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Class: Rogue: Assassin
Practice the Grim Art of Death An Assassin's training focuses on 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
All that waiting. First move is yours.
You're adept at ambushing a target, granting you the following benefits.
You have Advantage on Initiative rolls.
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
Either way, you are getting in.
You gain a Disguise Kit and a Poisoner's Kit, and you have proficiency with them.
Level 9
Prepare to improvise
You are an expert at the following techniques that aid your infiltrations.
You can unerringly mimic another person's speech, handwriting or both if you have spent at least 1 hour studying them.
Your speed isn't reduced to 0 by using Steady Aim.
Level 13
Preparation is half the job
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
First move. Game over
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 plus your Dexterity modifier and Proficiency Bonus), or the attack's damage is doubled against the target.