Nightingale

When the most infamous of rogues in history decide to delve into the understanding of the Shadowfell, they become acquainted with a being known as The Mask, the diety of Thievery and Shadows. Those who in turn offer themselves to him as servants in exchange for power and fortune become a member of his honored ranks and gain abilities that enhance themselves to heights they only ever dreamed of reaching. They become avatars of his will and merge their very beings with the shadows around them. This turns the rogue into what is known as a Nightingale, a theif imbued by the shadows, and fueled by their lust for coin and power. These rogues are specialists in darkness and can tap into arcane energies to aid them in stealing riches and slitting throats alike.

Eyes Of The Night

At 3rd level, you gain darkvision out to a range of 60 feet. If you already have darkvision from your race, its range increases by 30 feet. You also gain the following benefits.

• While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

• Any spell you cast that produces dim light or darkness can be seen through clearly for yourself and all friendly creatures.

Shadow Magic

You gain the ability to use your life essence to weave shadows into arcane energy, allowing you to cast spells (with certain spells gaining added bonuses when cast while within dim light or darkness) at the cost of Shadow Points. Your total amount of Shadow Points is equal to your Nightingale level, and you regain all Shadow Points on a long rest and half of them rounded down on a short rest. Charisma is the spellcasting ability for your shadow magic.

You gain Shadow Magic spells at the levels listed.

3rd Level
Shadow Blade = 1 Point (Cost increased by 1 point for every level above 2nd this spell is cast at.)

Dim Light Bonus: Shadow Blade does not require concentration when cast.

5th Level
Darkness = 2 Points

Dim Light Bonus: Darkness cannot be dispelled by light producing magic.

9th Level
Vampiric Touch = 3 Points (Cost increased by 1 point for every level above 3rd this spell is cast at.)

Dim Light Bonus: Vampiric Touch has a range of 15 feet when cast.

13th Level
Shadow Of Moil = 4 Points

17th Level
Maddening Darkness = 6 Points

19th Level
Eclipse = 10 Points

Skeleton Key

You gain an ebony lockpick that is materialized out of energy straight from the shadowfell, and can only be seen by you when in direct sunlight. When held or taken by anyone else, the lockpick dematerializes, and reappears in your possesion an hour later. The lockpick gives you the following benefits.

• Any thieve's tool check preformed in dim light or darkness can be rollled with advantage.

• Any stealth check preformed in dim light or darkness that results in a roll of 9 or lower automatically becomes a 10.

Shifting Shadow

At 13th level, you gain the ability to hide and move within shadows to such a degree you become indistinguishable to most. You gain the following effects.

•When you are in dim light or darkness, as a bonus action, you can teleport up to 120 feet to an unoccupied space you can see that is also in dim light or darkness

• When you are in dim light you can use your action to become invisible until you move or take an action or a reaction.

Umbral Evasion

Starting at 17th level, you can evade attacks with supernatural precision and manipulate your enemies actions with a shadowlike aura.

Once per round whenever a creature makes an attack roll against you and doesn't have advantage on the roll, you can use your reaction to impose disadvantage on it. You must use this feature before you know the outcome of the attack roll.

Additionally while you are within dim light or darkness, if the incoming attack misses you can choose to make the enemy roll an additional attack against a target of your choice within 5 feet of the attacker.