Assassin 5e

Grand Master Assassin

5e SRD >Gamemastering >Monsters & Foes >NPCs >

Medium humanoid (any race), any alignment

Armor Class 17 (studded leather)
Hit Points 104 (16d8 + 32)
Speed 35 ft.

13 (+1)20 (+5)15 (+2)15 (+2)16 (+3)16 (+3)

Saving ThrowsDexterity +9, Intelligence +6, Wisdom +7
SkillsAthletics +5, Acrobatics +10, Deception +7, Insight +7, Investigation +6, Perception +11, Sleight of Hand +9, Stealth +13
Sensesblindsight 10 ft., passive Perception 21
Languages Thieves’ Cant plus any three languages
Challenge 14 (11,500 XP)

  • Assassinate. During its first turn, the grand master assassin has advantage on attack rolls against any creature that hasn’t yet acted in the combat. Any hit the grand master assassin scores against a surprised creature counts as a critical hit.
  • Cunning Action. On each of its turns, the grand master assassin can use a bonus action to take the Dash, Disengage, or Hide action.
  • Evasion. If the grand master assassin is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, the grand master assassin instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.
  • Practiced Impersonator. The grand master assassin has advantage on any Intelligence ability check to disguise themselves.
  • Sneak Attack (1/turn). Once per turn, the grand master assassin deals an extra 31 (9d6) damage when it hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the grand master assassin that isn’t incapacitated and the grand master assassin doesn’t have disadvantage on the attack roll.
  • Multiattack. The grand master assassin makes two Rapier attacks or two Dagger attacks.
  • Dagger. Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4 + 5) piercing damage.
  • Shortsword. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 5) piercing damage.
  • Light Crossbow. Ranged Weapon Attack: +9 to hit, range 80/320 ft., one target. Hit: 9 (1d8 + 5) piercing damage.

The grand master assassin can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. The grand master assassin regains spent legendary actions at the start of its turn.

  • Grasp the Advantage. The grand master assassin makes one rapier or dagger attack on a creature within range that has made an attack this round.
  • Poison Weapon (costs 2 actions). The next melee or ranged weapon attack the grand master assassin makes is poisoned, and the target that takes damage from it must make a DC 15 Constitution saving throw. On a failed saving throw, the target takes 24 (7d6) poison damage, or half as much damage on a successful saving throw.

Section 15: Copyright Notice

City of Brass ©2018 Frog God Games; Authors: Casey Christofferson and Scott Greene


Featured art by 000fesbra000. Creative Commons License.
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The Assassin is a Rogue subclass I want to love, but it has severe flaws. Surprising enemies can be difficult for players to achieve, and that goes double for new players. I don’t know a player who doesn’t love to get critical hits, so the Assassin should be one of the most fun roles in the game. I have reworked this Roguish Tradition to better function as an executioner who uses steel, poison, and infiltration to snuff out a target and live to collect the bounty.

I offer a quick explanation for my text formatting so you can quickly discern between my homebrew suggestions, what already existed for the subclass, and my commentary. Italicized text indicates my homebrew alterations to Assassin Rogue features. The entire description of each feature is bolded, and my commentary is found below each feature in normal text.

Level 3 – Tricks of the Trade [Reworked/Renamed]

At the 3rd level, gain proficiency with disguise kits, poisoner’s kits. Your proficiency with poisoner’s kits can apply to Intelligence (Nature) checks and Charisma (Persuasion) checks to obtain or harvest poisons.

Your resourceful efficiency allows you to craft disguises and poisons at half the cost and time required. You have resistance to poison damage due to your time spent building up your tolerance.You may also apply poison to a weapon or ammunition as a bonus action instead of an action.

Studying behavior has given you a cerebral ability to influence others. You may use your Intelligence modifier instead of your Charisma modifier when you resolve a Charisma-based skill check.

Firstly, I changed the name of this feature because “Bonus Proficiencies” was boring and unreflective of my version. Assassins rely heavily on rolling well for Initiative. You can’t surprise a creature that outranks you in the Initiative Order because they cease to be surprised after they effectively lose their first turn in combat. It is unpleasant to invest time approaching a target to find that the target rolled exceptionally well on Initiative, taking its turn first and negating the Assassinate feature. For this reason, I allow the Assassin to add its proficiency bonus to Initiative rolls.

It was recently pointed out to me in a YouTube comment by Joel D that poisons are normally obtained through purchase or harvest, though it’s offset by Xanathar’s rule about giving bonuses when proficient in both tools and accompanying skills. I updated Tricks of the Trade to address an Assassin’s need to stock poisons in this way. I decided to point out at the proficiency with the Poisoner’s Kit would apply to those rolls instead of adding in even more proficiencies gained (so no Expertise on those). Do you think I should just give proficiency in Nature, for example?

The Assassin needs to be less of a one-trick pony. I added the bit about crafting with costs halved because this can be an expensive subclass to utilize. Wizards similarly have high costs to their craft as they copy and learn spells; many Wizards halve the costs of copying spells, so I’m borrowing that concept for the Assassin.

I added poison resistance since the Assassin has probably experimented with many poisons and built up immunities. I’m reminded of the duel of wits from The Princess Bride. I like how this will enable the Assassin to be poisoned in a social setting in order to not draw suspicions when others are poisoned (which will be especially important with the level-nine feature).

I thought it needed one more detail to lend the class better to using poisons. Poison damage is debatably the worst damage type in the game; many monsters resist or ignore poison damage. Enabling a character to use poisons won’t inflate damage output beyond reasonable levels. This subclass ought to lean heavier into using poisons anyway since it gains proficiency with the poisoner’s kit.

The bit about Intelligence instead of Charisma is meant to enable the Assassin to focus on Intelligence instead of Charisma. Intelligence will be important for poisons, so I don’t want to split the Assassin between Charisma and Intelligence.

Level 3 – Assassinate [Reworked]

At the 3rd level, your attacks gain advantage against creatures who have not yet taken a turn in a combat encounter. Your attacks become critical hits when hitting creatures who are surprised. You can also add your proficiency bonus to Initiative rolls.

The Assassinate feature is already the popular reason to choose this subclass. I think it just needs this Initiative bonus to lean more heavily into surprising enemies.

An alternative idea for the Initiative bonus is to tie it to the character’s Intelligence modifier (instead of the scaling proficiency bonus). This would make it similar to the Swashbuckler’s Rakish Audacity for Charisma. What do you think is better for improving the Assassin’s initiative rolls? (This suggestion comes from C3Squared on YouTube. I personally prefer the bonus to be tied to the proficiency bonus so it can qualify for Reliable Talent, making Initiative rolls very reliable for the Assassin. I also like to develop other stats for a subclass, though I know WotC is moving away from that method to instead use proficiency bonuses in many new subclasses.

Level 9 – Infiltration Expertise [Reworked]

Starting at 9th level, you gain proficiency with forgery kits. You roll skill checks with advantage to impersonate or adopt fictional personas or impersonate individuals if you observe the subject’s speech, handwriting, mannerisms, or other notable traits for ten minutes.

Poison at night can be as deadly as an army at noon. You roll Sleight of Hand checks with advantage to avoid detection when poisoning food or drink.

The PHB version of this subclass gives you a massive drought of good abilities. Infiltration Expertise and Impostor are bad abilities that make it boring to level up as an Assassin. You can already do most of what those features give you. Any character can attempt to create aliases or impersonate other people. My version combines the best parts of Infiltration Expertise into one ability at level nine. Now you can tear apart an organization from the inside while they argue about who seems suspicious to them.

I added the ability to reliably poison food and drink because I want to lean heavier into the poisoning aspect of the Assassin (as I mentioned earlier). This will give the Assassin more options to take people out after successfully infiltrating a secured location. Going unnoticed after poisoning someone can keep the Assassin alive. Drawing a blade can be messy, so maybe a neater approach is required.

I tried to keep the best parts of the original Infiltration Expertise and Impostor features, but they still don’t excite me. What do you think would jazz up this level-nine feature? I’m considering removing the advantage on Deception to instead just give the Assassin proficiency with Deception if it doesn’t already have it.

Level 13 – Just Business [New]

At 13th level, your Sneak Attack dice become d8’s instead of d6’s. Treat ones and twos rolled on your Sneak Attack dice as if they are threes.

This feature replaces Impostor. I removed Impostor because I worked it into the Infiltration Expertise feature at level nine. I like this change because the Assassin’s damage becomes more reliable without relying on Surprise; however, it further buffs the surprise attack’s damage potential. It’s an overall damage buff as Just Business makes all Sneak Attack damage more deadly, regardless of surprise.

The buff to Sneak Attack dice and the higher damage floor seem like a worthy but tempered change. I think more Rogue subclasses should mess with Sneak Attack as the Phantom Rogue does. Sneak Attack is a core class feature that I enjoy, so I like the idea of it being customized to each type of Rogue. In this case, it does more damage.

The damage increase per Sneak Attack die is 1.375 on average. At level thirteen, that’s an average damage increase of 9.625 per turn (calculations are only based on damage, not chances to hit and other considerations). It raises the damage range of Sneak Attack at level thirteen from 7-42 to 21-56. If I were to keep Sneak Attack dice as d6s, the range would be 21-42. The range at level nineteen would increase from 10-60 to 30-80. Damage range numbers can be doubled when assuming a critical hit.

All in all, my revision gives Sneak Attack damage greater potential and more reliable minimums. I could be persuaded to believe that it’s too drastic, but I’m inclined to stand by it, for now, considering the sad state of the Assassin by RAW. I believe this damage increase can make you feel like an Assassin even when you’re not rolling critical hits with Assassinate on surprised enemies.

Rogues are also notorious for wanting to multiclass at higher levels because they don’t gain much. I want this revision to break that trend with Just Business at level thirteen. That’s a high enough level that you really start feeling like you’re left in the dust by spellcasters, so a power boost like this seems welcome if I’m playing an Assassin. Just Business also provides an incentive to level up for more Sneak Attack dice per attack since the damage becomes more reliable and the minimum and maximum damage potentials shift upward.

If this feels like too much damage to you or your DM, you can tone it down in a few ways. Mix and match these three methods for the right fit to your game: (1) keep Sneak Attack as d6s, (2) reroll 1s and 2s instead of counting them as 3s, or (3) make the better Sneak Attack a limited resource based on Proficiency Bonus (use super Sneak Attack number of times equal to PB).

Remember, the low-level abilities use poison damage, which becomes increasingly useless at high levels against poison-immune monsters. Without some way to supplement damage, this really is a vanilla Rogue with no subclass at high levels (*sad Assassin face*).

Level 17 – Death Strike [Reworked]

At 17th level, you master the art of killing or crippling enemies. When you attack and hit a surprised creature, it makes a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). Double the damage of your attack against any creature that fails this saving throw. Regardless of whether the creature passes or succeeds at this saving throw, its Initiative value in the turn order is reduced by 2d6 + your Dexterity modifier for the remainder of the combat encounter.

I love Death Strike, but it does nothing for you if the target succeeds on its saving throw. This signals to me that Death Strike needs a secondary effect. As I’ve mentioned with previous features, Initiative rolls are a focus of the Assassin. I’m going to lean on that need. The entire party benefits from a prominent enemy being last (or close to it) in the turn order. The target will still be surprised as the Assassin’s allies finish what was started, so they can attack with advantage and get into position. I don’t imagine that target will last the round.

This change means the Assassin can still feel cool and be celebrated by other players if Death Strike doesn’t deal double damage. Now the party will be equally invested in helping the Rogue to surprise the enemy.

Change Log

I’ve received amazing feedback from our YouTube channel, prompting several changes to my revision to improve it. Here are changes I’ve made to the revision based on your gracious feedback:

  • Specified that proficiency with the Poisoner’s Kit can apply to Nature and Persuasion checks (for example) that are made to obtain, identify, or harvest poisons. This is a quality-of-life change so it’s easier to understand poison mechanics; it doesn’t add anything new from RAW.
  • Organizationally changed some of the level-three features so the Initiative bonus is tied to Assassinate and the poison bonus action is tied to Tricks of the Trade.
  • Death Strike’s reduction to Initiative is 2d6+Dex subtracted from the target’s Initiative, instead of just setting it to 1.
  • Tricks of the Trade allows Intelligence to be substituted for Charisma in skill checks based on Charisma.
  • Simplified level-nine Infiltration Expertise to be consistent with the updated Tricks of the Trade.

Thank you to all of you who have provided amazing feedback here in the comments or in the YouTube video comments!

What Do You Think?

I’m happy with this version of the Assassin. It’s my second draft after much consideration. My first character started out as an Assassin until D&D 5e exited the playtesting phase and officially released the Arcane Trickster. I had heaps of fun trying to assassinate enemies, and my DM was very accommodating (perhaps too much in hindsight). I hope my revision of the Assassin will help someone like you to enjoy playing it more than the PHB version.

Tell me what you think of it, please! I may alter my version based on your feedback. I’d like to hear about any other revisions you’ve made or discovered to the Assassin. Use Cunning Action to Dash to the comments section at the bottom of this page to discuss the Assassin before it discusses us…

You may enjoy these other articles that Opal and I have written about Rogues:

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For DnD 5e, assassins are ambush masters with quick, deadly efficiency and masterful infiltration skills.  This subclass is probably the best suited for combat as a rogue, utilizing the rogue’s Sneak Attack against enemies with a slower initiative.  No need to hide if I’m faster than my opponents off the jump.  Plus, the added proficiencies with the disguise kit and poisoner’s kit can offer fun options to the game.

When making an assassin character for Dungeons and Dragons 5e, consider the following:

  • Choose a race with high Dexterity modifiers
  • Think about backstory—hired killer, agent, sacred priest
  • Build rogue for combat—Sneak Attack, Expertise, Cunning Action
  • The assassin role—Assassinate, Infiltration Expertise, Imposter, Death Strike
  • Utilize higher-level rogue abilities—Uncanny Dodge, Evasion

Choose a race with high Dexterity modifiers

The assassin thrives on a high Dexterity score—attack and damage rolls, AC, Stealth.  Therefore, I want to pick a race with the highest Dexterity modifiers and perhaps a few bonus abilities.  The best three races that come to mind are tabaxi, high elf and feral tiefling.

Tabaxi are cat-like people—often jaguar or leopard—who get a +2 Dexterity/+1 Charisma bonus combination.  Our assassin could be a jet-black panther bounty-killer who stalks his prey like a ranger.  This feline race also benefits from natural abilities like Feline Agility, Cat’s Claws and Cat’s Talent.  Therefore, I have natural speed, stealth and hand-to-hand combat options that would come in handy as a hired killer.

A high elf assassin would be an interesting—yet effective—choice.  With a +2 Dexterity/+1 Intelligence bonus combination and a free cantrip, I could build this rogue as a wizard hunter.  The cantrip I’ll choose is minor illusion, giving me the ability to distract a target as I sneak in.  Plus, I’ll gain proficiency with a longbow, increasing my damage output on ranged attacks.

On the other hand, feral tieflings could offer a variant on this wizard hunter with a +2 Dexterity/+1 Intelligence bonus combo.  However, I’ll replace the cantrip with inherent tiefling spells from Infernal Legacy.  When I become an assassin at level 3, I’ll also gain the hellish rebuke spell.  Now, if I fail to finish my target with the initial strike, I can engulf my foe in 3d10 fire damage.  I’ll need to rest between uses.

Think about backstory—hitman, agent, sacred priest

Playing an assassin comes with options.  So, figuring out a cool backstory and motivation can bring this dark character into the group.

A hitman could begin the campaign as a nefarious character, learning how to accept a better way of life with friends.  I could play this character as an anti-hero—it’s built into the story unless I’m playing a campaign to destroy do-gooders.  Remember to ease up on the bad guy throttle and try not to be a stick in the mud.

An agent would be a more restrained version of this deadly class, working in tandem with a kingdom or guild.  This agent could lean on the infiltration aspects of the assassin, using martial prowess only when necessary.

The sacred priest concept is one of the more exotic options for the assassin, acting as lethal agents who vanquish foes of a certain deity.  My previously mentioned wizard killers could fall under this umbrella, eliminating those who dabble in the dark arts.  This priest could bring punishment to those who break some sort of wizard law.

Build rogue for combat—Sneak Attack, Expertise, Cunning Action

My first-level rogue should utilize a rapier or katana for lethal combat damage.  A burglar’s pack and a proficiency in thieves’ tools will offer me basic rogue equipment.  I’ll also choose Stealth as a proficient skill—something I’m bound to use often.

As an early-level rogue, I’ll be able to use an assortment of abilities.  Sneak Attack, Expertise, Thieves’ Cant and Cunning Action are my rogue staples.

Sneak Attack grants me an extra 1d6 damage when I have advantage on the attack.  Of course, this damage grows quickly as I level up and becomes crucial for my assassin role.  By the time I choose this subclass, my Sneak Attack damage will be at 2d6 damage.

Expertise doubles my proficiency bonus for skill checks and thieves’ tools.  This means my ability to disarm traps and pick locks is largely increased.  My Stealth will also be enhanced with this bonus, giving me better opportunities for Sneak Attack damage.

Thieves’ Cant is a secret language between rogues.  As an operator of the underworld, rogues communicate with one another through signs and whispers.  I’ll be able to move through criminal elements in the towns I visit.

Cunning Action offers bonus action options—Dash, Disengage and Hide.  The idea is to increase my maneuverability and give me opportunities to keep using Sneak Attack.  Extra movement and the ability to disengage enemies are crucial for my combat survival.  Honestly, this character is more of a glass cannon.  So, don’t forget to move!

The assassin role—Assassinate, Infiltration Expertise, Imposter, Death Strike

When I reach level 3, I’ll gain my first two crucial Assassin abilities: Assassinate and Bonus Proficiencies (poisoner’s kit, disguise kit).

Assassinate adds to the rogue’s basic Sneak Attack ability, granting a critical hit with bonus damage dice on slower opponents.  Whenever I attack an enemy who has not yet taken a turn, I gain advantage on the attack along with a critical hit.  Now, I’ll be able to add the extra 2d6 (at level 3) damage on top of the critical hit weapon damage.

My Bonus Proficiencies with the poisoner’s kit and disguise kit open gameplay options in interesting ways.  One part of the Assassin’s role is to be an infiltrator—and, frankly, we can get Scooby-Doo-level silly with these disguises.  Poison offers a unique damage option after the initial blows are exchanged, often adding extra 1d6 damage on failed Constitution saves.

Infiltration Expertise (level 9) and Imposter (level 13) are the next two abilities I learn, leaning into my disguise kit.  Infiltration Expertise allows me to create a fake identity for myself, established over several days.  Then, Imposter allows me to recreate another person’s voice, handwriting and behavior.  Though the idea here is to get to a target and eliminate that person, I could repurpose these abilities for all kinds of creative uses.

Death Strike is my ultimate move, forcing opponents to make a Constitution saving throw or take DOUBLE my already critical attack damage.  At level 17, this includes 9d6 Sneak Attack damage.

Utilize higher-level rogue abilities

At higher levels, my assassin will learn a list of cool rogue abilities that will enhance my combat and role in the group.

  • Uncanny Dodge allows me to use my reaction to half melee attack damage against me.—Level 5.
  • Evasion grants me the ability to take 0 damage on successful Dexterity saving throws for magical area effects. Normally, this would be half damage—Level 7.
  • Reliable Talent allows me to treat a d20 skill check of 9 or lower as a 10. Therefore, I can’t roll anything less than a 10 before adding my modifiers. This only works for proficient skills—Level 11.
  • Blindsense gives me the ability to sense creatures within 10 feet of me when in total darkness. This will come in handy if I need to do any real assassination missions. Level 14
  • Slippery Mind gives me proficiency with Wisdom saving throws. This defensive bonus will keep me from falling into charm or fear—Level 15.
  • Elusive negates advantage on enemy attack rolls. Therefore, I’ll keep my edge in quick maneuverability.  Level 17
  • Stroke of Luck grants me an automatic hit when I miss.  This goes for combat or saving throws, needing a rest between uses.  Level 20.

To Sum it Up

The Assassin has a mixture of roles within a party: lethal damage dealer, trap finder and infiltrator.  This character is the party’s ninja, skulking in the darkness to cover our flank and root out ambushers.  Utilizing a finesse sword (shortsword, rapier, katana), I can increase the effectiveness of my Assassinate ability.  Plus, the poisoner’s kit can add a unique effect to my ranged attacks.

My roleplaying options are varied, but definitely on the darker side of character development.  One of my favorite hooks is the wizard hunter.  I could tie this into the story in interesting ways and play a half elf or feral tiefling.  Plus, my poison is more likely to work on these enemies—as opposed to undead or supernatural beings.

Categories Dungeons and Dragons 5e, Fantasy, Role PlayingTags build swordsman, character build, character builds, dark fantasy, dnd 5e, fantasy role play, ninja, ninja character, rogue, swordsmanSours:

Source: Player's Handbook

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and the poisoner's kit.


Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

Infiltration Expertise

Starting at 9th level, you can unfailingly create false identities for yourself. You must spend seven days and 25 gp to establish the history, profession, and affiliations for an identity. You can't establish an identity that belongs to someone else. For example, you might acquire appropriate clothing, letters of introduction, and official- looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.

Thereafter, if you adopt the new identity as a disguise, other creatures believe you to be that person until given an obvious reason not to.


At 13th level, you gain the ability to unerringly mimic another person's speech, writing, and behavior. You must spend at least three hours studying these three components of the person's behavior, listening to speech, examining handwriting, and observing mannerisms.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

Death Strike

Starting at 17th level, you become a master of instant death. When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.


5e assassin

assassin 5E

The traditional example of the Sneak Attack. The reason rogues have the feature. The knife in the dark, and the master of surprise. The Player’s Handbook introduced the Assassin as a being who eliminates whatever target they are asked to by any means necessary. You might be a mere bounty hunter, or a tribesman who needs to destroy a life to prove themselves. Either way, you have a unique set of skills that are useful for any adventuring party. Let’s take a gander at them through our Assassin 5e Guide.

Master of Disguise: Assassin 5E

The Assassin has absolutely ridiculous flavor. This rogue archetype has two aggressive abilities focused around killing someone before they can even scream. They gain two features that help you get the jump on people. The aggressive abilities are absolutely incredible and make your party focus around stealth and shock. The other two features are… somewhat weak, and require very specific intrigue campaigns to work.

Bonus Proficiencies

Before you get any class features, an assassin needs to have the tools to succeed.

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and the poisoner’s kit.

The fact that you don’t get skills to help you here is somewhat unfortunate.

Disguise kits are flavorful and not bad at all! With their help, you can pretend to be quite a few things. If you’re a small assassin, you can pretend to be a lot of common enemies (including Medium ones if the GM let’s you on stilts!). You can start combats in a lot of interesting and unique ways by simply stabbing someone who willingly makes friends with you. The most common Disguise skills involve Intelligence or  Wisdom to make the disguise, and Charisma checks when things go wrong (Deception). Try to bend the field in your favor by doing actions that use your Proficient and Expertise skills.

The poisoner’s kit is less common, but still quite useful. There are, sadly, a lot of things that are immune to poison. If you need to fight Undead in your near future, or constructed beings, then make sure you don’t waste your stuff. Otherwise, go wild! Checks to craft and apply poison to your weapons are GM discretion. Your best bet is probable Intelligence to craft, and Dexterity to apply. 

Both of these kits lean towards decent Intelligence scores and then relying on your Kit proficiency to create what you need. You’ll have good Dexterity by default. Charisma might be good for when your disguise is ineffective, or your poison doesn’t take hold.


This is your first strictly offensive ability (unless you count the Poisoner’s Kit!). It’s also pretty decent!

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

If a creature is surprised, they haven’t acted in combat yet. That means you have advantage to score an automatic critical hit. That’s amazing!

And then combat begins in earnest.

So, what’s the best usage of this ability? First, you’ve gotta identify what the threat on the battlefield is, or someone who’s completely alone. If you can take out a scout before they notice you, then you’ve got a free surprise round, and you can refresh Assassinate for the next fight. Your goal is to try and stab them to take them out, and maybe have an Archer or Caster finish the job. 

In big fights with multiple creatures, you’re going to want to become as stealthy as possible. If you can, make Stealth your Expertise, and get to the backlines of the enemy team. Then, you can start a fight by auto-critting the enemy’s caster, potentially taking out a major threat before the battle even begins.

You may want to consider being focused on ranged combat. Especially later on, when enemies get Truesight, you’ll want to just out-range their ability to see you.

Get the jump on combat, preferably with an ally or two that focuses on stealth. Then, you can remove major problems before they even begin.

Infiltration Expertise

After 6 levels of getting the jump on your enemies, you get something that might help you in intrigue scenarios. An assassin gets this at level 9.

You must spend seven days and 25 gp to establish the history, profession, and affiliations for an identity. You can’t establish an identity that belongs to someone else. For example, you might acquire appropriate clothing, letters of introduction, and official- looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.

Thereafter, if you adopt the new identity as a disguise, other creatures believe you to be that person until given an obvious reason not to.

This isn’t bad. Really! But it requires two things to work at all.

First, the scenario must arise. You must be in a situation where you can have a week to learn about and join a society or social group. And that has to be useful for you or your party in some variety. Usually, getting a possible identity established is good for you so you can sneak into parties and whatnot. But, that week timeframe is dangerous. Your GM decides how active you have to be during the time, so you might be able to do other things in the background. But, if the party is in 3 days, then you’ll just have to disguise the old-fashioned way.

The other important thing is that your party would have to be willing to wait that long. If you don’t have a party that wants to rush things, you can more often spend the time to get identities in every town you go to. That gives you a wide assortment of identities that you can swap to when needed. Then, creatures (not just townsfolk!) have to believe you until proven otherwise.

If you get both of these qualities, you can have a legitimately good method of gathering disguises that creatures can’t roll against. You’ll be an essential part of intrigue scenarios, and have multiple methods of using Deception to your advantage.

However, if both of these situations aren’t around, then you might be in some trouble. You’ll have to deliberate with both your party and GM by level 9 to see if it’ll work with everyone involved.


Then, you get increasingly more abilities to help you sneak into situations. This one takes less long, but allows for natural saves.

At 13th level, you gain the ability to unerringly mimic another person’s speech, writing, and behavior. You must spend at least three hours studying these three components of the person’s behavior, listening to speech, examining handwriting, and observing mannerisms.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

Three hours is still a long time, especially if you want to disguise as a bandit or servant of an undead master. But, if your party lets you work, you can get some value out of this. You can watch a scout’s mannerisms and speech as they walk around an area. Then, you can Assassinate them and take their identity, allowing you to gather information for your party as you return and talk to your new allies.

Of course, a similar scenario can be applied to actual intrigue situations. If there’s someone that has a party invitation that finds themself alone, then surely you could take their place. Over three hours of watching them, and enough Intelligence (History) checks, you might get good enough small talk to avoid raising suspicion.

However, you still have the same problems as before. 3 hours is a long time, so if you have harsh deadlines, you can’t use this. And if your party just wants you to shut up and Disguise kit your way in there, you probably should to avoid frustrations. Try to only take this archetype with a calm party, if you want to make use of this stuff.

Death Strike

It only took 14 levels, but it’s finally time for the Surprised aspects of your class to shine through once again!

Starting at 17th level, you become a master of instant death. When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.

That’s pretty awesome! On your typical rogue, you’ll be at 20 Dexterity with a +6 Proficiency bonus (without magic items!). DC 19 isn’t too easy for most creatures to succeed at, and with magic items you’ll be likely to have DC 20-21. That’s a huge chance to double your attack…

And then critically hit! That’s 4x the damage!

So, on surprised creatures, you get advantage on the attack roll and your attack hits for 4x the damage. That’s absolutely bonkers! You’re essentially basically hitting someone for 40d6 by level 19, something a caster could only dream of doing. And that’s just through class features! I’m not even considering weapon enchantments, Dexterity modifier, or anything connected. That’s an insane amount of damage! Even in the super late-game, very few enemies will be able to tank that hit and still be in great fighting shape.

The first round will be crucial for you. You’ll almost need to one-shot an enemy to be doing your job. After the really impressive first hit in a round, you… kinda just become a rogue without an archetype. You better make sure that your hit takes someone out! Not that that’ll be hard; if you get the jump on someone and they fail the Death Strike saving throw, you’ll one shot really powerful beings, like Liches.

Best Race for Assassin Rogues

Assassins need Dexterity; stealth and landing attack rolls are essential for your job as taking someone out immediately. Afterwards, your Charisma should probably be at a place where it’s not embarrassing if you get caught out. You don’t wanna be rolling a -1 when you’re caught in a disguise! Of course, if you don’t mind making Deception an Expertise, you’ll be fine with low Charisma.


While Kobolds may be one of the weakest races introduced in Xanathar’s Guide to Everything, they still make for excellent rogues. Dexterity is all you really care about for being an Assassin, and while you’re graced with a -2 Strength penalty (for some reason), you’re probably just fine with 6 Strength.  Pack Tactics is easy advantage on attack rolls, and you’ll be happy with Groveling if an assassination attempt goes wrong. Light Blindness is a chore to work through; if your GM is kind, consider asking them for the equivalent of sunglasses for yourself, or just use Pack Tactics to work your way through it.

Being naturally small is good for identities. It lets you have a wider range of size options to easily disguise yourself on. Just make sure your Disguise Kit has some stilts.

Lightfoot Halfling

If you’re looking for something relatively simple, then Lightfoot halflings are for you. +2 Dexterity is what you’re wanting, and +1 Charisma is just fine. Lucky’s wonderful for you, as is Nimble. Hiding behind the Fighter is just a good idea; you could have a Paladin talk to an enemy while slowly getting closer to them, and then get the drop on them while they’re surprised! Unfortunately, it’s insanely difficult to get Surprise more than once in a combat. So… just make good use of your allies’s shadow.

A Consideration: Human

Humans aren’t bad for you. Even non-variant human allows you to get 14s in all stats, making you good at skills. And Variant Human allows you to pick up Alert and always go first! Not bad, if you want to see the power of Alert and Assassinate.

Conclusion – Our Take on the Assassin 5E

The Assassin is one of the coolest subclasses in the entire game, but suffers a lot from the typical dungeon experience. You get a single attack roll to shine, and then you become archetype-less… if your GM is doing a typical slashing crawler. In social campaigns, Assassins can become incredibly good, allowing you to get access to disguises in perfect situations. If you either don’t mind losing your archetype after the first round of combat, or you’re entering a social campaign, this is a fantastic choice!



The Assassin Rogue in D&D 5e represents that iconic ability of the rogue to quickly and silently take out a high-priority target. These characters strike suddenly and aim to be as decisive in their strikes as possible.

Picking members of a hobgoblin warband off one-by-one, the Assassin lurks in the shadows of the encampment. With her blade gripped firmly, she identifies the next straggler of the group and begins to move silently towards him.

By the time the hobgoblin realizes that he is being attacked, it’s too late. He lets out a single silent whimper as he falls to the ground.

Now only the target remained: the hobgoblin commander who was still asleep in his now-unguarded tent…

This is the Assassin Rogue Guide for D&D 5e.


What is the Assassin Rogue in D&D 5e?

The Assassin Rogue may be a master of disguise who prefers to blend in to their surroundings to get closer to their target.

On the other hand, they may prefer to keep their distance and strike with a decisive shot from a bow or crossbow. Though we can’t forget their talents and notorious preference for poisons…

Ok, so there’s a lot of ways that an Assassin Rogue can use to do their job. Realistically, they are likely to use whatever will best guarantee that they can strike that decisive blow before anyone knows what’s happened.

Whatever approach the Assassin chooses, they are bound to rely on a combination of speed, stealth, and the element of surprise to accomplish their goals.

The Assassin’s Role in the Party

The Assassin Rogue largely fits the typical expectation for a Rogue’s role in the party. They maneuver around the battlefield and strike at enemies when and where they are most vulnerable.

Dealing tons of damage with their trusty Sneak Attack, the Assassin is able to assist their party in making quick work of enemies.

Where the Assassin sets themselves apart is their Assassinate ability, which we’ll go into more detail about in a moment.

Assassins are at their best when the party is able to get the jump on enemies. By setting the Assassin up to be able to strike before the enemy is even aware of the party’s presence, a potentially deadly fight could be over before it even begins!

Otherwise, the party still finds themselves at a major advantage thanks to the Assassin’s bonuses when initiating the combat.

You will want to read our article covering the Surprise mechanic if you’re playing an Assassin Rogue. After all, you’ll be relying pretty heavily on getting the jump on enemies!

Assassin Rogue in D&D 5e Abilities

The Assassin’s abilities are meant to make it easier for the Rogue to get the jump on their enemies. With the element of surprise, the Assassin can take out a threat before they even get a chance to act!

Two of the Assassin’s abilities are amazing at letting the Rogue quickly take out enemies. The others are still very useful, but play to a more intrigue-heavy situation or style of play.

However, whether you’re playing a game with lots of intrigue or not, the Assassin is a powerful ally to have!

Bonus Proficiencies

When taking the Assassin archetype at level 3, your character gains proficiency with the disguise kit and poisoner’s kit.

Disguise kits add a ton of flavor to the game and can be incredibly useful. This is especially true for an Assassin who is looking for a clever way to get close to a target. With a good disguise, some convincing, and a sharp blade, the Assassin can unload some major damage on an enemy before they even get a chance to retaliate.

With a bit of preparation, poisons can be very useful. Applying some poison to your weapon or dropping some in the target’s wine can have some major effects against enemies.

Just be aware that there are several non-humanoid creatures with resistance/immunity to poison. Against enemies that are Undead, constructs, or fiends, you’re better off saving your poison for later.


Additionally at 3rd level, the Assassin gets their “bread and butter” ability.

With the Assassinate ability, the Assassin gets advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. Plus, any hits you score against a creature that is surprised are automatically considered to be a critical hit.

A surprised creature will not have had the chance to act in combat yet. Against a surprised creature, you roll your attack with advantage and get an automatic critical hit if the attack lands.

This is incredible and well worth the time to set up situations where the Assassin can initiate combat to get this bonus.

Getting the Best Value Out of the Assassinate Ability

So how do you maximize the benefits of the Assassinate ability in D&D 5e?

First things first, you want to identify who your target is.

You want to look for what enemy is likely going to be the biggest threat in combat. This might be a wizard that you can potentially drop with a single Sneak Attack.

If it’s a beefier enemy that you can’t one-shot, laying down the hurt before the combat even begins will make them easier for the party to deal with. A spell or arrow from a party member may be all it takes to drop them once you’ve dealt your Assassinate damage!

Additionally, you want to look for any enemies who are isolated. If you can take them out quickly and quietly, that’s one less threat on the field when combat starts. Consider how important action economy in D&D 5e is, even removing one enemy pre-combat can greatly tilt the scales in your favor!

If it happens to be the high-threat enemy that is away from the rest, that’s even better!

If combat has already started and you have multiple enemies, you’ll want to focus heavily on using your Stealth skill. By getting into the enemies’ backline, you can cause all kinds of havoc.

Sneak Attack the stragglers (with advantage for hiding), use your Cunning Action Rogue ability to take cover again, rinse and repeat!

You may also consider ranged combat to give you even more options to maneuver and hide. Hanging just out of the enemy’s sight and using the environment for cover can also be a reliable way of getting to use your Assassinate ability.

Just remember: focus on surprising the enemy and neutralizing threats before they can become a problem!

Infiltration Expertise

At level 9, the Assassin gains the Infiltration Expertise ability.

With this, you are able to create a new identity. This can be very useful for infiltrating certain organizations and getting closer to targets.

After a week of work (and 25gp), you have a new identity complete with an established history, profession, and affiliations. While you can’t establish an identity that belongs to someone else, your new identity is so well-crafted and convincing that others will believe you to be that person unless you give them an obvious reason not to.

As one would expect, this works best in campaigns with lots of intrigue. Having to take a week for all of the preparation and work necessary to create the identity may not vibe in certain situations. Your party will need to be ok with taking a week to do other things while you create the identity.

Furthermore, if you are needing the identity to infiltrate an event that is in less than a week, you won’t have enough time to prepare.

If your party is fine with hanging out for a week and you have time to create your identity, it can give you some interesting options on your adventure. It is fully possible to have a different identity in every town or city that you visit!

Because creatures can’t roll against your identity like they might roll against a disguise, this can be a very reliable infiltration tool that is worth the time and gold to create!


The Assassin’s level 13 ability adds to their effectiveness in all things espionage.

By spending at least three hours studying a person’s behavior, the Assassin can perfectly mimic that person. This includes their speech, behavior, and handwriting as long as all three have been observed.

The casual observer will not be able to tell a difference between you and who you are impersonating. Someone who suspects something may look closer, but you still get advantage on any Charisma (Deception) check you make to avoid being detected.

As with the Infiltration Expertise ability, this works best if you coordinate with your party. Being able to observe a guard captain, for example, gives you the information you need to impersonate them. Assassinating them and taking their identity as cover would give you free reign to explore and provide valuable recon information to your party.

Nevertheless, this ability relies on your party agreeing to a plan that makes use of your skill. If they would prefer to storm the base instead of just sitting there while you do recon work, it may be better to stick with the majority to avoid frustrating other players.

Death Strike

Finally, at level 17, the Assassin Rogue gets the Death Strike ability.

With this ability, a surprised creature that the Assassin hits with an attack must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). If the creature fails this saving throw, the attack’s damage is doubled.

Generally speaking, a level 17 Rogue will have a Dexterity score of 20 and a proficiency bonus of +6. This means that the DC is 19 unless you have any magic items that would make it more difficult.

So because the creature is surprised, you are attacking with advantage. Your Assassinate ability means that the attack will automatically result in a critical hit, which doubles the damage dice. If the target fails their save, the damage doubles again from Death Strike.

So at level 17, you’re looking at:

(Crit Weapon Damage x2 + Dexterity modifier + Crit Sneak Attack x2) x 2

Let’s say you’re using a rapier and have a Dexterity score of 20. You hit and the target fails their save against Death Strike. It would look like:

(2d8 + 5 + 18d6) x 2

For an average damage of:

(9 + 5 + 63) x 2 = 77 x 2 = 154 DAMAGE!?!?!?!

(Just for laughs, it would mean a maximum damage of 258 in this example.)

This is enough to drop most enemies in a single hit. If they’re still standing afterwards, they will not be in good shape!


In many ways, the Assassin is what most players picture when they think of a Rogue. Only the Thief archetype is potentially more iconic to the base class.

This means that there is absolutely no shortage of sources for inspiration when connecting your Assassin Rogue to the game’s world.

The most classic example is that of a Bounty Hunter.

They might be a member of a guild or organization who specialize in fulfillment of certain contracts. If this feels too morally gray, the organization may only accept contracts for justified killings with full approval from the authorities.

On the other hand, they might be more accustomed to life outside of an organization. They might be more of the lone wolf type or may be most comfortable in a small group.

Any Assassin is bound to be resourceful and, with their knack for intrigue supporting them, it’s fully possible that they might have numerous backstories and reasons to join the party.

Is the Assassin Rogue Archetype Good?

The Assassin can put out some incredible damage. The Death Strike ability does a lot to help the archetype stand out in the late game.

For the Assassin, the value is mostly packed into that first strike. After dealing a ton of damage to initiate combat, the Assassin doesn’t particularly have many extra abilities to rely on that aren’t available to all Rogues.

To really shine as an Assassin, it’s worth taking some time to coordinate tactics with your team. If you just leave it up to the initiative rolls, you’ll basically never get to use your abilities to their full effect.

These conversations can certainly be had in-character to add to the roleplaying of your game. If you have a plan and pitch it well to the party, they’ll be more likely to go along. If you don’t communicate these goals, you’ll be fighting an uphill battle.

Speaking of which…

Injecting intrigue and spycraft into a campaign can be fun, but it relies on everyone at the table wanting to play that kind of game. Otherwise it gets boring and frustrating in a hurry.

It might be incredibly fun for the Assassin to create their disguise, do a bunch of recon and fully explore a location, possibly make time for some sabotage, then come back and report what happened. But all the while, the other players at the table are rolling their eyes, scrolling Instagram, or anything else.

If you aren’t playing a game with lots of intrigue, it will be very difficult to get value out of your level 9 and level 13 abilities. That may be important to you or you might not particularly care.

Either way, it is something to consider before choosing this archetype.

Consider what type of players are at your table!

(Pssst… we talk about the different types of players in this article that you should check out!)

Conclusion – The Assassin Rogue in D&D 5e

Assassins are at their best in the first round of combat or in a campaign with lots of social interactions.

With the ability to deal crazy amounts of damage and blend into any crowd, the Assassin is a subclass that’s got both flavor and function.

With some planning and coordination, you won’t just be a high-damaging shadow filling your enemies with paranoia and dread: you’ll look good doing it.

That said, if you’re looking at playing an Assassin, you’ll definitely want to check out my Complete Guide to the Rogue in 5e!

If you want to learn how to get the most out of your Rogue’s Sneak Attack ability, you’ll want to check this article out!

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Trained in the use of poison, assassins are remorseless killers who work for nobles, guildmasters, Sovereigns, and anyone else who can afford them.


Assassinate: During its first turn, the Assassin has advantage on Attack rolls against any creature that hasn't taken a turn. Any hit the Assassin scores against a surprised creature is a critical hit.

Evasion: If the Assassin is subjected to an Effect that allows it to make a Dexterity saving throw to take only half damage, the Assassin instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.

SneakAttack (1/Turn): The Assassin deals an extra 13 (4d6) damage when it hits a target with a weapon Attack and has advantage on the Attack roll, or when the target is within 5 ft. of an ally of the Assassin that isn't Incapacitated and the Assassin doesn't have disadvantage on the Attack roll.


Multiattack: The Assassin makes two Shortsword attacks.

Shortsword: Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 6 (1d6 + 3) piercing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.

Light Crossbow: Ranged Weapon Attack: +6 to hit, range 80/320 ft., one target. Hit: 7 (1d8 + 3) piercing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.

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Thieves' Cant Plus Any Two Languages

Saving Throws


Acrobatics +6, Deception +3, Perception +3, Stealth +9

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