D&D 5e: Serpentkin Roguish Archetype 3

A few months ago, Jeremiah McCoy mentioned wanting a snake-themed roguish archetype, inspired by his long-term King’s Gate character who was a physician and brewer with a bond to the Snake totem. Obviously, barbarians are the class with pre-existing totemic themes, but I wouldn’t be sorry to see totemic themes extended to other classes. Other than Rich Howard’s Alchemist class (which I heartily recommend), a roguish archetype is definitely the best fit for what I wanted to do.


Serpentkin (Roguish Archetype)

Some rogues swear themselves to strange and squamous gods or dark powers. Others are dedicated to the totemic spirit of the Snake or came into contact with a single drop of blood from the World Serpent. With training, they can develop venom and gain great control over it, as well as other powers common to mythic serpents.

Serpent’s Maw

When you choose this archetype at 3rd level, you learn to speak, read, and write Draconic. You can use this language to speak to and understand snakes of all kinds.

Your canines becomes fangs, and you can express venom through them. While you have a weapon or projectile that deals piercing or slashing damage in hand, you can use a bonus action to coat it with venom. The next time you hit a creature with that weapon or projectile, it rolls a Constitution saving throw. On a failed save, it is poisoned until the end of your next turn. You can use this feature once, and regain use of it when you finish a short or long rest.

Serpent’s Skin

Also at 3rd level, you gain fine scales over your arms, legs, and torso. You can choose whether these scales also cover your face, neck, hands, and feet. While you are not wearing armor, your AC equals 10 + half your proficiency bonus + your Dexterity modifier.

Further, you gain resistance to poison and advantage on saving throws against the poisoned condition.

Shed Skin

Beginning at 9th level, you can shed damaged scales and rapidly heal your wounds. As a bonus action, you can expend a hit die and regain a number of hit points equal to the result plus your Constitution modifier or Charisma modifier (your choice). You can use this feature once, and regain expended uses when you finish a short or long rest.

Further, you regain additional Hit Dice equal to your Constitution modifier or Charisma modifier (your choice) when you finish a long rest.


Starting at 13th level, small doses of your venom can balance out the humors of your patients and quicken their healing. As an action, you can touch yourself or another creature and choose one of the following:

  • The creature can make a new saving throw against one disease that is affecting it.
  • The creature ends one blinded, paralyzed, or poisoned condition that is affecting it.
  • The next time it regains hit points before the end of your next turn, it regains additional hit points equal to half your rogue level.

You can use this feature a number of times equal to either your Constitution modifier or Charisma modifier (your choice), and regain all expended uses when you finish a long rest. Constructs and undead can’t be affected by this feature.

World Serpent’s Spawn

Beginning at 17th level, your venom becomes much deadlier. You can use your Serpent’s Maw feature 3 times, and regain all expended uses after 1 minute.

When you use your Serpent’s Maw feature, you deal an additional 4d6 poison damage.

Further, you can also modify your poison to be acidic or neurotoxic, as a bonus action. While your Serpent’s Maw feature is an acidic toxin, your weapon instead deals 4d6 acid damage. While your Serpent’s Maw feature is neurotoxic, your weapon instead deals 2d6 psychic damage, and the creature rolls a Wisdom saving throw. On a failed save, it is paralyzed until the end of your next turn.


Design Notes

Not to put too fine a point on it, but I’ve been struggling with the core mechanic of this subclass for a couple of months now. At first I wanted to use a pool of venom points (per long rest) that they’d expend for poison damage and healing effects. Earlier today I tried something more like Combat Superiority dice (so per short rest). I liked how that looked even less. Don’t get me wrong, I love the crap out of ki points and Battle Masters; it was just too obvious to me that I was being lazy.

It may be weird that they don’t improve their damage output until 17th level, but the poisoned condition is a serious (if short-term) debuff that should help the party a good bit. If I were to change anything about Serpent’s Maw, I’d increase its frequency of use, because some number of misses on a per-short-rest feature means that it’s fairly limited.

Shed Skin is a pretty direct lift from King’s Gate, but also possibly a nice survivability boost for rogues.

Asklepian is all about the mythic meaning of serpents, of course. I hope it’s fun for rogues to offer a “healing received” buff, which they can use on themselves to trigger with their Shed Skin feature or a healing potion.

World Serpent’s Spawn touches on a concept I put into one of my early-early 5e feat designs, where you can turn a poison into a caustic agent or a neurotoxin to get around poison/poisoned immunity. I did also want Serpentkin to deal additional damage, so it shows up here.

My big design question is how much extra damage it’s okay for rogues to derive from their subclass in ways that they can easily, reliably trigger (as compared to the unreliability of Assassin damage boosts). I can imagine retuning World Serpent’s Spawn (and maybe Serpent’s Maw) extensively. If you’re especially wise in the ways of roguish archetype design, talk about it in the comments.

I have a lot of features use either Constitution or Charisma, because I couldn’t justify using Dex. I think either physical resilience and control or mystical connection suit the Serpentkin theme pretty well, but at the same time I get that it’s a little weird. Allowing either of the two options is my half-nod to avoiding multiple attribute dependency. After all, rogues probably want good Con or Cha anyway.

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3 thoughts on “D&D 5e: Serpentkin Roguish Archetype

  • Craig Cormier

    I’m happy to see someone leaning into the mythological connection between snakes and healing. It is all to often overlooked.

    The 2 level 3 abilities both immediately put me in mind of the transmutation experiments and changes that yuan-ti are often associated with. Makes me think that a series of sub-classes that are specifically about a character’s connection to a specific monster or group of monsters might be fun. There was a great series of articles in the 3rd edition era of Dragon Magazine that had prestige classes for characters tied to things like beholders, mind flayers and the tarrasque. All of which granted strange physical transformations in addition to fun powers.

  • Raymond Cook

    I think you have the workings of a viable archetype here and like that you went wide with the AC and healing as part of the serpent theme as well. Regarding damage balance, you are good in shape here with the early venom application focusing on control and moving into damage at 17th level. The two published comparison points that come to mind here would be Assassin and Swashbuckler. For Assassin damage is frontloaded into the Assassinate surprise attack feature, which is intended to only come into play once per encounter and is therefore rather balanced over the course of the encounter. Alas, many people are confused about whether surprise rounds exist in 5e and if so would you get Assassinate for that entire round if it were a thing at all…and still more people seem to think that attacking from stealth gives you a surprise attack (it’s a cute notion really..) So compared to a relaxed/misread rules played Assassin, Serpentkin will be very balanced on damage. Okay, so that was a silly comparison and mostly a rant against some rule misunderstandings that I’ve had to explain to PCs… swashbuckler… getting sneak attack without advantage or a nearby ally so long as it’s just you and the baddy going toe-to-toe at just 3rd level is pretty great – situationally great but also thematically great! Soooooo that being said I like inflicting Poisoned here with limited early level uses vs. straight damage output early. In a well run dumgeon delve or adventure, even non-assassin rogues will find an opportunity to get in a few big sneak attacks and feel great about their class. I believe you mentioned this exact thing in your Aurikesh write-up of the Nightwalker’s fingers quest. Now for a Homebrew to Homebrew comparison… I’ve been working on tuning a Master of Poisons archetype for a while now and I’ve had the opportunity of having a playtester provide feedback on the evolution. In the early drafts, at 3rd level the rogue could apply poison to their blades for bonus 1d4 poison damage and that scaled up with levels. We both felt that the damage was scaling far too quickly when coupled with sneak attack. After all, there’s a reason for the relatively gradual scaling of sneak attack dice…in the second draft I went the route of saving throw against poison and bonus damage on failing by 5 or more. Poisoned felt like an interesting control mechanic in early encounters but the additional damage on bad fails was a pain for both of us to remember and I’ve always hated those sorts of mechanics anyway. In later revisions, the focus has shifted toward knowledge of and ability to craft many different poisons for differing control effects. For example, the rogue may choose from a list of known poisons at 3rd level, including Crippling Poison (save against move speed reduction), Weakening Poison (save against strength reduction), etc. At higher levels, I introduced poisons like Mind Numbing Poison (effectively Slow via a melee attack) and, like Serpentkin, a feature to treat attacks as non-physical damage (acid/necrotic) for the purpose of overcoming resistances. Options to take damaging poisons also existed but we both felt that good situational use of the control poisons made for more engaging gameplay overall. So again, cool that you are not pouring features into damage early for Serpentkin. So far my playtests have been over short adventures or one-shots with little room for playing up the Exploration pillar of a Poisoner archetype – i.e. needing to research new poisons and gather/buy the appropriate ingredients but I can see that developing into a facet of the archetype. I expect that you’d be able to similarly focus PC development on learning more about the World Serpent or experience with venoms in the wild. In contrast, what do Assassin rogues have for story? A mentor who teaches them how to be more backstabby until they eventually go full cliche and murder the mentor to become master of the assassin’s guild? Yeah, cool story, bro…ahem, sorry for the rambling…