Assassin

With extreme care, a slender elven man transfers the contents of a flask into several smaller vials. Placing the vials in a specially-made bandolier across his chest, he climbs out the window and disappears into the night. He will not return until his mission is complete.

A sudden scream pierces the festive atmosphere of the dining hall. "The baron! He needs a healer!" During the commotion that follows, a young woman - dressed as one of the serving staff - ditches the platter of hors d'ouvres on a nearby table and makes for the exit, smiling at the thought of the reward that awaited her for fulfilling the contract.

The assassin is a rogue who uses vicious poisons to their benefit in combat. They are masters of infiltration, preferring sudden strikes with hidden weapons before quickly disappearing into the night.

When you make an assassin, you should consider who you work for and your preferred methods. Some assassins form covert brotherhoods with an organized contract system, others are freelancers - increasing both the risk and the reward. You might even be in the employ of a monarch or other polity, working in the shadows to eliminate those who threaten their power.

As per methods, perhaps you silently stalk the rooftops for your prey, waiting for the perfect moment to deliver death from above. Maybe you infiltrate banquets where nobles gather and discreetly slip a vial of poison in your objective's wine glass. You might even be a bounty hunter who uses non-lethal poisons to bring your targets in alive. Regardless of your preferred modus operandi, a combination of stealth, poison, and disguise will help you dispatch your marks with ruthless efficiency.

Assassinate

3rd-level Assassin feature

The first strike is the most important, and an unaware foe is an easy kill. You have advantage on initiative checks, and on the first round of combat your Sneak Attack gains additional dice equal to your proficiency bonus against creatures who have not taken a turn yet.

Master of Poisons

3rd-level Assassin feature

Poison is your preferred method of killing, and you excel at both making and delivering these deadly concoctions.

You gain proficiency with the Poisoner's Kit. As a bonus action, you can coat a weapon or piece of ammunition with special poisons. The poison must be used within 10 minutes, or it loses its potency. The next time you hit with that weapon, you can trigger Sneak Attack unless you had disadvantage on the attack (all the other rules of Sneak Attack still apply). The damage from Sneak Attack becomes Poison for that attack, and gain additional effects depending on what poison you applied. If the poison requires a saving throw, its DC is 8 + your proficiency bonus + your Intelligence modifier.

You know the following poison formulae:

• Viper's Venom: The target must succeed on a Constitution saving throw or become Poisoned until the end of your next turn. While poisoned, their movement speed is also halved. If they fail their save by more than 5, they are also Mind Whipped.
• Nettlerue Dreamer: This poison and its delivering attack deals no damage. Roll your Sneak Attack damage twice, and if the target has fewer hit points than that, they magically fall asleep, rendering them Unconscious for 1 minute. Any damage against them ends the effect, and another creature can use their Action to shake the creature awake. If the creature has taken a turn in combat, they can make a Constitution saving throw to avoid the effect.

You can apply these poisons a number of times equal to your proficiency bonus times per long rest. You can also craft other poisons in half the time and for half the cost, and you can use your poison DC for any other poisons you find or create.

Brewer of Death

9th-level Assassin feature

You learn one additional poison formula:

• Wizardsbane: The damage from your Sneak Attack becomes Psychic, and the target has disadvantage on any Concentration checks they make as a result of this damage, and if they attempt to cast a spell before the end of your next turn, they must first succeed on an Intelligence saving throw against your Poison save DC, or the spell fizzles.

Additionally, your exposure to poisonous substances has built up some measure of tolerance. You gain resistance to Poison damage, and you have advantage on saving throws to avoid the Poisoned condition. Finally, if you deliver poison on an attack that is a critical hit, the target has disadvantage on any saving throws from the effects.

Tears of Ire

13th-level Assassin feature

You learn an additional poison formula:

• Tears of Ire: The target must succeed on a Wisdom saving throw or become frenzied and unable to tell friend from foe, attacking random creatures on their turn. The target can repeat the saving throw at the end of their turns, ending the effect on a success.

Additionally, if you trigger Sneak Attack against a Surprised target, the attack automatically becomes a critical hit.

Death's Kiss

17th-level Assassin feature

You learn an additional poison formula:

• Death's Kiss: The target must succeed on a Constitution saving throw or take half the damage of your Sneak Attack again.

Additionally, all the exposure to poisons has made you numb to their effects. You become immune to Poison damage and the Poisoned condition.