This Rogue subclass seeks to harness and manipulate the very shadows themselves to their advantage. Through the forming of a connection with the Shadowfell, these Rogues can even manifest creatures of shadow to aid them in their goals.  Masters of stealth, surprise, and...not small amounts of backstabbing, those who follow this art make potent allies, or deadly enemies.

Shade Energy

3rd-level Shadowgrasp feature

The shadows cling to you, energized and ready to do your bidding. This manifestation is represented by your Shade dice, which are each a d6. You have a number of these dice equal to twice your proficiency bonus, and they fuel various shadow powers you have, which are detailed below.

Some of your powers expend the Shade die they use, as specified in a power’s description, and you can’t use a power if it requires you to use a die when your dice are all expended. You regain all your expended Shade dice when you finish a long rest. In addition, as a bonus action, you can regain one expended Shade die, but you can’t do so again until you finish a short or long rest.

Hidden Path.  For each unspent Shade dice you currently possess, you may add 1 times the number of dice to any stealth check you make.

Shadowy Aid. The shadows can be your ally, and help you succeed where others fail: if you fail an ability check using a skill or tool with which you have proficiency, you can roll up to two Shade dice and add the number(s) rolled to the check, potentially turning failure into success. If the roll does not succeed, you only expend 1 die (rounded down).

Manifest Shade. Utilizing your connection to the Shadowfell, you may call forth a creature of shadow to temporarily aid you. The creature can resemble a beast of small size, but will be made of shadowy substance. To summon a creature, you must spend 1 minute casting, then expend a Shade die. If you would like to speed up the process, you can summon the creature with a single action by expending 2 Shade dice. The creature will remain for 1 hour times your Shadowgrasp level.

The creatures hit points equal 4 times your rogue level, it goes on your initiative, and its AC equals 10 plus your proficiency bonus. It has 30ft of walking/flying speed and can not exist further than 120ft from you. It can take the Dash, Disengage, Dodge, and Help actions, in addition to following actions below.

Shadow Transference: The Rogue may cast touch spells, or make melee attacks through their Shade.

Shadowstep: As an action the Rogue may switch places with their Shade. You may then make 1 attack as a bonus action.

Shadow Armaments

3rd-level Shadowgrasp feature

You can manifest shadows into semi-solid armaments with which to attack. As a bonus action, you can manifest a shadow armament from your free hand. You may then make an attack action with that blade (a simple melee weapon with finesse, thrown, and range 60 ft.) or ranged ammunition. On a hit, replace the normal weapon attack damage with necrotic damage. You may optionally expend a number of Shade dice up to your proficiency bonus and add the dice to your damage roll as additional necrotic damage. After the attack the armament vanishes.

Shade Empowerment

9th-level Shadowgrasp feature

Your connection to the Shadowfell grows, increasing your connection to your Shade creature and allowing for extra Shade die usage:

Twilight Precision. If you make an attack roll with your Shadow Armaments and miss the target, you can roll up to two Shade dice and add the number rolled to the attack roll. If the attack roll does not succeed, you only expend 1 die (rounded down).

Shade Connection. Through the time spent forming a connection with your shade creature, you can increase its presence on the material plane. The creature can now resemble a beast of up to medium size, and you gain the ability to telepathically communicate with the creature. It can communicate in images and sounds from its awareness. Use your stats for any perception checks it performs. In addition you also gain the following action below.

Life Tap: As an action you may expend up to two Shade dice. Your Shade creature transfers the rolled number times your proficiency bonus hit points to you. Be aware that this could potentially reduce your Shade creature to 0, in which case you would need to resummon it. You cannot transfer more hit points than your Shade creature has.

Shadowy Substance

13th-level Shadowgrasp feature

Veil of Shadows. You can use your mastery of the shadows to hide others as well as yourself. As an action, you can extend your power to aid in the stealth of your allies. Expend a Shade die. You can cloak the number rolled + 1, and they gain the benefit of your stealth bonus (including unspent Shade dice) on any stealth checks made for the next hour.

Shade Substance. You draw your Shade even more into the material plane, granting you the ability to ride it, if it is size medium or larger. In addition you also gain the following action below.

Intercede: As a reaction, you can expend a Shade die and cause your Shade to teleport to your location to take the damage from the attack you were most recently hit with or the saving throw you were required to make. If the damage comes from a saving throw the Shade will take whatever damage you would have taken after you succeeded or failed.

Shadow Mastery

17th-level Shadowgrasp feature

Shade Tendrils. You can extend shadows to physically ensnare your enemies. As an action, expend a Shade die. You may ensnare the number rolled + 1. The chosen targets must make a Strength saving throw (DC equal to 8 + your proficiency bonus + your Dexterity modifier). If the save fails, the target is restrained for 1 minute and instantly takes 4d6 necrotic damage. The restrained target can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

Once you use this feature, you can’t do so again until you finish a short or long rest.

Shade Mastery. You have full mastery over your Shade, allowing it to remain in the material plane permanently until you dismiss it or it is reduced to 0 hit points. The creature can now resemble a beast of up to large size. In addition you also gain the following action below.

Attack as One: As the Shade's action you can expend 3 Shade dice to have your Shade copy an attack you made an attack roll for. You may pick your same target or a new target within the attack's range. Use the same hit result and the same damage (if the attack would successfully hit it) on the new target.