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.
As a quick note, one of the problems with the Assassin is that when it runs on full cylinders, it’s still not matching the damage output of easier, more versatile characters. It’s not easy to play an Assassin effectively because it relies on several of D&D 5e’s more complex rules: hiding, surprising, etc. Since it’s not easy to play, the Assassin should have a greater payoff for the hard work it requires.
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 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 piece of ammunition as a bonus action instead of an action.
Studying social 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*).
I actually ran the DPR calculations for the Rogue vs. my revision of the Assassin (see below). My revision leads to what is essentially +10 damage at level thirteen, scaling to +15 at level twenty. These calculations assume the use of a hand crossbow, scaling monster AC as the character levels up, and a slightly scaling Dex modifier. Here is the shocking part: even with the damage boost I’ve given to the Assassin, it still doesn’t exceed Treantmonk’s Warlock baseline for what is good damage (Eldritch Blast + Agonizing Blast + Hex). That’s right, this damage increase is not a big deal. It might gain an advantage over the baseline when poisons are considered, but poison damage potency is highly dependent on the monster type.
Here is how the calculations look in the first round of combat where the Assassin can automatically crit on a hit against surprised creatures. I did not account for whether the Assassin’s Initiative roll is higher than the target’s. The damage boost becomes more like +20 scaling to +25 (approximately). Damage ramps up again when the character reaches level seventeen to gain Death Strike. To account for Death Strike, I assumed a 40% chance of success since monsters often have high Constitution saving throws bonuses at high levels of play:
When considering Death Strike in the table above, we see that the average damage increase at level seventeen and up is approximately +30 over the PHB Assassin’s DPR. Additionally, it should be noted that using the Warlock as a baseline with its Eldritch Blast + Agonizing Blast + Hex may not be the best comparison because the Warlock doesn’t have the reliable method to gain advantage like the Rogue does with Steady Aim (new feature from Tasha’s that every Rogue should use).
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.
You can reference my second spreadsheet image in the Just Business section above to see the DPR when Death Strike is included.
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:
- Feats for Rogues
- Rogue Multiclassing Guide
- Rating Rogue Subclasses
- Rogue + Fighter Character Concepts
- Rogues Using Mounts
- Selecting Arcane Trickster Spells
- Sneak Attack Tactics
- Rogues as Benevolent Criminals
Check out my video about how surprise works in D&D 5e if my Assassin revision made you wonder about it: