Master of Shadows

Special thanks to Bondye's Assassin Variant: Master of Shadows. This is based off that variant but a couple twists to ensure level playing field. --- As a Master of Shadows, you have honed your ability to blend into the darkness and become one with the shadows themselves. Your movements are stealthy and precise, allowing you to slip past even the most vigilant guards unnoticed. You are an expert at using the shadows to your advantage, both as a means of concealment and as weapons/utilities. Your attacks are swift and deadly, and you can strike from the darkness with deadly accuracy. Your mastery of the shadows allows you to strike fear into the hearts of your enemies, and your reputation as a shadowy figure is well-deserved. Whether you are sneaking through the streets on a covert mission or unleashing devastating attacks from the shadows, you are a formidable opponent and a force to be reckoned with.

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.

Always Prepared

When you choose this archetype at 3rd level you also gain the ability to, as a bonus action, create an object of hardened shadow. This construct can take the form of your thieves tools, daggers, and a bow + quiver. Objects created with this feature fade back to shadow when they leave the hands of the shadow assassin. Rogue can bond with up to 2 existing items to pull in and out of the shadows with a bonus action and it will not disappear when leaving the hands. This bond changes the look of the item to the shadowed construct. 

The shadow construct is made of a smoky, shadowy substance that is both solid and intangible at the same time. It is as durable as any other object of its kind, but it is also able to dissipate into smoke at a moment's notice. This allows you to use the shadow construct for a variety of purposes, such as picking locks, disarming traps, or even attacking enemies.

Shadow Step

At 9th level, you gain the ability to step from one shadow into another. When you are in dim light or darkness, as a bonus action you can teleport up to 60 feet to an unoccupied space you can see that is also in dim light or darkness. Upon Teleport, you create a wisp of black shadow smoke and will need to re-roll any stealth check with advantage. If currently engaged in combat, will not be able to use this power until fully disengaged. Teleporting across difficult terrain will require an acrobatics roll with advantage; If failed, user teleports half way and takes 1d4 damage on landing. 

Dark Awareness

Starting at 9th level, your connection with the shadows allows you to be ever vigilant. You remain aware of your surroundings within 30ft, even while asleep, shadows watch over you. In addition you can never be surprised and can take your turn normally in a surprise round.

Shadow Projection

At 13th level you gain the ability to project your shadow to any location on the same plane of existence that you are familiar with in which your mark has been made with charcoal, or within 20 feet of a creature that carries your mark. The target location must be in dim light or darkness. As an action you may cast your senses into your shadow self but are blinded and deafened to your physical surroundings. You may speak through your shadow. You may end this at anytime with no action required. In addition a creature may request your shadows presence by being in contact with your mark and focusing on their desire for contact for 1 minute. You are not required to respond in any way but you are aware of the request.

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.