Assassin (5A)

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You focus your training on the grim art of death. Those who adhere to this archetype are diverse: hired killers, spies, bounty hunters, and even specially anointed priests trained to exterminate the enemies of their deity. Stealth, poison, and disguise help you eliminate your foes with deadly efficiency.

Source: Player's Handbook

Subclass Features

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain proficiency with the disguise kit and the poisoner's kit. When you select an expertise at level 2 and 6, you can select either of these in addition to the other options.

Assassinate

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit. Note: A creature stops being surprised when its initiative comes up, even when it is not allowed to act.

Poisoner

At 9th level, you have learned how to create and use poisons. Whenever you finish a long or short rest, you can use a poisoner's kit to create a deadly poison. The creation may be an ingested or injury poison (your choice) and lasts for 24 hours or until used. Once you create a poison this way, you may not do so again until you complete a long rest.

Assassin's Death (Ingested or Injury): A creature subjected to this poison must make a Constitution saving throw DC = 8 + your proficiency bonus + your Intelligence modifier. On a failed save the creature takes 1d12 damage for every 5 levels you have in this class and gains the poisoned condition for one minute. If the poison is ingested, the creature is also incapacitated while poisoned this way. If the saving throw is successful, the creature takes half damage and suffers no additional effects.

Infiltration Expertise

Starting at 13rd 9th level, you can unfailingly create false identities for yourself. You must spend seven days one day and 25 gp to establish the history, profession, and affiliations for an identity.

For example, you might acquire appropriate clothing, letters of introduction, and official- looking certification to establish yourself as a member of a trading house from a remote city so you can insinuate yourself into the company of other wealthy merchants.

You can 't establish an identity that belongs to someone else. To do so you must spend at least three hours studying these three components of the person's behavior, listening to speech, examining handwriting, and observing mannerisms.

Thereafter, if you adopt the new identity as a disguise, your ruse is indiscernible to the casual observer. Other creatures believe you to be that person until given an obvious reason not to.

In addition, whenever you make an ability check to create a disguise or to deceive a creature by assuming a false identity and roll less than 10 on the d20, calculate the result as if you rolled a 10. Your passive value for these checks increase by 5.

Designer's Notes

Infiltration that is almost certain to succeed feels like a high-level ability, so I merged the two disguise abilities into one. That opened a slot at level nine, where I put a poisoner ability Treeantmonk introduced for his version of this subclass.

Impostor

At 13th level, you gain the ability to unerringly mimic another person's speech, writing, and behavior. You must spend at least three hours studying these three components of the person's behavior, listening to speech, examining handwriting, and observing mannerisms.

Your ruse is indiscernible to the casual observer. If a wary creature suspects something is amiss, you have advantage on any Charisma (Deception) check you make to avoid detection.

Death Strike

Starting at 17th level, you become a master of instant death. When you attack and hit a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, double the damage of your attack against the creature.