D&D 5e: Assassin Rogue Guide

D&D 5e: Assassin Rogue Guide

Role in the Party

Rogues might be sneaky thieves, dashing musketeers, or courtly provocateurs. But it’s the tales of the Assassin that hold the most dread. 

Every tavern has stories of black-clad butchers dropping from rooftops, a poisoned blade delivered from within a crowd, or a high-profile noble who was discovered dead inside a still-locked room. Near indistinguishable from other Rogues, the Assassin likes to take its time, slowly stalking prey like a spider, only striking in a burst of speed and ferocity when its prey is tight within its web with no chance to escape. 

As comfortable stalking the edges of the battlefield as they are holding court with kings, this guide details the abilities of the Assassin subclass, effective ways to build one, as well as skills, multiclass options, and other things any player of the class might need to know.  





The Assassin Rogue subclass is found in the Player’s Handbook. Click here to pick up your own copy of the Player’s Handbook!

Assassin Features

Bonus Proficiencies: When the Rogue takes this subclass, they gain proficiency in the Poisoner’s Kit and Disguise Kit. Two free proficiencies are nice, and the Rogue can gain some use from these, especially when combined with its later abilities. 

Assassinate: The key ability of the Assassin. In the first round of combat, the character gains Advantage against any creature that hasn’t had a turn yet. This is simple but effective, and all but guarantees a landed sneak attack if the Rogue gets a decent Initiative roll. 

Most Rogues are going to have high DEX, but to maximize this ability the Assassin should look for other ways to boost their Initiative. The Alert feat is a good start, but there are several other class abilities and spells that can also do the job. Get these if possible, as not going first massively hampers what this subclass needs to do. 

The second part of the ability guarantees a critical hit if the Assassin attacks someone who is surprised. 

This is far harder to achieve. Surprise is heavily determined by GM fiat, and requires that the entire party be stealthy because, in order to even qualify for surprise, a creature has to not notice any threats

Realistically, this means that unless the Assassin is operating solo, which is both anti-party and incredibly risky, having just one character tromping around in heavy armor makes surprising enemies almost impossible, at least in the lower levels where there are fewer ways around it. 

Still, if the party has time to set up an ambush, or during a social situation the Assassin shanks someone with a hidden blade out of nowhere, the guaranteed crit is an absolute pile of damage that’s likely to almost or outright kill any appropriately scaled enemy in one attack. 

Infiltration Expertise: From 9th level, the Assassin can create the necessary documents and details for a convincing false identity. 

This takes 7 days and 25gp but creates an identity that’s secure enough that, unless a creature has an actual reason to doubt it, passes without questions or needing to roll. 

This is a wholly out-of-combat ability, and it’s unfortunately surprisingly niched. In the campaigns where the party has 7 days, the inclination and the need to create an ironclad secret identity are unlikely. Still, the lack of counters to this is nice, and rolling into town with a brand new and ridiculous backstory makes for some great RP moments. 

Imposter: From 13th level, the Assassin can learn to mimic the mannerisms of other creatures. This takes three hours of observation and lets the character impersonate the chosen target. From that point, the Assassin can pass as that person without issues, and any Deception checks necessary are made with Advantage. 

This is awful. The Actor feat can do basically all of this, from level 1, with 1 minute of casual observation instead of 3 hours. For an ability gained at this level, it’s drastically underpowered. 

Death Strike: From level 17, if the Assassin attacks a creature that’s surprised, it has to pass a CON save (8 + DEX + Proficiency bonus) or take double damage from that attack. 

To reiterate, the attack from surprise will also be an automatic critical hit, from the Assassinate level 3 ability. So the total damage is double the result on 20d6. That’s an average of 140 damage, or more than half the HP of an Adult Red Dragon, an equivalent CR17 monster. 

We’ve already discussed the issues with surprise under the Assassinate ability. But at this level, and with this much damage on offer, it’s probably worth trying to find situations where the Assassin can do their thing because a single Death Strike can change the entire flow of an encounter on a single dice roll. 


The Assassin is built around one thing. Picking a single target and murdering them until they’re dead. It’s also very very good at this, pouring on the damage turn after turn. Built right, it’s common for the Assassin to cause a key enemy to start an encounter nearly dead, especially typically squishy targets like mages. 

The base kit of the Rogue helps with this goal, giving the Assassin the tools it needs to perform quick kills and keep itself safe in the process. Weapon proficiencies offer everything the class needs, Cunning Action gives mobility and stealth, and Uncanny Dodge makes for a surprisingly effective defensive layer against big single attacks. 

Outside of combat, the Rogue is one of the most varied and useful classes in the entire game. No other class comes close in skill uses, except possibly the Bard, and even then the Assassin packs in a plethora of Tool proficiencies (at least 3) that the Bard simply can’t match. 

A Rogue can be built to fill any niche in the party’s skill profile. It comfortably fulfills the role of face, is the quintessential sneaky scout, and can quite easily shift into lore-monkey, with multiple knowledge skills at its fingertips. 

One often overlooked strength of the Rogue class is its ability to stack Sneak Attacks. The Sneak Attack ability can be used once per turn, not once per round. Certain feats and class abilities (Sentinel feat, Order Cleric’s Voice of Authority, and Battle Master Fighter’s Commander’s Strike, for example) can allow a character to take an out of sequence attack. So if you’re building a party together, it’s worth floating the idea of these abilities if players are taking any classes that offer one. 

On a subclass that’s as dependent on, and whose combat power mostly lies in, their Sneak Attacks, doubling the number of attacks made can double or triple the first round DPS of the character, and can almost ensure that one enemy is made decisively dead before they ever get to act. 


The first big weakness of the Assassin class is how linear it is. In combat, it’s going to try and find a way to Sneak Attack. And then, once it’s done that, it’s going to Sneak Attack. From there, it probably wants to Sneak Attack. Repeat until anything hostile stops moving. 

This limits the class’s combat utility and can get slightly dull for the player piloting it. Other subclasses try and fix this with spells, or a bonus action help, or turning the Rogue into a solo duelist. But the Assassin, strong though the ability is, just does the same thing, turn after turn. 

The subclass also doesn’t offer anything that affects combat outside of the first round. Once the first round has passed, or worse, if the Assassin flubs their initiative roll, the character is simply just another Rogue, with no way of triggering their sole combat boost. 

There’s also nothing here to fix how squishy the class can feel. Cunning Action and Uncanny Dodge help, but if an enemy genuinely wants you dead, a d8 hit dice and light armor proficiency don’t go far. An Assassin venturing into melee would do well to pick up some other form of defense. 

Finally, despite having tons of skills and tools, the Assassin is purely mundane. Flashy as it is to land a critical strike and roll the entire dice box onto the table for damage, many of the class’s later abilities that are based around sneaking and infiltration could have been handled by a spellcaster, and normally don’t even require particularly high-level spells to mimic. 

That means the Assassin can sometimes feel overshadowed in its out-of-combat role, and it can take a little work to get the later abilities of the subclass to feel relevant. That’s unfortunate for a character that’s flavored as somewhere between Assassin’s Creed, and Batman. 

Best Race Options

A quick addendum on races: The Assassin, more than any Rogue, wants to be sneaking around and getting the jump on enemies. Darkvision is almost essential for effective stealth in a lot of environments, so look for Races that come with Darkvision built into their ability list. 

Owlin: Stealth proficiency, Darkvision, and a language, as well as a permanent flight feature that’s only limited by having to wear light armor? This is as close to perfect a race possible for the Assassin. 

Bugbear: The stats aren’t amazing, so talk to your GM about customized origins. But Stealth proficiency, Darkvision, a 5ft increase to melee attack range and bonus damage in the first round of combat make for a hilariously effective close range Assassin. 

Tabaxi: Perfect stats, two amazing skills, Darkvision, a climb speed, and the ability, essentially once per encounter, to double your speed for free. On a class that can Dash or Disengage as a bonus action, that means you’re always where you need to be.  

Choosing the Right Skills

Unlike most other classes, the Rogue has very few limits when it comes to skills in character creation. At least 6 skill slots from class and background, proficiency in Thieves Tools, and built-in Expertise right from level 1 means that the Rogue is the undisputed master of skill checks. 

For the Assassin, Perception and Stealth are near-essential, and might just be both of its Expertise choices as well. The ability to see enemies coming, then hide from them in ambush, is almost the entire subclass. 

From here, the Assassin can take whatever is necessary, or simply whatever seems fun. Social skills like Deception and Persuasion are incredibly useful both for what this character probably wants to do, and if the party doesn’t have another Face. 

Alternatively, Survival and Athletics push the build towards more of a Hunter, roaming the wilds or perched in treetops, waiting for their mark. 

Finally, knowledge skills and Tools are always handy, and an Assassin who picks up some of these might also use them to flesh out the background of false identities created through their Infiltration Expertise ability.  

Fitting Feats

Alert: The Assassin needs to go first for all of its abilities to activate in combat. A +5 to the roll is a significant boost to the chances of getting the drop on the enemy. Prevention of surprise also means if the GM tries to pull the same tricks on you, they automatically fail, which is nice. 

Skulker: This feat brings a whole bunch of benefits to sneaking around, all of which meshes perfectly with the Assassin class. 

The ability to hide when lightly obscured works perfectly with Cunning Action. Dim light becomes less of an issue. But most importantly, the Rogue can make ranged attacks from hidden, fail to hit, and stay hidden without having to make any sort of check. Did you miss? Who cares! Keep sniping until you hit something. 

Shadow Touched: The ability to cast Invisibility once per day is almost guaranteed surprise on a lot of enemies, which normally results in one of them ending up dead. The other spell option might be Cause Fear or Silent Image, both of which are handy to have.   

Optimal Backgrounds

Guild Artisan: Two decent skills, an Artisan’s Toolkit, and a language is a decent variety of skills to add to the Assassin chassis. 

Charlatan: Twin social skills and two of the essential Roguish Toolkits. One is also granted by the subclass at level 3, so you can pick any Tool of your choice to build out the character. 

Courtier: Two social skills and two languages help the character blend in, with an easy background masquerading as a highborn killer. 

Multiclassing Options

Gloomstalker Ranger: If any subclass is built to multiclass with the Assassin, it’s the Gloom Stalker. The subclass delivers an absolute pile of first round benefits, as well as one of the most powerful stealth abilities in the entire game, all at level 3. 

During the first round, the character gains a 10ft boost to their movement speed, a small bonus to damage on an attack, and the ability to attack an extra time, all for free. The Gloom Stalker also lets the character add their WIS modifier to their Initiative, helping to ensure it gets that first turn. 

On top of this, the build gains Darkvision, or a range increase if it already has it, and ignores enemy Darkvision. For a character that probably has Expertise in stealth, the ability to flatly ignore one of the fundamental ways enemies might notice you are just incredible. 

A 3 level dip is enough for this multiclass to function, but it could also happily take 5 levels or more of Ranger for Extra Attack, the Pass Without Trace spell that gives +10 to Stealth, and other benefits. 

Armorer Artificer: The Artificer is a class that has an absolute ton of utility, including making its own magic items, and a great spell list with a lot of powerful low level options, including the Booming Blade cantrip for stronger Sneak Attacks. 

But we’re taking this dip to turn our Assassin into a walking tank. Proficiency in all armors, backed up with ignoring STR requirements, lets the Rogue wear full plate and shield without issue if they decide to. 

And choosing the Infiltrator armor model increases the Rogue’s move speed, lets them ignore Disadv on stealth if the armor would inflict it, and builds in a permanent lightning blaster that can be used to sneak attack at range, in a hard to resist elemental damage type.  

Hexblade Warlock: The Hexblade works great alongside any Rogue, but particularly benefits the Assassin. One level lets the Warlock use their CHA for attack and damage rolls on a weapon of their choice, plus a bonus action curse, some heavier armor, a spell slot, and the best cantrip in the game. That’s easily enough to justify the dip.  

Two levels offer Invocations. Mask of Many Faces lets the character cast Disguise Self on themselves without limit, which works perfectly with the later infiltration abilities of the class. 

At third level, Blade Pact gives the Assassin a magical weapon that can be shunted into extradimensional space, so they can always sneak their armaments into any situation. Improved Pact Weapon also allows it to take the form of a bow or crossbow, in case the character is focusing on ranged attacks. 

Would I recommend playing an Assassin Rogue?

The Assassin is the simplest Rogue subclass, at least mechanically. It wants to find a way to land it’s hard-hitting first round sneak attack, then keep doing that every turn until all its enemies are dead. 

Out of combat, it’s likely to act as the party Face, handling a lot of the social load, and perhaps using its imitation skills to get close to someone the party needs to meet (or kill.) 

Newer classes might indeed have more to offer, with padded out subclass lists and more flexible abilities, but the Assassin still has a place. What it does is relatively straightforward, but as this guide has shown, the Assassin is also a fantastic starting point for a lot of strong multiclass builds that can help fix that.

Plus, those times where you land that critical smite, roll high, and one-shot a major enemy will never not feel amazing.  


Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *