Rogue Assassin Homebrew Fix: D&D 5e Revision

D&D 5e Assassin Rogue homebrew revision featured art is by 000fesbra000. Creative Commons License.
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The Assassin is a Rogue subclass I want to love, but it has severe flaws. Surprising enemies can be difficult for players to achieve, and that goes double for new players. I don’t know a player who doesn’t love to get critical hits, so the Assassin should be one of the most fun roles in the game. I have reworked this Roguish Tradition to better function as an executioner who uses steel, poison, and infiltration to snuff out a target and live to collect the bounty.

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.

Revised Assassin DPR vs Vanilla Rogue DPR baseline
The vanilla PHB Rogue (no subclass) vs. Revised Assassin Rogue DPR.

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:

Surprise round DPR for vanilla PHB Assassin vs Revised Assassin.

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.

Change Log

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

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

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

What Do You Think?

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

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

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

Check out my video about how surprise works in D&D 5e if my Assassin revision made you wonder about it:

22 thoughts on “<b>Rogue Assassin Homebrew Fix</b>: D&D 5e Revision”

  1. No only no, but Hell No!
    This is absurdly OP. Bad enough when you seemed to want Imposter at 9th rather than 13, but with the addition too it is blatantly ridiculous! And if that were not enough, what you want to do with sneak attack dice, doesn’t bear commenting.

    1. Hi expDM, I would love to discuss this with you to see why you think this is OP. I know you said it’s not worth commenting, but I’d welcome the back and forth to see if I want to change anything. Maybe your experience with the Assassin by RAW has you coming from a place where you think it doesn’t need revision?
      What I did with Sneak Attack dice at level 13 is, on average, a damage boost to each Sneak Attack rolled by 1.375. At level 13, that’s an average damage boost per turn of seven dice for 9.625 average damage increase per turn. 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 subclass I’m working on here.
      The level 9 and 13 abilities are notoriously underwhelming for a variety of reasons that I mentioned in my Rogue subclass ratings article. I am intensely curious as to why you suggest it’s OP to combine those.
      I’d love to hear more of your thoughts to refine my 5e revisionist skills. 🙂

      1. I think it’s great! I DM for a assassin rogue and agree that the 9th and 13th abilities are very underwhelming, so to give a more assassins creed flavor to the class I gave multi-attack at 9th level and also did an initiative bonus based on intelligence. Seems to work great, doesn’t make the class OP in my campaign. Idk why the guy thinks the imposter feat make this class OP cuz it definitely is NOT in the base class haha.

        1. Thanks, Tombstone023! I enjoyed reworking this subclass, and I see that you enjoyed the same project. Gaining Extra Attack at level nine seems like a harmless change to make the class more consistent with its ambush attacks; great idea.

  2. I love this. It’s much more powerful, sure, but honestly not more powerful than an arcane trickster. The features you’ve augmented and replaced were carefully thought out and, by my estimation, balanced. I particularly love the initiative boost and the application of poison. The extra damage at level 13 is a nice bump as well.

    Also, the Assassin really does need some love. When you play a rogue and pick Assassin, you don’t expect to find such a halfhearted subclass. You picked Assassin because you wanted to feel awesome and deadly. Your version does a much better job of this.

  3. I like your idea to change some “bad” features of the assassin, but i think you overdid with something, I’ll relate based on each level.
    3. Tricks of the Trade, i like the proficency bonus to initiative, even if it kinda replace something from the Alert feat, which make me worried about an assassin with this rework and the feat, but i don’t think you can have proficency in it… you should simply say “you add your proficency to initiative rolls”.
    3. Assassinate, not ok with the poison part as bonus action, it is already in the poisoner feat.
    9. Infiltration Expertise, same as the previous one, too much from the actor feat, but i like the sleight of hand part.
    13. Just Business, ok with dice change, but i would simply reroll 1 or 2.
    17. Death Strike, ok with changes, and as many features of the assassin, is particularly relevant at first turn.

    So, i like the idea, but it take to many (already strong) part of some of the strongest feats for rogue (actor, alert and poisoner). I would change some of its features. This look like an attempt to put 3 feats in a subclass kit.

    1. Hi Reminas, thank you for outlining your thoughts clearly!
      It sounds like you don’t like it when feat benefits are mimicked by subclass features. I admittedly don’t share that concern, but I’ll go through them.
      The Actor feat was actually overshadowing BOTH Assassin features at levels nine and thirteen in RAW. It’s common to see those features as negligible or pathetic. I didn’t really change them, but I did combine them. RAW had the features already competing with Actor.
      The Swashbuckler is a well-loved Rogue subclass, but it similarly overlaps with the Mobile feat with its Fancy Footwork feature. That’s my favorite part of the Swashbuckler.
      The Poisoner feat is only partially overlapping with this bonus action to apply poison. I don’t think a subclass that is designed to enable the poisoning of weapons and such should be dependent on a feat that came out more than five years after the game launched; I certainly don’t think a revision should be limited by the feat overlap. In fact, I take that as a point toward it being an ok design change because it already exists elsewhere in the game. It’s common to ask myself if there is precedent for an ability I invent; if there is, I feel more comfortable with it. For example, crafting poisons and disguises at half the cost and time resembles the savant abilities of the PHB Wizards copying spells to their spellbooks.
      Could you explain why you view overlap with a feat as a deal-breaker for a subclass design? There are even feats themselves that overlap with each other (Crossbow Expert and Gunner).
      You’re right about the Initiative wording for the proficiency bonus. I’ll update that.
      I’m glad you like the Sleight of Hand for poisoning! I think it’s a nice “touch”. 😉
      I suspect Just Business is my most controversial change, so I’m pleased that you like it. I’ll explain why I went with the minimum roll of 3 instead of rerolling 1s and 2s. I did extensive math (more than I usually bother with) to compare two Fighting Styles in the past, Duelist and Great Weapon Fighting. I found that Duelist is statistically better, partially because rerolling 1s and 2s can still result in another 1 or 2. I’ve also heard from WotC designers that they’re hesitant to make dice rerolling abilities due to them slowing the game down for all the dice to be resolved. It’s not a huge concern, but I do keep it in mind. I’m open to changing this feature, but I haven’t decided how, yet.
      Thank you again for your thoughts! I’d welcome any follow-up thoughts you have. I can be convinced to revise the revision. 😛

      1. Soo… I read again the subclass, both. As you say, fancy footwork emulate 1 part (the strongest part) of the Mobile feat.
        Going back to what i already said, at lvl3 the bonus action to poison a weapon isn’t a big deal, but i would focus more on fixing poison. Basic poison last 1 minute and deal 1d4 damage each time you hit and the poison from poisoner work only until you hit a creature so, even if it does more damage (2d8), it last for 1 minute or until you hit. So this change isn’t a big deal. The one thing i would add is that you can apply poison as a bonus action only to a weapon you are holding, so is limited to you and it looks less similar to the feat.
        At lvl9 to balance the need for some feat, i would keep the advantage only on deception or switch it to expertise, or make deception with both intelligence and charisma (because int is a better stat for assassin). The Actor feat gives advantage to deception and performance, but this gave advantage in every charisma check, which is 2 more skills.
        While i wrote my first comment i realized that with your change to lvl13 feature, count 1 and 2 as 3 is something like “balancing stuff”, but only if you keep the d8 damage for Sneak Attack, so if you keep d8, 3 damage minimium is good, but if you keep d6 i would count 1 as 2, to keep it less then half dice.
        For the part about overlapping feats, the 2 you mentioned don’t properly overlap, cause the gunner feat doesn’t let you attack with a bonus action, which is one of the best part of crossbow expert.
        In conclusion, i’m mostly ok with your changes, but as i wrote, with mine you keep the need for feats to a class which would pick them either way. In my balancing method, if a class get something from a feat (but isn’t stronger), would benefit from taking the feat. A swashbuckler with mobile is really strong, but your changes kinda outrun feats.

        1. This makes sense and I like a lot of your ideas. I’m most intrigued by your suggestion to utilize Intelligence for what usually would be a Charisma check. I’m going to meditate on this and rework the level nine. I’m thinking I’ll keep the level thirteen as I have it, but maybe I’ll try a play test to make sure it works as intended. Thank you for your input!

          1. Thx I’ll wait for your test, i really like assassin, but it was like a solo campaign class. Lvl13 ability is ok for me, this is an assassin, i think is logical that it’s sneak attack deal more damage.

  4. Christopher Connelly

    Fantastic suggestions! I mainly play rogue in campaigns as it is my favorite class, and this actually makes assassins worth playing and not so niche as they currently are. As it stands, the dm really has to go out of their way to make your features as an assassin relevant, and that feels bad as a player imo. Thanks for this, as well as all the other great articles! Hopefully wotc implement these changes or very similar ones.

    1. Thank you, Christopher! You described my goal with this revision, so that makes me feel like I succeeded. And thank you for the compliment on our articles overall.

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

    Pump the breaks on this train. You got me scratching my head on how applying the poison as a bonus action. Can you give a citation on that? PHB or any other book?
    Though this one point has be befuddled this is a great write up.

    1. Hi A A Ron,
      This is a revision, so it’s not in any book. If you’d like a precedence for a bonus action poison application, see the Thief’s Fast Hands or the Poisoner feat in Tasha’s Cauldron of Everything.

  6. Fullmetal Potato

    Love this rework, my suggestions though would be this.
    1. I would either remove the poison stuff from tools of the trade or remove the bonus to initiative from Assassinate. While some class features mimics feats, I don’t think that class features at the same level should mimic two at once on top of the other things those features provide. I would remove the poison stuff as its more flavorful and less integral to the major function of the subclass. That way poisoners can choose the poisoner feat and not worry about getting alert since the subclass already gives it. Or you can take both away to balance out the suggestion I have below.

    2. For Just Business, I think you could keep the sneak attack dice as d6 only count ones as twos, but in return, you get this:
    If you roll an attack with advantage and both rolls would hit, the attack is treated as hitting a surprised creature for the purposes of this subclass’s features.

    Now you get a way of proccing Assassinate and Death strike outside of the first round, or a way to do it if you fail to surprise them. This change is meant to show that if a target is easy enough to hit, you don’t even need to get the drop on them to hit their most vital spots. I think this change helps them be less of a 1 trick pony.

    1. Thank you for the feedback Fullmetal Potato!
      1. A consistent bit of feedback has been a concern of overlap with feats. I’m not sure why this is a concern, to be honest. If you can articulate why this is a concern, I’m open to figuring it out, but it’s not something I inherently understand. I imagine anyone using this subclass revision can choose if they’re going to keep both the initiative bonus and the poisoning perks, so I’d rather keep it as I’d allow it to be played and let people pick and choose from it. Now that it has been a while, I’m realizing that more and more initative bonuses are being added to the game, so I’m a little leery of it stacking with other perks.
      2. It’s funny that you say that because I actually considered the surprise/crit perks based on rolling advantage and hitting with both. I ended up deciding it was more powerful than I was comfortable with, but it’s a really cool idea.
      Let me know if you have more thoughts! 🙂

      1. I think the main reason you’re seeing that feedback is that people dislike “dead” features. If a player wanted to make a poison-focused assassin, RAW they could get the Poisoner feat and gain three useful features. With this homebrew, however, while an assassin might still want to get the feat for the improved poison and ignoring resistance to poison damage, an entire third of the feat becomes redundant, which just isn’t a good feeling. As a DM, of course, I don’t care too much. I can just add a benefit to either subclass or feat for characters that get bonus action poison application from another source, like “You can split poisons with minimal loss in efficacy. When you apply poison to a weapon or piece(s) of ammuniton, you can apply that poison to twice as many weapons or pieces of ammunition. If you do so, the poison retains its potency for half as much time or half as many hits (min. 1).”

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