Practice the Grim Art of Death.

Assassin

Practice the Grim Art of Death

You prefer to deal sublime punishment to a single foe at a time - not in a duel, mind, because a duel implies chivalry, and you're too busy getting the job done for honour

An Assassin's training focuses on the grim art of death, using stealth, poison, and disguise to eliminate foes with deadly efficiency. While some Rogues who follow this path are hired killers, spies, or bounty hunters, the capabilities of this subclass are equally useful for adventurers facing a variety of monstrous enemies.

Level 3: Assassinate

You are adept at getting the drop on a target, granting you the following benefits:

Initiative You have Advantage on Initiative rolls.

Surprising Strikes During the first round of each combat, you have Advantage on attack rolls against any creature that hasn't taken a turn. If your Sneak Attack hits any target during that round, the target takes extra damage of the weapon's type equal to your Rogue level.

Level 3: Assassin's Tools

You gain proficiency with the Disguise Kit and Poisoner's Kit.

Level 9: Infiltration Expertise

You are expert at the following techniques that aid your infiltrations.

Masterful Mimicry You can unerringly mimic another person's speech, handwriting, or both. if you have spent at least 1 hour studying them.

Roving Aim Your Speed isn't reduced to 0 by using Steady Aim.

Level 13: Envenom Weapons

When you use the Poison option of your Cunning Strike, the target also takes 2d6 Poison damage whenever it fails the saving throw. This damage ignores Resistance to Poison damage.

Level 17: Death Strike

When you hit with your Sneak Attack on the first round of a combat, the target must succeed on a Constitution saving throw (DC 8 + your Dexterity modifier + your Proficiency Bonus), or the attack's damage is doubled against the target.