If you like to get Critical Hits on your big Sneak Attacks but don’t like the idea of Crit Fishing, perhaps the Assassin is the Rogue for you. You’ve probably already looked at the Assassinate feature and want to capitalize on those guaranteed Critical Hits, but guaranteed is not the same as free. You’ll have to work with your party to Surprise your foes in order to earn those Critical Hits.

Surprised is a simple condition that is much harder to achieve than you might think. If your whole party’s Stealth checks beat the Passive Perception of a foe, that foe is Surprised. Yes, even that Paladin waddling around in plate armor. If a foe detects even one of your allies, that foe is not Surprised. That’s the official definition for how Surprise works in Dungeons and Dragons 5e. We went into extreme detail on this in the Stealth episode which also proposes some fixes if you want too.

Things get murky when we consider why the Assassin also has a pair of features designed around Deception and Infiltration. The rules of Surprise only mention Stealth and Perception, but we could (and do) argue that Deception versus Insight should also be a valid method of imposing Surprised on a target. That stompy Paladin from earlier certainly has enough Charisma to lie through their teeth.

Table of Contents


RPGBOT uses the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.

  • Red: Bad, useless options, or options which are extremely situational. Nearly never useful.
  • Orange: OK options, or useful options that only apply in rare circumstances. Useful sometimes.
  • Green: Good options. Useful often.
  • Blue: Fantastic options, often essential to the function of your character. Useful very frequently.

We will not include 3rd-party content, including content from DMs Guild, in handbooks for official content because we can’t assume that your game will allow 3rd-party content or homebrew. We also won’t cover Unearthed Arcana content because it’s not finalized, and we can’t guarantee that it will be available to you in your games.

The advice offered below is based on the current State of the Character Optimization Meta as of when the article was last updated. Keep in mind that the state of the meta periodically changes as new source materials are released, and the article will be updated accordingly as time allows.

Assassin Features

  1. Bonus Proficiencies: Both tool kits are fantastic and open up wonderful options for the Rogue.
  2. Assassinate: To make this work, you really want to go first in combat for that free Advantage. Maximize your Dexterity as soon as possible, and consider the Alert feat. If magic items are available to you, try to get a Weapon of Warning.

    Free Advantage is well and good, but what about those automatic Critical hits? For those we’ll need to work harder. Surprised can be thought of as a Condition and it’s not easy to impose on a foe. By the rules, to Surprise a target your whole side has to succeed at Stealth checks versus a foe’s Passive Perception. Each foe may or may not be Surprised on an individual basis, but essentially your whole party has to win at Stealth.

    This might sound tough, but the Surprised condition is rather debilitating even without this feature, and will benefit your whole party immensely. I don’t suggest you try to force your party into a Stealth setup, but rather see if they want the tactical advantages and are willing to try it out. Anyone that can cast Pass Without Trace will do wonders to amplify such a party, of course, but even simply having everyone get Stealth proficiency is helpful.

  3. Infiltration Expertise: Rules as Written, Surprised is Stealth versus Perception, but Surprised is also up to the DM. If you’re playing an Assassin (or if you have an Assassin player in your game), I would suggest that Deception versus Insight is equally valid for imposing Surprise. You’re not a band of murder hobos, you’re a humble merchant and this is your staff. And then you Surprise them with murder.

    Obviously this is only useful if your campaign has situations where lying like this will be helpful. Many campaigns just don’t have situations where you can be an operative on the inside.

  4. Impostor: Infiltration Expertise is for making up a whole new person, but this is for taking over as an existing person. It should be useful about as often as Infiltration Expertise, which is to say that it very heavily depends on the campaign.
  5. Death Strike: If Surprised is so hard to pull off, why is this rated so highly? Well, if you’re playing such a high level Assassin, I would assume your whole party has bought into the Surprise attack way of doing things. With even a small amount of magical support, Surprise is far easier to achieve.

Assassin Ability Scores

The Assassin’s primary scores will follow the scores in the Rogue Handbook, but our features do steer us towards Face skills as a secondary concern.

Str: It’s always technically an option to use Strength as a Rogue, but typically impractical. For Assassins attempting to Stealth for Surprise, this is doubly true.

Dex: AC in Light Armor and Attacks with Finesse or Ranged weapons. Important for us.

Con: Keeps us alive and these saves are really bad to fail.

Int: Technically we can use this with our Poisoner’s Kit proficiency but that’s about all we can get out of it.

Wis: It’s about as useful to us as it is to most people, i.e. Insight, Perception and Saves, but we don’t get anything special out of it beyond that general utility.

Cha: We gain some benefits to Deception and Disguise that would benefit from Charisma. If your DM agrees with my assertion above about Deception vs Insight for Surprise this might even jump to Blue.

Point BuyStandard Array

Assassin Races

There are some interesting ideas to consider here, but also browse the Rogue Races Breakdown for other options.

  • Bugbear: The synergy of the Surprise Attack feature just compounds hard if we can get Surprise because of the bonus 2d6 damage being multiplied on our automatic critical hits. Long-Limbed is also pretty nice.
  • Earth Genasi: Pass Without Trace is really helpful, not only for someone already good at Stealth but for everyone else who isn’t quite so proficient. As someone without Spell Slots, it becomes a bit difficult to use more than once per day but we have two solutions. An ally spellcaster could use this race to add the spell to any caster or we could dip a few levels into a spellcaster ourselves. Three levels into Warlock would honestly do the trick.
  • Harengon: All of our setup and work on being Stealthy enough to get Surprise means absolutely nothing if we don’t also win initiative. Adding our PB to those checks is a massive advantage on its own, but read Reliable Talent carefully: An ability check where we can add our PB. Harengon Rogues have a floor of 10+Initiative Modifiers after level 11.

Assassin Feats

The most important feat is already called out as blue in the Rogue Handbook.

  • Alert: All of the key parts of Assassinate require us to go before our foes in combat, so adding another +5 to our Initiative swings the odds even further into our favor.

Assassin Weapons

The safer option is to use a ranged weapon, both for staying out of enemy reach and because we have a single turn to take advantage of Assassinate. We can’t risk being too far away to stab a foe before losing our bonus.

Assassin Armor

Just wear Studded Leather.

Assassin Multiclassing

There are plenty of theoretical builds where someone takes three levels of Assassin Rogue so they can drop Phat Crits by surprising targets with tons of dice. But for an Assassin, look for options that improve our Initiative or our party’s Stealth.

  • Twilight Cleric: A few levels will get you Advantage on Initiative forever and a couple spell slots in case you do decide to pick up Pass Without Trace racially.
  • Fighter: A couple levels for Battle Master (or a single level for Fighting Style (Superior Technique)) gets you access to the Ambush maneuver, and if you take it to 5 you get to double your chances of landing an attack in a turn to apply sneak attack (in case you haven’t convinced your party that stealth is good enough to reliably Death Attack).

Assassin Party Support

The Surprise mechanic RAW is all or nothing based on your party’s ability to roll Stealth. The result of this is that a blindly assembled party without any regard for being sneaky is no better at getting the Assassin those surprise crits than someone just trying to go crit fishing any other way. But we love math, so I asked our Patreon Discord to blindly give me a Cleric, Fighter, and Wizard to team with our Rogue here.

I was given Twilight, Rune Knight, and Divination. We’ll be using the example builds from those handbooks to determine how likely we can get surprise against the Passive Perception of a monster with Perception Proficiency and 12 Wisdom.

Level 4 DC 13: We’re going to start the calculations at this level as each PC has received their first ASI and the Assassin has Assassinate.

Assassin: With 16 Dexterity and Expertise in Stealth, the Assassin has a +7 to Stealth at this point. That gives us a 6 on the die, or a 75% chance to pass.

Twilight: With 8 Dexterity, no Stealth Proficiency, and Heavy Armor, we need to roll a 14 with Disadvantage. 12.25% chance.

Rune Knight: It’s only a little better than the Twilight build, having a 12 in Dexterity but otherwise also no Stealth and in Heavy Armor. A target of 12 with Disadvantage for 20.25%.

Divination: We’ve got 14 Dexterity, no Proficiency, but also no Disadvantage. Without spending any resources we need an 11, 50% chance.

The chances that everyone succeeds at this check and we gain surprise is 0.93%. And without any investment it just gets worse from here. But we could spend some resources to mitigate some of the problems. The Wizard and Cleric both have access to the spells Borrowed Knowledge and Enhance Ability and the Divination Wizard has Portent Dice.

Let’s look at level 8 DC 14 and assume everyone wants to help with the resources they can spare.

Assassin: We’re at 18 Dexterity now so we’ve gotten a bit better with a +10. That’s 4 on the die, 85% chance.

Twilight: Spending two spell slots for Borrowed Knowledge and Enhance Ability to get Proficiency and Cancel the Disadvantage, we need a 12 on the die, a 45% chance.

Rune Knight: The Wizard is casting their Enhance Ability as well, to cancel our Fighter’s Disadvantage but alas they have no easy way to gain proficiency. They need a 13, 40% chance.

Divination: With Borrowed Knowledge running, this Wizard only needs an 8, 65% chance.

That’s technically better: we have a 9.945% chance to surprise the target. That’s a whole 0.195% better odds to critically hit than just rolling with Advantage. By spending 4 level 2 spell slots. Why are we doing this again?

It’s not going to get better, and this illustrates the importance of building characters as a party. So let’s hand pick our allies. First, the Trickery Cleric, who could almost compensate for anything else by virtue of Pass Without Trace (as could any Druid or Ranger). Beast Barbarian because in round two onwards we need somebody next to the targets for Sneak Attacks. And Genie Warlock because Sanctuary Vessel is another way to cheese some Stealth and Surprise. We’ll re-run the calculation here at level 8. Still DC 14.

Assassin: This time, with our party fully on board and committed to Surprise tactics, the Trickery Cleric is running Pass Without Trace so our bonus is now +20. We literally can’t fail this DC.

Trickery: Stealth proficiency, PWT, and 16 Dexterity. That totals +16. Also impossible to fail.

Beast: No proficiency, 14 Dexterity, PWT, +12. We pass on a 2 and roll with advantage thanks to the Trickery Cleric’s Blessing of the Trickster feature. 99.75% chance.

Genie: Stealth Proficiency, 18 Dexterity, PWT. +17 for another automatic success.

So Pass Without Trace is incredibly broken and you should just use it all the time if possible. You don’t even need an Assassin on the team, that’s just a bonus. Surprise is a free round of turns. If everyone has Stealth Proficiency, which is easy to gain through background choices, it’s far better and works on more perceptive foes, but even without it our Beast Barbarian does just fine. 

And just to show that off, PWT with our loud and stompy friends from earlier:

Twilight: Now needs only a 2, with Disadvantage that’s a 90.25% chance.

Rune Knight: Needs a 3, so 81% chance.

Divination: Automatically succeeds against our DC.

Example Assassin Build – The Killer Rabbit of Caerbannog

What? Behind the rabbit?

It is the rabbit.

Monty Python and the Holy Grail

The key feature of the Assassin is Assassinate. In order to use it, we need to win initiative when going into combat. Harengon will help us accomplish this thanks to adding PB to those rolls as well as the likely unintended interaction between Reliable Talent and Hare-Trigger.

Our initiative modifier starts as +5 at first level before jumping to +10 as we acquire Alert at 4th level. It then climbs with each Dexterity ASI and PB increase, reaching +14 by tenth level. At eleventh level something special happens: previously our lowest possible initiative was a 15 by rolling a natural 1, but once we have Reliable Talent our floor becomes 24. At this point, many monsters simply cannot beat our initiative check, so we will always have Advantage on the first round to open with a sneak attack without having to wait for an ally to get into position.

You will notice I haven’t mentioned Surprise at all yet. Reliably surprising your foes requires the whole party’s involvement and commitment to getting the drop. If your party wants to do this occasionally, that’s great. We’ll mostly assume getting Surprise is a bonus some of the time and focus on the free Advantage we can control.


We start with point buy and put 15s in Dexterity, Constitution, and Charisma. Then we choose to add +1s to each of those for 16s in everything we care about. Truth be told, you could just ignore the face skills if you wanted to have a different set such as picking Wisdom for Perception and Insight boosts. We’re not doing that here, but it’s an option. Just because you have features for disguising and deceiving doesn’t mean you have to use them if they don’t fit your campaign.

BaseIncreasedLevel 20


We’re picking Harengon as mentioned above. Primarily so we can almost guarantee going first in fights. Getting Perception and Rabbit Hop are just bonuses on top of Hare-Trigger. Rabbit Hop might seem redundant with Cunning Action, except it’s like combining Dash and Disengage. When you only need one of those, use Cunning Action, but if you really need to do both in one turn, spend a Rabbit Hop.


We take the Faceless background for Deception and Intimidation. Because we’ll be getting Disguise Kit proficiency from Assassin, we can trade it out for something else. My example build picked Flute just because I can, but you do you.

Skills and Tools

From Harengon, we gain Perception. From Rogue, we gain Acrobatics, Insight, Persuasion, and Stealth. From Faceless we gain Deception and Intimidation.

Because we get to choose Expertises as a Rogue, we choose Deception and Stealth at first level and Insight and Perception at sixth level.

For Tools, we gain Disguise Kit and Poisoner’s Kit from Assassin as well as the standard Theives’ Tools that all Rogues get.


At 4th level, we choose Alert for +5 to Initiative as well as other useful benefits.

At 8th level, we gain an ASI for +2 Dexterity, bringing us up to 18.

At 10th level, we take a second ASI for another +2 Dexterity, maxing out at 20.

At 12th level, we take Inspiring Leader because we have the Charisma to qualify for it and it’s just that useful.

At 16th level, we’re taking Resilient (Constitution). Yes it’s an odd choice, but Rogues gain Wisdom Proficiency at 15th level and just for fun and to lean into being the killer rabbit that nobody can seem to scratch in that scene, why not be proficient in the big three saves?

At 19th level, you might pick Skill Expert so that you can add +1 to Constitution and round that number to 18 while getting a skill and an expertise. You might also pick up Aberrant Dragonmark for the same Con boost, but with weird spellcasting based on Constitution. I’m choosing Durable because we’re already encouraging the team to take more Short Rests with Inspiring Leader and that gets us a floor on our Hit Die rolls. It also plays into the killer rabbit bit more so it doesn’t matter that it’s objectively bad when I’ve already told you the better options.


LevelsSneak AttackFeats and FeaturesNotes and Tactics
11d6Sneak Attack

Thieves’ Cant

Skills (+ Expertise)

-Thieves’ Tools
We start like most Rogues. A shortbow or a hand crossbow and some light armor is our equipment of choice.

Sticking to range and bouncing Sneak Attacks off of preoccupied opponents engaged in melee with our allies keeps us from getting hit.

Our skill selection plays into the Face role. While I can’t assume your DM will agree that Deception could impose surprise in some situations, I can still build in that direction.
21d6Cunning ActionBonus Action Dash, Disengage, or Hide. Good options for using that. We can use this when we only need distance or short combat mobility and save our few uses of Rabbit Hop for when we need a mixture of both on the same turn.


-Disguise Kit
-Poisoner’s Kit
Now we get to start our speedy sneak attacks. From now on, we have Advantage against anyone we beat in initiative during the first turn. As a primarily ranged Rogue, going first can actually be rough since none of our allies are in position to help us get Sneak Attack, so this is just a free Sneak Attack on round one.

Surprise is tough to gain, but if we do pull it off, we gain automatic critical hits because we already gain the Advantage we would otherwise gain from Surprise. So just remember that Surprise Crits are just a bonus if we put in extra work and not the primary way to play an Assassin.

For a little DPR math we’ll compare our first round Assassinate sneak attacks with a Shortbow as an Assassin with and without Surprise. This means both attacks have Advantage. For comparison, target DPR for this level is 9.6 and high is 19.2.

Normal: 12.87
Surprise: 21.06
42d6Feat: AlertWith Alert, we add +5 to our Initiative and also become immune to surprise.

Breaking down our numbers, we have a 16 Dexterity for a +3, Hare-Trigger is adding our +2 PB, and now we have another +5 from Alert.

In total that gives us +10 to our Initiative checks so we should be winning most initiatives for our one free sneak attack.

This does put us behind the Fundamental Math, but it makes us more likely to use our signature feature, so it’s worth the trade.
53d6Uncanny DodgeTake Less Damage.
Our Wisdom isn’t the greatest, so these Expertises help compensate for that. Alternatively, we could do Intimidation and Persuasion for oppressive Face rolls.
74d6EvasionTake No Damage.
84d6ASI: Dexterity +2 (16=>18)Attacks, AC, and Initiative.

This brings our initiative bonus to +12. We’ll be increasing again shortly, hitting +14 by level 10.
95d6Infiltration ExpertiseSpend time and money to stop people from even getting to roll against your Disguise until it’s too late.

I would be surprised if you couldn’t impose surprise with this in the relevant situations.
105d6ASI: Dexterity +2 (18=>20)Capped Dexterity, and just in time for the fun next level.
Since we’ve capped our Dexterity, let’s check back in on those DPR calculations.

Same details as explained at level 3.
Target is 18.3, high is 36.7.

Normal: 24.86
Surprise: 41.24
116d6Reliable TalentRT: “Whenever you make an ability check that lets you add your proficiency bonus, you can treat a d20 roll of 9 or lower as a 10.”Hare-Trigger: “You can add your proficiency bonus to your initiative rolls.”

Oh no, they interact. We can’t get lower than 24 for Initiative checks now. We’ll always have something to shoot in round one.
126d6Feat: Inspiring LeaderWe got the Charisma and we’re just filling out our feats. It’s a solid feat, too, adding between 60 and 90 hit points per rest depending on the size of your party at this level.
137d6ImpostorThis is like Infiltration Expertise, except we get to be a specific person instead of making up a new one.

Again, there might be some good ways to generate Surprise with this feature if you’re creative. Just don’t try to overdo it.
147d6BlindsenseNo more Invisible foes (within 10 feet anyways).
158d6Slippery MindWisdom Save Proficiency. It’s nice.
168d6Feat: Resilient Constitution +1 (16=>17)Constitution Save Proficiency. Also nice.

There are other options, but this is just for the fun of having the big three saves. Also so we can get out if we somehow botch an Assassination.
179d6Death StrikeThis is great if we can pull off Surprise. Surprise can be difficult, but if you’ve bringing an Assassin all the way to 17, you must be pretty confident in your party’s ability to get Surprise at least once per day.

We’ll throw in one more DPR calculation here, but we have to add a third entry. Death Strike doubles the damage if the target fails a Constitution saving throw. We’ll assume that monsters make that save about 60% of the time. That means we’ll be multiplying the Surprise damage by 40% to get our Death Strike value.

Target DPR at this level is 27.1, high is 54.2, and we’re starting to approach Dude Stop territory if we get a Death Strike.

Normal: 38.51
Surprise: 65.81
Death Strike: 26.324
Total on a Surprised target: 82.13
189d6ElusiveNobody gets Advantage on us. Advantage is our trick.
1910d6Feat: Durable Constitution +1 (17=>18)We’re just rounding out our Constitution and making Short Rest healing more reliable. Hopefully the Inspiring Leader feat has encouraged more short rests from the team.
2010d6Stroke of LuckWin instead of Lose once per rest.