Infiltrator

Professional killers and talented socialites, Infiltrators combine a keen eye and quick reflexes with mastery of the blade, stealth, and carefully-chosen words. Glamorous assassins who must infiltrate all manner of societies, their tongues are just as sharp as their knives.

Coup de Grâce

Your blows are deadliest when your foes are at their weakest or don't realize you were ever there. Starting at 3rd level, you have advantage on initiative rolls, and on attack rolls against creatures that have not yet acted in combat. Any attack that you land against a creature that is stunned, surprised, or has not yet taken a turn in combat is a critical hit.

Tools of the Trade

Also at 3rd level, you have assembled invaluable skills for any assassin. You gain two of the following benefits.

• proficiency in Disguise Kits
• proficiency in Poisoner's Kits
• proficiency in Forgery Kits
• proficiency in one gaming set of your choice
• Two languages of your choice

If you take proficiency in a kit, you can use it, its components, or its products using your Cunning Action.

Analyze Target

Starting at 9th level, if you spend at least 1 minute observing or interacting with another creature outside combat, you can learn certain information about its capabilities compared to your own. The DM tells you if the creature is your equal, superior, or inferior in regard to two of the following characteristics of your choice:

• Intelligence
• Wisdom
• Charisma
• Class levels (if any)
• Hit Points

At the DM's discretion, you might also realize you know a piece of the creature's history or one of its personality traits.

Undercover

At 13th level, you can create a false identity by spending 3 hours considering facets of your new persona such as mannerisms, speech patterns, and clothing. If you spend at least 1 hour observing these features in an existing humanoid you can mimic that person instead. The identity also includes letters of introduction, forged certifications, appropriate clothing, etc. This disguise is indiscernible to the casual observer, and you have advantage on Charisma (Deception) checks to maintain it when questioned.

Backstabber

At 17th level, it is impossible to tell through magical means whether you are lying, and checks made to discern the truth of your statements are made with disadvantage. Magic cannot compel you to tell the truth, and your mind cannot be read through any means. The first time you damage a creature that regards you with affection or considers you an ally, you have advantage on the attack and forgo damage dice. Instead, you deal the maximum possible amount of damage.