Complete Guide to Playing an Assassin Rogue in 5e D&D
Dropping the hammer as a 5e Assassin feels good! If you’re with the kind of group who love to carefully plan out their operations, playing this Rogue subclass can be a satisfying experience. A master of stealth, disguise, languages, and assassination, the 5e Assassin is as deadly as they come.
Some will tell you the DnD 5e Assassin is a one-trick pony. Honestly, there’s a grain of truth to this. But it doesn’t do justice to how much fun executing that deadly trick is. Stalking slowly towards the biggest party threat in perfect silence and then crushing that threat in a flash of lethal violence is a fun gameplay loop.
And there’s more to the Assassin than their heavy-hitting Assassinate ability. Along with their base rogue skills, this subclass has enough potential for a variety of gameplay scenarios through their bonus proficiencies, Infiltration Expertise, and Impostor ability. Getting close to your quarry requires different skills than their execution, after all. Let’s quietly and expertly roll up a 5e Assassin.
How to Use This Guide
Everything in this guide has an emoji, ranking how useful a given ability or feature is to playing this class effectively.
✅ — An absolutely crucial feature. Often forms the backbone of a class’ look and feel. Will provide some bonus that can’t be found through other means.
🆗 — A solid feature that does its job well. Not game-breaking, and certainly replaceable, but a strong choice that shores up some weakness.
⚠️ — A debatable choice. Could work for a specific build, but otherwise is either a wasted opportunity or is just weaker than other alternatives.
⛔ — Outright bad and detrimental. This weighs down the class and just takes up space on the character sheet. A weakness you will have to accommodate for.
These rankings are meant to help you create an optimized class build, but remember DnD isn’t a game where you need to win to have fun. Weaker but flavorful builds also have their place and can make for fulfilling characters.
How To Play An Assassin
Singular Vision?
Let’s face it, playing an Assassin means you (might) get the biggest potential damage output from any single attack via the Assassinate ability. It’s OK if that’s enough to have you on board. Thankfully, there’s more to this iconic subclass for those who need versatility – just enough, that is. We don’t hesitate to recommend the Assassin. It’s a killer subclass (sorry – haha!), but there’s not nearly as much versatility as some of the other rogue archetypes.
Heavy Hitter
Assassinate can be a game-changer, regularly clearing out the biggest threat to the party in that first, single attack. This feels great. Contributing to the party’s success in such a visceral and direct way always feels good. Giving advantage on attack rolls against creatures yet to take a turn in combat and a critical hit to a creature that’s surprised, Assassinate has the ability to turn the tables in the party’s favor. But for many Assassins out there, it’s the setup before the kill that’s the real fun. Think recent iterations of the Hitman series for inspiration. These players enjoy a sandbox environment with many moving parts and lots of possibilities to exploit. In the right game, Assassins can be a fun subclass outside of their one big combat ability.
Infiltration, Impersonation, And Deception
Though overshadowed by their eponymous ability, the Assassin has more subtle skills in their arsenal. They’re proficient in disguise and poison kits and gain additional dedicated infiltration skills at higher levels. This subclass is a linguist, a capable spy, an excellent mimic, and can forge the paperwork and documentation needed to deflect suspicion. All of this makes for serious utility in social situations and encourages you to build a character with Charisma for when stealth fails or someone becomes suspicious of your cover. Talking your way out is often preferable if it brings you closer to your target.
🥷 Player Tip: Ask your DM – You Never Know
The Assassin’s document forgery ability is a good example of a gameplay mechanic that’s fairly open-ended. As a DM, I’d be liberal in my interpretation of what the Assassin is capable of producing if their ideas could lead to interesting scenarios. Asking the DM if you have a suitable document after it’s demanded of you from the city guard probably won’t work. Before attempting infiltration, brainstorm what you might need with the party.
Assassin Subclass Features
While we’ve established that the Assassin isn’t the most versatile subclass, its limited abilities do synergize well with their base class. Having stealth on your side helps when your best chance lies with lining up a perfect initial shot. Assassinate remains your go-to combat showpiece as you level up. And it’s the introduction of new and exciting ways to go behind enemy lines and get closer to the mark that keeps players coming back.
The problem is abilities like proficiency with the disguise kit, Infiltration Expertise, and Impostor don’t come into play at every session and feel underwhelming to some players. Ultimately, there is enough here for a fun-to-play, mechanically sound character. But how well it works in practice depends on your playstyle, group, and DM.
Level 1 (Rogue)
✅ Sleight of Hand
Use this Dexterity-based ability any time you attempt to plant something on someone, pick a pocket, or conceal an object.
✅ Expertise
This allows you to choose two skills you’re already proficient in and double your proficiency bonuses for those skills. Alternatively, you can choose one proficiency and your thieves’ tools and double those bonuses.
✅ Sneak Attack
Once per turn, you can deal an extra d6 damage to a creature you’ve already hit, as long as you have advantage against that creature. You don’t need advantage if there’s another hostile creature within 5 feet of the target. This includes members of your party, and encourages the Assassin to team up with a melee fighter to focus down enemies.
🆗 Thieves’ Cant
You share a kind of rudimentary language with other thieves and rogues. This form of communication is a little clunky and takes four times longer than common speech to relay a message. Only creatures who know thieves’ cant can understand it.
Thieves’ Cant also has a basic written component, allowing you to produce and discern markings that point to danger, safe houses, stashes, and the presence of fellow rogues.
Level 2 (Rogue)
✅ Cunning Action
This ability allows you to take a bonus action on each turn of combat and use one of these three abilities:
- Dash lets you cover twice as much ground as usual.
- Disengage allows you to disengage from melee combat without provoking an Opportunity Attack.
- Hide gives you a chance to disappear from enemy sight, potentially gaining another chance at Sneak Attack.
Level 3 (Assassin)
✅ Assassinate
This is your trademark attack, giving you advantage on rolls against any creature that hasn’t taken a turn in combat yet. In addition, any attack you land on a surprised creature is converted into a critical hit.
Note: Enemies must be surprised for Assassinate to do critical hit damage. This means it only works one initial time. On first reading the rules for this ability, it may seem like you’ll be landing massive attacks regularly. Technically, when the Surprise rule is played as written, a creature is only surprised when unprepared for combat. After the first exchange in battle, this ability only grants you advantage on attack rolls against creatures that haven’t taken a turn in combat yet – no crits.
✅ Bonus Proficiencies
You gain proficiency with the poisoner’s kit and the disguise kit, giving you tools to get close to your target before striking.
Level 5 (Rogue)
✅ Uncanny Dodge
You’ve become so fast you can react to any incoming attack from a visible opponent. This halves the damage of the attack.
Level 7 (Rogue)
🆗 Evasion
This represents your heightened senses and reaction times. When making a saving throw against an area of effect attack, you don’t take damage if you pass a Dexterity saving throw and half damage if you fail. Stacks with Uncanny Dodge
Level 9 (Assassin)
🆗 Infiltration Expertise
By spending one day and 25 gold, you can create false identities for yourself, including documentation, disguises, and appropriate clothing. This doesn’t allow you to pretend to be another living person but is useful for infiltration.
Level 11 (Rogue)
✅ Reliable Talent
Even when you’re having a bad day, you’re still pretty good at what you do. Now, when you roll a 9 or lower on the d20 for a skill or tool you’re proficient in, it’s automatically turned into a 10. For an Assassin Rogue, this will help with reliably picking locks and disarming traps.
Level 13 (Assassin)
✅ Impostor
After observing or interacting with a creature for three hours, you can perfectly mimic their speech pattern and accent (as long as you share a language). This synergizes with your disguise kit proficiency and Infiltration Expertise, helping you talk your way out of trouble when suspicions are aroused. You gain advantage on Charisma rolls to avoid detection.
Level 14 (Rogue)
🆗 Blindsense
You can now sense illusions and invisible creatures within 10 feet. This helps prevent magically disguised creatures from gaining advantage on attack rolls against you.
Level 15 (Rogue)
🆗 Slippery Mind
This gives you proficiency in Wisdom throws and represents your years of firsthand experience.
Level 17 (Assassin)
🆗 Death Strike
This is an extension of your Assassinate ability. When you hit a creature that’s surprised, the creature must make a Constitution saving throw. A failed save leads to double damage on your attack roll.
Level 18 (Rogue)
✅ Elusive
Your rogue fighting skills have become sharper over time. As long as you aren’t incapacitated, you can no longer suffer disadvantage on attack rolls against you.
Level 20 (Rogue)
✅ Stroke of Luck
Once per long rest, you can turn a miss on an attack roll into a hit, or any failed ability check into a 20.
Player Tip: Don’t Be Afraid to Experiment
We mentioned some players feel the Assassin is lacking features outside of their trademark shot. There are loads of homebrew solutions to take inspiration from. This one from Flute’s Loot is a good place to start for some mechanical and gameplay variety. Check it out once you’re familiar with the standard variety.
Getting the Best From Your Assassin
Your character depends on their ability scores (in addition to the luck of the dice) to determine their success or failure at ability checks. Rogues need Dexterity to dart in and out of range, find cover, and move with speed and timing to leave their opponents breathless. This remains true for the Assassin’s governing mechanics of stealth, sneak attack, and lockpicking/trap disarming as a rogue subclass. Getting into position stealthily and attacking with your ranged or finesse weapons are all influenced by your Dexterity score.
The Assassin’s success in the more covert part of their work depends on Charisma. This character can forge documents, create disguises, and commission outfits to support an assumed identity. They use their Charisma to back these deceptions up with flawless language skills, accents, and speech patterns. There’s as much fun to be had (for some players) exploring this part of the Assassin subclass as there is in dealing that heavy damage.
These two components of the Assassin’s abilities synergize around Assassinate. Using your disguises, documents, and Charisma, you can get close to a target without arousing suspicion. This means when you deliver the first blow, your target is surprised, gaining you a critical hit and potential one-hit-kill.
Player Tip: Look at the Background
Many of DnD’s archetypes have roots in historical reality. And some of these historical tales contain inspiration for character creation and background – perhaps none more so than the Assassin. Though some of Marco Polo’s entertaining accounts of them were fanciful, the real story of the Old Man and the Mountain and his army of fanatically loyal warrior assassins is fascinating. These trained killers would spend months, even years at times, gaining trust to get close to their mark. When sure of success, they’d execute in the most public way possible, then fight savagely to the death, never surrendering. This dedication to infiltration and deception, alongside their fanatical loyalty to a guild master steeped in mystery, makes these warrior Assassins rich inspiration for our DnD character backstory.
To learn more about this fascinating sect, check out this article from National Geographic:
Ability Scores
⛔ Strength
This is a dump stat for Assassins. There will be someone else in the party who can take care of the heavy lifting. (Multiclassing to Paladin might create some use for a higher strength stat later)
✅ Dexterity
This is your most important stat as a Rogue subclass, governing your stealth and attacks.
🆗 Constitution
You need hit points. The Assassin, like all rogues, prefers to hit without getting hit in return. But eventually, you will take damage.
⛔ Intelligence
This is a dump stat for your Assassin.
🆗 Wisdom
Wisdom (perception) can be useful to rogues during exploration, especially if you are the party’s chief scout.
✅ Charisma
The Assassin’s non-martial skill set depends largely on their Charisma. You need some points in this ability score to help with deception and “social stealth.”
Racial Considerations
Choosing a race that boosts Dexterity and Charisma will help you optimize your Assassin. Sneaking, sniping, dashing, and hiding are informed by your Dex score, while Charisma helps you talk your way out when things go wrong. The Assassin needs significant skill in impersonation, suggestion, and manipulation – all supported by Charisma. Darkvision is also a useful racial trait for any rogue. Your abilities as a sneak thief/scout are limited if you can’t see in the dark.
We’ve selected only races that you can build into an optimal, powerhouse Assassin. But we certainly don’t dislike weird, suboptimal builds that are full of flavor with characters to match their odd stats. The suitability of certain races for certain classes follows its own consistent logic in DnD. Physically large, strong creatures get bonuses to strength and (sometimes) constitution, while smaller, faster creatures gain a bonus to Dexterity. An Assassin Rogue is probably best played by the kind of creatures you’d imagine suitable. Any large, slow, or noisy creatures will make a poor Assassin while smaller, faster, and nimble creatures fit the bill.
✅Half Elf
With a +2 to Charisma and a pair of +1 bonuses you can add to any ability score (put one in Dexterity), the half-elf makes for a pretty serious Assassin. Two free proficiencies can be used to hone your skills, and darkvision helps with exploration. This race is easy to recommend for your next Assassin build.
🆗 High Elf
The +2 Dexterity bonus is an excellent start for any Assassin. Longbow proficiency helps optimize a ranged build, and perception proficiency and darkvision are effective during exploration. The bonus to Intelligence and the Intelligence-based cantrip are less intuitive, although you could probably find a useful cantrip. Then again, your Intelligence score will likely be too low to make it effective. If you want to play as a magic rogue – go for the Arcane Trickster.
✅Wood Elf
Wood elves also get a +2 to Dexterity and perception proficiency, and their Wisdom bonus has some utility during exploration. Wisdom saving throws are useful to just about any character too. Wood elves are proficient with longbows, can hide when only lightly obscured by nature, and gain a bonus to movement speed. All in all, a pretty solid choice.
🆗 Drow Elf
These Underdark dwelling elves have perfect darkvision, from growing up deep underground. The downside to this is sunlight sensitivity, which can be a deal-breaker for many. They share the same automatic perception proficiency as all elves and most importantly, gain bonuses to Dexterity and Charisma. Magical resistance to sleep spells can be useful when scouting, as is advantage on saving throws against being charmed. Access to some drow magic is also a welcome addition, especially because it uses your Charisma score as its modifier.
✅ Lightfoot Halfling
Other than darkvision, the lightfoot halfling ticks all the boxes for an Assassin Rogue. Their +2 Dexterity and +1 Charisma bonuses are ideal for this subclass’ strengths, as is their ability to hide behind medium-sized allies on the battlefield. Their Lucky trait protects you from natural 1s – useful for any class.
🆗 Stout Halfling
The stout halfling gets the +2 Dexterity bonus and a +1 bonus to Constitution instead of Charisma. This isn’t useless, but neither is it as good as their lightfoot cousin’s stats for our purpose. Instead of a boost to stealth, the stout halfling gets resistance to poison – useful but not Assassin-specific. You can certainly build a decent Assassin with this race, but it won’t be as good as a lightfoot halfling.
✅ Variant Human
The variant human is pretty good for just about any subclass, and the Assassin is no different. A bonus feat at level one is a pretty big deal,.The +1 bonus to any two stats should be spent on Dexterity and Charisma, and the free skill proficiency of choice makes you a formidable character, even early on. The only mark against variant humans for building an Assassin is their lack of darkvision.
🆗 Tiefling
Although the +2 to Charisma and darkvision have some usefulness, a tiefling’s +1 to Intelligence won’t make for an optimal Assassin build. The thaumaturgy cantrip is also not especially Assassin-specific. Nor is the darkness spell. Resistance to fire is useful for any class and can help a rogue during exploration. But ultimately, there are better choices for your Assassin build.
🥷 Not convinced? What about playing a Scout Rogue instead?
Heroic Killer For Hire
There are rogue subclasses with more versatility than the Assassin – but none with that devastating single attack. The way we see it, Assassinate isn’t a combat-only ability. It can be used in the initial exchange of a combat scenario, but this key ability synergizes so well with the Assassin’s infiltration skills that it seems to be made for, well…assassination. If you’re in love with the cloak-and-dagger, high adventure setup followed by the kill, let us know in the comments. And if this article has piqued your interest and you go roll up your first contract killer, we’d love to hear how it goes.