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How To Play A Rogue Assassin

So you’re thinking about playing a Rogue Assassin in 5th Edition Dungeons & Dragons? It is certainly one of the most iconic archetypes in the game and one that allows you to do deadly damage to your foes, and in the right circumstances, much more damage with one blow than fighters and wizards can hope to do. Which, together with their penchant for stealth and deception, makes them a pretty exciting prospect to play.

In this post we’ll take a look at how we can build really fun Assassin characters to play (or rather Rogue characters with a view to selecting the Assassin archetype at 3rd Level), along with what skills and proficiencies are going to make you the most effective when it comes to the mechanics of the game (ie. combat and sneaking around like a mofo).

I’m a priest, honest! (Image by

Let’s look first at the roleplaying aspect, because hey, this is a roleplaying game after all, and whilst rolling dice is fun, the RPG pay off usually comes when we successfully breath life into our stats sheet…

The Character Side of Your Character


The first question that you have to ask yourself when creating an Assassin is how did they get into the killing game? Are you a cold-hearted bastard who considers that if everyone has to die at some point, why not make a profit from it? Or are you a principled killer: a vigilante who only deals death to those that have it coming to them (in your humble opinion)? Are you a religious killer… dedicated to the fatal work of your deity? Maybe you were trained since childhood by an Assassin’s Guild to be an agent of death – killing has become an instinct to you, perfected by your perverse upbringing. Consider as well that your character doesn’t have to be a 24 carat pure Assassin. Maybe they are a spy or secret agent, who just happens to be particularly good at drawing a dagger across the throats of those who stand in their way – more in the mould of a medieval James Bond.

Once you’ve answered that question you also need to consider how then you ended up with your fellow player characters, as an adventurer. Have you reformed your ways (for those starting at 1st Level this could be a bit problematic as you don’t technically become an Assassin until 3rd Level)? Are you between contracts and in need of some fast cash (if so, why… do you owe someone important a big debt?)? Has an NPC sent you to spy on your fellow players? Have you been sent adventuring by your guild to get some real world experience? Or maybe you’ve rejected and run away from your guild training (let’s hope they took it well!)?

In all cases you should consult with your DM… if you’re spying on your fellow players for example do you need to present yourself as something else and hide your Rogue abilities? Or in the example where you were raised as a child by your guild, do you at first represent the guild loyally (until at least 3rd level when you complete your training) before starting to have doubts about the life you were groomed into? This could be a great story development which you could play out. By communicating with your DM you will get ideas about how your assassin can fit into their world and their adventure, as well as how they might fit into the party, and you in turn will give them plot hooks that can shape the story you will be building together.

When I built my own Rogue Assassin I decided to create a full profile of the White Scorpions Assassin’s Guild to give more colour to my hitwoman, complete with guild history, power structure, current grandmaster, favoured killing methods, initiation ceremony and motto. I will share it soon with you!

UPDATE: I just published an e-book on the Order of the White Scorpions on DMs Guild. You can buy it for just 2.99 USD and I hope it will give you a big head start on fleshing out an awesome character.

Now available to buy on the DMs Guild…

Using Official D&D “Backgrounds”

Don’t forget to take advantage of the excellent Backgrounds section in the 5th Edition Player’s Handbook to flesh our your character (or even create them from scratch). Charlatan, Criminal and Urchin are the obvious ones to consider, but often the best character ideas come from combining two seemingly miss-matched premises. What if the bespectacled and weedy cartographer (Guild Artisan background) puts down his pen and inks at night to fire poisoned darts into his victims’ necks from his hand-made blowgun? Or maybe the boyish Orlando Bloom lookalike uses his celebrity status as playboy poet (Entertainer background) to infiltrate the palaces and castles of the rich and famous in order to do his dirty work.

Once you’ve made a decision be sure to roll on the Personality Trait, Ideal, Bond and Flaw tables. As you get a sense of your character you might prefer to choose one (or more) from each table (or from the tables of another background) than roll randomly… then again rolling randomly can do wonders for your creativity, as it forces you to join the dots in a credible way, no matter how far away they are.

Rolling randomly on the Charlatan’s tables just now I got the following:

Personality Trait
3. Flattery is my preferred trick for getting what I want.

2. Fairness. I never target people who can’t afford to lose a few coins.

6. I swindled and ruined a person who didn’t deserve it. I seek to atone for my misdeeds but might never be able to forgive myself.

2. I’m always in debt. I spend my ill gotten gains on decadent luxuries faster than I bring them in.

From these rolls I’m already getting a firm idea of a new character. A lush gambler with a love of the high life, who once – out of desperation – conned a woman who loved him out of her life fortune. She died shortly after and he has never quite forgiven himself, but nor has he managed to clean up his act completely. He still robs, cheats and cons to pay for his lifestyle, but only from the rich. He is sounding more like a Thief than an Assassin, but I’m going to toughen him up a bit by imagining he is from low nobility and an experienced dueller with the rapier. His goal in any fight is simply to win by any means necessary, preferably without exposing himself to any danger, explaining his ability to use the Rogue’s Sneak Attack ability and later Assassinate ability. In short he is a dissolute rake, with a thin sense of honour, but a sense of honour nonetheless and it could be a lot of fun playing with the ambiguities in his character.

So there you go guys… roll dem dice and watch as – out of thin air – a fully fledged character idea emerges!

(By the way, my e-book on The Order of the White Scorpions does include a new background ‘Trainee Assassin’ which would suit anyone wanting to play a character groomed for the killing game from an early age).

Important: Fitting Into The Party

Remember, whilst you might have a lot of fun spying on your fellow characters, lying to them and creating chaos, it’s not always that much fun for the others – especially if you end up stabbing them in the back with a poisoned dagger “because it’s in my character”. One of the challenges of playing Assassins, and Rogues in general, is finding a credible reason for them to be with the party and not only that but be on their side, and keep the game fun for everyone. Even if you start by spying on them, perhaps later, after they’ve saved your life more times that you can count, your loyalties and values change and you become a trusted team member.

I solved this problem by having my Assassin work for a guild who deal in strictly just killings. This meant I could play a principled character of good alignment, one who could ally easily with the objectives of my party as they performed various missions against the forces of evil.

Lovely night for a lakeside stroll isn’t it?

Building A Kick-Ass Assassin

Now that you’ve got a solid backstory, let’s engage in a bit of powergaming (I know you didn’t really come here for the roleplaying tips!) and take a look at how to build your character for maximum effectiveness.

Choosing Your Race

Dexterity is what all Rogues live and die by, so it makes sense to look at the races that start by giving you a boost on this crucial skill. That is Elf (+2), Forest Gnome (+1), Halfling (+2) and Human (+1), and potentially Half Elf (+1). The idea of a Forest Gnome or Halfling Assassin seems fairly ludicrous to me… but then again remember what I said before about mismatches leading to great characters! What about a happy go lucky, somewhat portly female halfling, a maternal figure who loves singing, cooking, cleaning… and killing people? However, if you’ve been inspired by visions of a stealthy ninja-like shadow slinking over castle parapets and firing poisoned crossbow bolts at corrupt Princes then definitely Elf, Human or Half Elf make more sense. If you consider that humans can’t see in the dark, which is a major disadvantage if you’re Assassin, I’d put Elf and Half Elf ahead. As I find the idea of an Elf Assassin incongruous with their nature (and a Dark Elf one too cliched), I’d put Half Elf as my favourite Assassin race. (Half Orcs and Tieflings as natural outsiders could be decent shouts too).

Whatever you decide bump Dex up to the maximum, as you’ll be using it for the majority of your skills, your AC, initiative and your to hit and damage modifiers. Second tier attributes are Charisma (so that you can have a lot of fun conning, charming and deceiving NPCs) and Intelligence (for Investigation, but more importantly for when you multiclass as a wizard, as I’m going to suggest!), whilst Constitution is handy if you plan to fight hand to hand in combat (more fun than pussying around with bows IMHO!), especially as you are only proficient in light armour and therefore relatively easy to hit. Strength is useless to you, especially if your DM lets you use Acrobatics for climbing checks (as our does!), and Wisdom too, as you’ll take Expertise function in Perception the only skill for which you will need it (although you will fail an annoying amount of Saving Throws because of it!).

Choosing Proficiencies

The rogue class gives you four proficiencies, you should get an extra two from your background, plus half elf as a race grants you another two, so you could start the game with a whopping 8 proficiencies – two of which you can choose Expertise in, allowing you to double your proficiency bonus. Here are the most useful ones, starting with what I consider the most essential.

Stealth – Hiding and sneaking up on foes is key to taking advantage of your Sneak Attack and Assassinate skills. Choose expertise in this.
Perception – Probably the most rolled skill check in the game, plus no one likes being surprised. Consider strongly for expertise.
Acrobatics – Depending on your DM you might roll Acrobatics for jumping over rooftops, tumbling out of windows and cartwheeling out of danger, or sometimes Athletics. I love Acrobatics but possibly if you have a high Dex. anyway and your DM insists on Athletics checks for climbing and jumping choose Athletics instead.
Athletics – See above.
Sleight of Hand – Useful for slipping poison into your victim’s wine and other subtleties.
Deception – Fast talking, lying, charming or disguising yourself.
Insight – For determining if others are lying to you.
Investigation – Useful for finding traps and hidden objects, although many DMs use Perception checks.
Persuasion – For general charm.
Arcana – Useful if you want to multiclass as a Wizard later.

Optimising Combat

One weapon combination really stands out for Assassin’s as the best and that is fighting with two short swords (or for a more oriental flavour scimitars), one in each hand. The rules state (p.195 of the Player’s Handbook) that as long as both weapons are “light” then you can use your main action to attack with one, and your bonus action to attack with the other. As shortswords (and scimitars) are not only “light” but also “finesse” weapons you can use your Dexterity modifier for both attack and damage rolls (note, when you use your bonus action to attack with your offhand you don’t get a damage bonus however). This means you can not only use your best skill modifier in combat but you get more attacks than most fighters at first level. There’s an additional reason for favouring two weapons however. As a Rogue you will want to be initiating combat more often than not, jumping out of shadows to get your Sneak Attack / Assassinate bonuses. Once you’ve been spotted however getting your Sneak Attack bonus is harder… you may have to dissolve into the melee to reappear somewhere else, or flank a creature already engaged in the fight… which means you really don’t want to miss your initial thrust, or any other time you get a Sneak Attack. With two chances to hit that means even if you mess up your first attack, you can still strike using your bonus action and ensure your Sneak Attack damage gets dealt (you can only do Sneak Attack damage once a turn).

Aside from two shortswords / scimitars (or daggers if you fancy a weapon you can throw as well!), you will want to carry a range weapon. Range weapons still qualify for Sneak Attack and since you’re likely not to the toughest or heavily armoured dude on the battlefield being able to keep your distance on occasion is invaluable. Unless you’re a shortass (halfling or gnome) then a longbow beats a shortbow, and whilst a crossbow is stylish if I was the DM I would find ways to penalise anyone trying to sneak around with an 18lb heavy crossbow, so a light or handcrossbow makes more sense.

Finally, whilst you might put yourself at a disadvantage in terms of game mechanics, an iconic weapon can lend a lot of fun flavour to your character. For this reason you might want to consider fighting with a scimitar and sickle, blowgun, or perhaps poison-coated whip. Check out this list for inspiration. Seriously regretting not arming my own character with a Xena Warrior Princess style Chakram. Speak to your DM about making fair rules for any new weapons.

Using Poison

Poison somewhat problematic in D&D as really there’s little reason why an Assassin wouldn’t be using deadly poison nonstop… other than the fact it would unbalance the game. I guess for that reason using poisons is expensive and a little impractical. In the Player’s Handbook (p.153) it lists a vial of basic poison as 100 GBP and says that is only enough to coat one blade, or three pieces of ammunition. So not much bang for your buck. Worst of all it does a measly 1d4 damage – and that’s only if the victim doesn’t succeed a DC10 constitution check. Considering that it takes an action to apply the poison in the first place, this is underwhelming to say the least. After level one it’s completely pointless.

The Dungeon Master’s Guide attempts to come to the rescue (p.257 and 258) with a more detailed list of potentially deadly toxins, although all of them are fantasy poisons that retail at outrageous prices (I would have preferred some poisons from the real world at sensible prices). The most attainable is Serpent Venom, harvested from giant poisonous snakes and retailing at 200 gp a dose, which does a semi-respectable 3d6 damage – although again the saving throw DC is just 11. You’ll need to pay ten times the amount (ie a whopping 2000 gp!) to get a dose of venom worthy of the name in the form of Purple Worm Poison which does 12d6 damage, with a saving throw DC of 19.

The ingested poisons, for slipping into someone’s cider glass, are priced similarly, and make you wonder why you couldn’t just administer some hemlock or rat poison for a fraction of the price that might in addition do the job it is intended to do. Something like Assassin’s Blood, 150 gp, does a paltry 1d12 damage and is saved on a DC10 anyway. Hardly your toxin of choice for a high profile hit job. (It is at least one of the few poisons that gives the victim the actual condition of being “poisoned”. According to p292 of the PH: a poisoned creature has disadvantage on attack rolls and ability checks).

Finally the rules for harvesting poisons are perhaps the most ridiculous… you can read them yourselves (DMG p.258) but in most cases you are more likely to do damage to yourself than harvest a lethal dose.

Overall you are probably best speaking to your DM about what poisons you have access to, and what are the rules that govern using them. Laying low creatures with every nick of your blade is obviously going to make your character massively overpowered, but at least semi-frequent use of toxic materials should be part and parcel of playing an Assassin IMHO. (Remember as well that poison won’t work on many creatures like undead, demons and supernatural beings, whilst as a DM I would always give large creatures advantage on poison saving throws as obviously it’s exponentially harder to bring down an Ogre than a kobold with a nasty dose).

If there’s any shout for it, I might even create some new poisons for 5e D&D. Let me know if that you would interest you in the comments!

UPDATE: I do include playtested rules for a new poison in my aforementioned e-book. Deathstalker Scorpion Venom is an injury poison, a concentrated dose of which brings on temporary paralysis (on a failed save) allowing its administrator to dispatch their victim.

Your Equipment

As a Rogue you start with Leather armour, which is a bit of a joke as it only gives you AC 11 instead of 10 with no protection whatsoever. Real life leather armour is actually really tough, so not sure why WOTC nerfed it for 5th edition. Anyway it only costs 45 gp to upgrade to studded leather, giving you AC 12, which is sadly as about as high as you’re going to get for armour alone – luckily your dex. modifier as discussed is your best friend and you should have minimum 16 dex. (+3 modifier) to start with, which you’ll be able to take to 18 (+4) when you reach level four.

Armour aside you also get a Burglar’s Pack (p.151 of PH), which contains, I quote: a backpack, a bag of 1000 ball bearings, 10 feet of string, a bell, 5 candles, a crowbar, a hammer, 10 pitons, a hooded lantern, 2 flasks of oil, 5 days rations, a tinderbox and a waterskin. The pack also has 50 feet of hempen rope strapped to the side of it. Plus Thieves’ Tools (p154 of PH), which contains, I paraphrase: a small file, a set of lock picks, a small mirror mounted on a metal handle, a set of narrow-bladed scissors, and a pair of pliers.

The ballbearings can be useful to aid an escape… see also caltrops (both p.151 of the PH). I would definitely add a grappling hook to your list of possessions and maybe a wrist sheath, from which you can surreptitiously pop a knife/dagger in case of emergency. If you can dig out the old 2nd edition Thieves Handbook it had a load of good ideas to supplement your equipment with the likes of marked cards, loaded dice, blinding powder, weaponblack and more. Discuss with your DM what they might allow.

Don’t Miss This Feat!

Generally speaking when you have the chance to go for an ability score improvement or a feat, you’re going to want to take the chance to add another +2 to your Dexterity. As this will increase you modifier by +1, and that modifier goes on your AC, your attack rolls, your initiative and many skills checks… however there is one feat that is well worth selecting in my experience. And that is Alert. It doesn’t sound too sexy at first, its main boon being a +5 to initiative but when combined with your high dex. it pretty much guarantees you will always act first in combat, often allowing you to kill a foe before they have time to strike. Indeed, let’s read again the wording of the Assassinate skill which says: you are 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 other words you can use Sneak Attack even without sneaking if you act first. (Of course it’s much better if they are surprised because: any hit you score against a creature that is surprised is a critical hit . Remember, in the case of surprise you would be getting your Sneak Attack anyway, but with Assassinate it becomes a critical Sneak Attack, meaning you roll ALL your damage dice twice, then add any modifiers).

I can’t really emphasise how much acting first is an advantage for a rogue so select this feat and find out for yourself. The only other tempting feats for the Assassin are Sharpshooter and Lucky, the latter of which is banned on our table as it’s like having three inspiration points a day. Which is plain silly.

I would recommend taking the +2 to dexterity at 4th level and picking up the Alert feat at 8th level.


What’s more deadly than an Assassin? An Assassin that can radically alter their own appearance, create an illusionary diversion, make guards magically fall asleep or even turn themselves invisible. Whilst most Wizards don’t want to use their precious spells slots on utility spells, preferring to stake their authority in combat with the likes of thunderwave and fireball, there are dozens of 1st and 2nd level spells that perfectly compliment your roguish abilities, making multiclassing as a wizard a fantastic option for optimising your gameplay.

Using the prestidigitation cantrip you could snuff out a candle, before closing in for the kill in a darkened room. Or on the battlefield you could use misty step to appear behind your opponent, granting you advantage (at the DM’s discretion), and therefore Sneak Attack bonuses on your strike. Need to beat a hasty retreat from the palace? Grease, fog cloud or web will all slow down those pesky guards… or select my personal fave way of exiting the building by jumping out of a top floor window and casting feather fall as a reaction on the way down. Also worth noting, the easily neglected shield spell is a life saver, literally, for combat situations and can also be cast using just a reaction.

More Inspiration

Hopefully this article has got you excited about playing a 5th Edition Rogue Assassin. Don’t cop out of roleplaying by opting for the “silent killer” mould though… use my tips to come up with hitman with both personality and power. If I haven’t got your creative juices flowing yet then why not take some inspiration from some of fiction’s best loved assassins, like Nikita, Leon, Altaïr ibn-La’Ahad, 007, and many more. NerdMuch have a list of eight of the best, whilst you can find a pretty comprehensive list on Wikipedia.

A reminder that you can find the stats and personality of my own dagger in the dark, Xenia “Night Sting” Zanetti together with a profile of the guild she works for: The White Scorpions on this very blog.

You can even power up your PC, give them a tonne of extra credibility and support the handsome, kitten-saving, environmentally sustainable and downright loveable – but very poor – guy behind Hipsters & Dragons by buying his e-book.

>>> Buy The White Scorpions Assassins Guild for 5th Edition Dungeons & Dragons <<<


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  1. Don Arnold

    any way to one shot a target, or do i just need more research
    great ideas and i am getting the e-book

    • duncan

      Hi Don, not quite sure what you mean! Do you mean take down a target in one shot? Well obviously the assassinate ability you get at 3rd level helps a lot. If you are able to surprise a target then you would get a sneak attack auto critical hit. On a critical hit you roll all dice twice, so even at third level you’d get your weapon (shortsword let’s say) 1d6, plus 2d6 sneak attack, so total 3d6, which would make 6d6 critical with assassinate ability. Plus whatever poison you were using. Should take down a pretty decent sized opponent! Plus with alert feat you’d almost certainly win initiative and act first in next round if you didn’t get the job done in round 1. That way you’d get to use assassinate again (as it works before your opponent has taken a turn in the combat, have a read in the Player’s Handbook)… you wouldn’t get critical this time, as your opponent would no longer be surprised, but you’d get advantage meaning you can deal your sneak attack damage again. So in this example another 3d6.

    • duncan

      ps. thanks for offering to get the e-book! I think it will make playing an assassin more fun. The poison I homebrewed is perhaps a little powerful, so if you are kicking too much ass you could maybe reduce the saving throw by 1 or 2 points. If you are able to review in on the DMs Guilds that would be much appreciated too!

  2. Tony

    I’ve had a lot of fun playing an Assassin/Fighter (Battle Master) multiclass. He’s currently 16th level (Fighter 9/Rogue 7). The battle maneuvers and superiority dice are great, especially if I get the much coveted assassinate in round 1 so I can do an additional 2d8 damage, but also in later rounds (making the post 1st round assassin much better, IMO). Extra attack is nice, too. He’s a ranged fighter, using a longbow primarily. It’s pretty fun to use trip attack with an arrow while the bad guy is surrounded by the party tanks, giving them advantage on their next attacks (as long as they go before the baddy).

    As for his reason for becoming an assassin, his parents were killed by henchmen of an evil overlord when they refused to pay more than their normal “protection fee”. He made his way to the nearest city, where he found work as a stable boy for an aristocrat with an adventuring past. His new lord trained him in the art of assassination, and in exchange for room and board he would do various “tasks” using his new skills. His goal is to find and kill the overlord and anybody who works for him.

    • duncan

      Hi Tony he sounds pretty badass, and that’s a solid backstory. I love the Battlemaster Maneuvers too, and they work very well when you multiclass. Has your DM utilised your backstory in their campaign?

  3. Jason

    Thanks for this.

    I too was thinking of a Rogue-Assassin with Wizard crosstraining although my thought was to start with a pure Elf (gotta love the immortal/long lived races).

    Though he is an elf he grew up around human children and absorbed a lot of their bad habits, including being somewhat light fingered. His main shtick is that he doesn’t really like killing people (but he’s an assassin, go figure) so he generally prefers to trap and immobilize his enemies (work it out with the DM so targets he takes out are usually “captured” not “dead”).

    With his sky high charisma there are even times where he robs someone, and then they go and have a drink and laugh about it afterwards.

    • duncan

      Hi Jason

      Sounds like a fun character, but perhaps more of an arcane trickster? The assassin’s skills are going to be wasted on someone who doesn’t stick the knife in, whilst the arcane trickster allows you to keep levelling up as a rogue whilst gaining arcane powers that could help you cause mischief… (your PC concept seems more like a mischief maker, than cold blooded killer).

      On the other hand, if you stick with assassin, maybe try to answer the question where he got his deadly skills from. Was he trained, but rejected his training? Or did he grow up in a real rough area of town, where life was cheap, and he had to learn how to defend himself. Perhaps you could ask your DM for some kind of paralysis or sleep poison that enables you to capture victims alive… although be aware, it can be a drag having a bunch of prisoners on an adventure mission!

      Let me know how it goes on when you start your campaign!

      • Jason

        I thought a bit more about it and you’re right. He does seem more like the mischief making Arcane Trickster than the serious Assassin type.

        It’s not like the Rogue class is short on damage potential. Being a High Elf Rogue would make him a very well rounded character, and between Elf and Rogue proficient with a variety of weapons, although running into the jack-of-all-trades-master-of-none problem.

        There is the Winged Tiefling Rogue idea, but that’s probably a bit silly.

        Actually, a Winged Tiefling Rogue Assassin could be interesting. Dropping on silent wings onto a victim, lifting them into the air and dropping them. Of course “Winged” replaces their stat bonuses, but still… And whenever you’re asked, “Who are you?” you can reply, “I’m Batman.”

        • Jason

          Sorry, misread that. “Winged” replaces “Infernal Legacy”.

          The Feral Winged Tiefling still gets +2 Dex and +1 Int, and 30 feet flying speed.

          Not bad.

          • duncan

            Yeah, that’s a massive advantage!

            As a DM I don’t allow winged PCs because it makes a lot of fun and challenging situations redundant…

            “You come across a daunting cliff 100 feet high”… “I fly up and drop a rope down”

            “The bridge is destroyed, leaving no way to cross.”… “I fly over with a rope and create a zip line.”

            “The assassin shimmies up the wall like a gecko.”… “I fly up and stab him in the back”

            I don’t even like the spell Fly to be honest for the same reason! I am thinking about making it a 4th or 5th level spell for my next campaign.

            So you might want to do your DM a massive favour and stick to the Arcane Trickster!

            Ps. the Cloak of the Bat (in the DMG) is a good way to imitate Batman if you can get your hands on it! Is a fun way to fly, with limitations that stop it breaking the game (must be dark and you have to hold the edges of the cloak).

  4. Akenma

    Going elf so that you can pick up the elven accuracy feat makes assasin an amazing class as elven accuracy gives you three rolls for advantage instead of two.

    • duncan

      Hey Akenma, good tip. Haven’t checked out the racial feats yet properly, so must do that soon, and see what else is there!

  5. Roger

    One thing I would like to warn potential Assassins about is the nature of surprise in 5E D&D. Per the PHB and errata/sage advice,

    1) Surprise is not a round, it can occur during the first round of combat, but that is dependent upon a lot of factors, many of which are not under the players control. Remember, 5E has no facing, so if you move out in the open to backstab, you reveal yourself and lose stealth (although you may still gain surprise).

    2) Even if you get surprise, you have to beat your target in initiave to get the autocrit. This is a huge issue, and pretty much makes Alert mandatory. Even if you have alert, a 16 dex, and surprise, you will lose initiative about 35% of the time. This means both advantage and autocrit are not available.

    3) If you are playing at a table with a large number of folks, you will almost never get the chance to sneak up on folks. That is not a rule issue, just an artifact of being in a large group, some of which will likely be loud or not sneaky. Smaller groups are easier, but even then it is not an ability you wil use in every combat (unlike insightful fighting or Skirmisher or fancy footwork.)

    All of these things together make assassinate really weak RAW. Of course your table might use different rules regarding surprise and stealth which would rap up the value of that ability quite a bit. But if your goal is to be the guy who opens up the combat with a quick kill of the baddies, there are far better options.

    All of that having been said, assassin can still be a blast to play.

    My rogue is currently 7. Once I realized the weakness of assassinate, I decided to go a different route. I am planning on going to 8 in rogue, taking Prodigy, then going 4 levels of Bard (lore) and then going back to Rogue up to 20. The build will be going full skill monkey. 4 levels of Lore Bard will give give me another 2 expertise skills and Jack of all trades , and an ASI for Actor. Prodigy will give me yet another expertise and yet another proficiency. When I get to 10 rogue (admittedly a ways off) I will get reliable talent. At character level 12 (8/4) I’ll have expertise in 6 skills and proficiency in 5 others. The remaining skills will get JoAT. With a minimum skill roll of 10.

    combine that with the additional abilities Assassin’s get in infiltration and Imposter and the actor feat, and you have the perfect spymaster. And dont forget the Bard spells (Disguise self, invis, Enhance ability, and even Speak with animals). Someone who can gather intel, create networks of contacts, eyes and ears, and interrogation. Being the party face is also a role you fit well. I am also creating alternate personas that you can use for different purposes. (it is a city campaign so far)

    Sure my combat ability(sneak dice, ASIs, etc) will drop off due to this, but it will still be a ton of fun.

    From a backstory standpoint, my character started out as part of a hit squad, his squard was betrayed and killed, and he went on the run. He met up with a merc group and has been running with them. After some RP stuff occurred, he realized that martial prowess, the thing that had defined him his entire life, was failing him and that the real power came from information.

    Im in the process of RPing the change, starting my personas, establishing informaiton networks, etc. (all during downtime so it does not interfere with other players). Then I can introduce/use this stuff during play sessions and really confuse and entertain the group by showing up as another person, playing the drums badly, having contacts to help us gather info, etc.

    It has been great fun. I expect the campaign to last long enough for me to see this through.

    • duncan

      Hi Roger

      Thanks for the detailed comment, and ideas for a ‘spymaster’ build!

      Regarding, assassinate, my experience was that it was an incredibly powerful ability. My party would always let me take the lead in any combat encounter where we spotted the enemy, and with expertise in stealth I rarely gave myself away, allowing me to get a critical hit in the first round of combat pretty reliably, which with sneak attack damage was always particularly deadly. I was doing some insane damage at times. Remember you can also use assassinate with a ranged weapon, making it even easier. If you have a party that charges in and doesn’t let you scout ahead then yes, the ability is seriously compromised.

      With Alert feat and dex of 18, I hardly remember losing an initiative contest. On the other hand, if one opponent beats you in initiative you could always attack a second one that doesn’t.

      In a dream scenario you take out the big bad in the first round with your automatic critical hit (during which the enemy party is surprised), and then win initiative in the second round and get advantage and sneak attack damage on the second biggest bad, before they can act. After that you’re ready to let the rest of your party mop up.



  6. Steve

    Nice advice and definitely tips I’m using to make up my Half Elf Assassin as my backup character. Thinking of taking 3 levels of Bard later on to really make a highly skilled character and just thought I’d ask to see if it would be good to do. Roleplay wise, she’s very…sociable for a hired killer, and I like the idea of playing a friendly, cheerful and amiable adventurer who just so happens to be a criminal in the cutthroat trade. Any tips or advice would be greatly appreciated. Thanks!

    • duncan

      Hi Steve

      Sounds like a fun character concept… mechanics-wise and I’d probably take 5 levels of Rogue to get 3d6 sneak attack damage and uncanny dodge and then segue into Bard. Partly because at 6th level Rogue you don’t pick up anything too fancy, apart from a second hit of expertise and you’ll going to get that at 3rd level Bard anyway.

      Take a look at the Bardic Colleges in Xanathar’s Guide… the College of Whispers looks like a perfect fit for an assassin multi-class!



  7. Ashley

    So, new to D&D and we’re just in the beginnings of Strixhaven. I am the ludicrously mentioned forest gnome that happens to be a rogue charlatan assassin teenager from a kingdom of forest gnomes. Mum and the other women are the trained assassins in this realm. My father, the king, is less on killing and has a good heart, but is in the position he’s in and the responsibilities and whatnot. We are about to pick our schools. I’m stuck between Witherbloom and Silverquill. I’m more like my dad and don’t want to kill. I rather incapacitate, sneak around, spy. Basic background is I’m sent to school to spy for my father, but also to get away from mum and her push towards a life I might not want. Thoughts? I like the idea of potions/poisons, but also using words to persuade. Definitely like the sneaking, lurking, changing appearance that a rouge might do.

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