gets on its own. If you want to empower your rogue beyond your scaling Sneak Attack dice, you’ll have to dip around in other classes to fulfill that need, or build towards specific spells obtained within feats like Invisibility or Find Familiar.

How to Multiclass Rogue

Rogue is juiced in its first three levels; Sneak Attack, Expertise, Cunning Action, and their subclass all offer a huge swath of power for just three levels. After that, it’s basically all down-hill when it comes to new offensive options or ways to engage the world in unique ways outside the subclasses. This heavily encourages multiclassing, and my god does it pair beautifully with rogue.

Martial Multiclass Options

Assassinate is a wacky feature that breaks the game in half when abused to its fullest. Critically hitting any surprised creature doubles your dealt Sneak Attack damage, sure, but why critically hit with just one or two attacks when five levels in paladin, ranger, or fighter open you up to critically hitting with four or more attacks at once? Add in paladin’s Divine Smite with all the spell slots you’ve got and you can obliterate an encounter with a massive explosion of damage before it starts.

Outside Assassinate, fighters offer you martial weapon proficiency (crucially including heavy crossbows for a d10 dice upgrade) and a Fighting Style (typically Two-Weapon Fighting or Archery). A 2nd level in fighter provides you with Action Surge, which pairs splendidly with Cunning Action to give you opportunities to Dash ludicrous distances or take complex turns involving attacking three different creatures from various positions all at once. One more level opens up a subclass opportunity, namely Battle Master, which plays beautifully with the scoundrel rogue fantasy of throwing sand in their eyes or hitting them in the groin to drop them prone. If you want to stick with a non-magical character, fighters are a great direction to go.

Rangers similarly offer you relevant fighting styles and weapon proficiencies but also give you access to Favored Foe, Deft Explorer (Canny), and 1st level spells for just a two-level dip. A 3rd level can give you a ranger subclass, many of which include useful pets or subclasses like Gloom Stalker to hit home the master of shadows fantasy you might be looking for. Hunter's Mark can help you feel like your Sneak Attack damage is still scaling up while also getting all the bonus goodies that come with a few ranger levels.

Spellcasting Options

Warlocks are another option that lends itself well to multiclassing. The first three levels in warlock are loaded with power; just one level gives you a spell slot, subclass, and cantrips, with two offering another spell slot and Eldritch Invocations, and a third offering you 2nd level slot upgrades and a Pact Boon. Hexblades obviously pair well with rogues in the stabbing department; Archfey is also a great route to consider, as their spell selections are tooled for high mobility and deception, both things rogues adore.

Any of the other full-caster options tend to offer a ton of juice to rogue as well. Anything that adds damage on hit for a 1st level slot can keep you feeling like your damage is going up while simultaneously opening up free cantrips and other class resources. It makes dipping two to three levels in other classes feeling like it costs close to nothing.

Druid is a personal favorite of mine, as Wild Shape is an incredibly fun feature to pair with a stealth based rogue sneaking around, and their spell list includes high utility spells like Entangle and Fog Cloud rogue’s can make great use of. Stack on top of that Summon Beast or Moonbeam damage each round and you’re set up to consistently hit like a bus while thriving surrounded by useful magic for gumming up enemies movement and impairing their vision.

Munchkin Nonsense (AKA: Assassinate Was a Mistake)

The most abusable feature in rogue, by a lot, is Assassinate. Assassinate gives you a way to guarantee crits.

Rules Around Surprise

To understand the raw potential of Assassinate, its first crucial to understand how surprise works. The rules are simple and are used when rolling initiative to determine who is surprised. From the OGL:

“The GM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the GM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.”

Being surprised is similarly simple: “If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a reaction until that turn ends.”

This functionally acts as a condition; a creature is surprised for the entire round, regardless of what happens to it. No matter how many times you hit it, it remains surprised, which is important, as Assassinate makes every attack you hit with a critical strike against surprised creatures. You can sink as many hits as you have into a single surprised creature for LUDICROUS damage, all thanks to Assassinate!

Notably, surprise uses different rules from Hiding. Just because a creature is surprised doesn’t mean you have advantage on attacks made against them; that normally coincides with attacking from an unseen place, which results in the first attack being made with advantage and subsequent attacks being made without advantage (unless something else is granting you advantage).

What All Stacks with Assassinate?

To munchkin Assassinate to its fullest, you’re going to want two things: extra attacks, and features that empower a weapon’s damage. The critical hit rules state “Roll all of the attack’s damage dice twice and add them together”, which means if you can improve the attack’s damage dice, it’ll double.

Sneak Attack states “you can deal an extra 1d6 damage to one creature you hit with an attack”, which has been confirmed to say the weapon is dealing the bonus d6 damage. The important words there are “you hit with an attack”, as they are somewhat shared with the Divine Smite feature’s wording “in addition to the weapon’s damage”. Divine Favor says it most cleanly: “Your weapon attacks deal an extra 1d4 radiant damage on hit”. Hunter’s Mark and Hex are both spells that add a d6 damage on hit, which means they can critically hit. Gloom Stalker’s Dread Ambusher feature deals a bonus d8 damage on the second free attack they get, and yup, that damage can crit as well!

Big Damage Options for Assassinate

What gates the potential for Assassinate is straightforward. Every character gets a set amount or resources to use on their turn, and a set amount they can have prepared ahead of time. Characters have an action, bonus action, reaction, and move on their turn, with a one spell they can concentrate on. To do as much as possible on our own, with no outside help from other party members, we’re going to need to juice as many of these options as possible while adding on extra free resources from classes outside rogue.

For our race, we have to go with Half-Orc, as Savage Attacks adds a bonus weapon die on each of our critical hits.

Sneak Attack only applies once per turn; this majorly gates how much potential damage it can do, so we’re not going to stick around past 3rd level in rogue, as we can get a lot more damage out of other options.

An easy place to start is paladin; Divine Smite damage critically hits, and has a base damage equal to 1d8 + an expanded spell level. It's also important to note that there isn’t a cap on the number of times we can smite per turn, just a limitation of one per hit. This means as long as we can keep making attacks and have enough slots to fuel it, we can divine smite on each attack made. With 5 levels in paladin, then, we’ve got access to six slots that can critically hit and the Extra Attack feature for two attacks in our first round of combat against a bunch of surprised enemies.

Next on the agenda is to get more attacks, as two is far too few. Bonus action attack options are a dime a dozen and can be made with an off-hand attack at no extra class cost, making it easy to default to a pair of shortswords. Gloom Stalker Ranger’s Dread Ambusher feature gives us a fourth free attack as well as some extra spell slots to play with for only three levels.

Ranger’s Hunter subclass comes with Hunter’s Prey, which offers Horde Breaker for an additional free attack against a different creature, and eventually Whirlwind Attack at 11th level that can give you a number of attacks equal to the number of creatures you can get within 5 feet of you for a MASSIVE nova of up to eight attacks at once, which is a spicy direction to consider, but not all that consistent. For this example, we’ll stick with Gloom Stalker for single-target consistency.

Fighter is the next class we’re visiting for their Action Surge feature; with just two levels into fighter, we can now make three extra attacks: two from the additional Attack action, and one from Dread Ambusher giving us a free extra attack anytime we take the attack action. With a 3rd level, we can pick up Battle Master Fighter for four maneuver dice, and a 5th maneuver die from the fighting style for five of our attacks.

At this point, we’re 14 levels in, and are making seven attacks with our action, extra action, and bonus action. We can get an eighth attack through the Haste spell, which could ask us to invest five levels into a full-caster. Alternatively, we can be the Oath of Vengeance paladin subclass and instead need to spend just four more levels in Paladin to get access to it from our Oath of Vengeance bonus spells. 11th level Paladin gives us Improved Divine Smite, which deals a bonus d8 radiant damage to each one of our attacks, meaning we’re definitely committing to our final levels in paladin.

Quick note: Dread Ambusher, unfortunately, doesn’t also work with Haste, as Haste’s limitation supersedes Dread Ambusher’s additional attack opportunity.

We’ve got two Ability Score Improvements to play with this build from our 11 levels in paladin. With a Dexterity of 17 (as high as we can get with Tasha’s Ability Score Assignment variant and a 27 point buy), we can one of these to get our Dexterity score to 19, and improve it to 20 with a feat that bumps up our Dexterity score by 1 for +5 to all of the hit and damage of these attacks. Piercer deals a bonus die of damage when we critically hit with a piercing weapon (like our shortswords), and also gives us a bonus +1 Dexterity. Gross!

Critically, our 3 levels in ranger paired with our 12 in paladin give us two fourth level spell slots, three 3rd level, and three 2nd level to maximize our spell slot usage for our single explosion of damage.

Math Time

This build is a 20th level Half-Orc; three levels in Assassin rogue, three in Gloom Stalker ranger, three in Battle Master Fighter, and 11 in Oath of Vengeance Paladin. Our three fighting styles are Two-Weapon Fighting, Superior Technique, and Dueling.

We start it off by casting Haste while hidden and wielding a lone shortsword. Then, we initiate a fight. So long as we have get the drop on enemies and at least one is surprised, we do the following:

Take the Attack Action with shortsword in one hand for three attacks, using one 4th level slot and two 3rd level slots with Divine Smites and our Battle Master Maneuver dice

First hit with advantage uses Trip Attack to attempt to knock target prone
If the target passes, subsequent maneuvers attempt to trip until prone
Once prone, you can use any maneuvers that add d8 to damage on hit

Make the Haste extra attack with a 3rd level slot Divine Smite with one maneuver
Draw our second shortsword as part of our next attack action (taken using Extra Attack) for three additional attacks using three 2nd level spell slots with Divine Smite and our remaining little superiority die
Bonus action off-hand attack for two-weapon fighting with a 1st level Divine Smite

We sequence it this way to add dueling to four of our attacks, but we have to drop dueling for an extra bonus action attack to qualify for two-weapon fighting.

Damage by Source

Shortsword: 16d6

Piercer: 8d6

Savage Attacker: 8d6

Divine Smites:10d8+8d8+8d8+8d8+6d8+6d8+6d8+4d8

Sneak Attack: 6d6

Improved Divine Smite: 16d8

Battle Master Maneuvers: 8d8+2d6

Dread Ambusher: 4d8

Dueling: +8

Dexterity: +40

Damage by Attack:

1: 2d6+1d6+1d6+2d8+2d8+10d8+6d6+2+5

2: 2d6+1d6+1d6+2d8+2d8+8d8+2+5

3 (Dread Ambusher 1): 2d6+1d6+1d6+2d8+2d8+2d8+8d8+2+5

4 (Haste): 2d6+1d6+1d6+2d8+2d8+8d8+2+5

5 (Action Surge Attack Action): 2d6+1d6+1d6+2d8+2d6+6d8+5

6: 2d6+1d6+1d6+2d8+6d8+5

7 (Dread Ambusher 2): 2d6+1d6+1d6+2d8+2d8+6d8+5

8 (Off-Hand bonus action): 2d6+1d6+1d6+2d8+4d8+5

Total: 84d8+40d6+48

Or roughly 566 average damage.

This is by no means the most possible damage you can deal with Assassinate; it just happens to be the quickest and dirtiest I could think of. You can probably do more damage with a Greatsword (adding an additional 16d6 damage if you can get the bonus action attack from something else), plus it can use Great Weapon Fighting fighting style to reroll 1s and 2s to reduce minimum rolls, of which there will be many!

Fun munchkin stuff to be had with Assassinate; you’re left entirely void of resources after you nova, but when you nova for more damage than Tiamat has hit points, you can’t be that upset with the cost.

Despite Their Flaws, I Adore Rogues

Outside of the munchkin nonsense, rogue isn’t a particularly powerful class when stacked up against full-casters or extra attackers. Still, the scaling damage is enough alongside Cunning Action with subclass like Arcane Trickster and Soulknife able to do a lot of heavy lifting outside of combat with exploration and social interaction. I’d highly recommend multiclassing with it, as that’ll open up worlds of magical opportunities alongside martial combat prowess, but if you want to stick it out for all 20 levels, rogue can still satisfy at most tables.

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Rogue 5e