Rogue
Base Class: Rogue

Many rogues walk a fine line between life and death, risking their own lives and taking the lives of others. While balancing on that line, some rogues discover a mystical connection to Death itself. These rogues take knowledge from the dead and darkness, immersing themselves in negative energy, eventually becoming something akin to shadows. Thieves' guilds value them as highly effective information gatherers and spies.

Many shadar-kai of the Shadowfell are masters of these dark arts, and some are willing to teach the path. In places like Thay in the Forgotten Realms and Karrnath in Eberron, where many necromancers enact their craft, a Shadow can become a wizard's confidant and right hand. In temples of death, the Shadow might work as an agent to track down those who try to cheat the grave and to recover knowledge that might otherwise be lost to death.

How did you discover this dark power? Did you sleep in a graveyard and awaken to your new abilities? Or did you cultivate them in a temple or thieves' guild dedicated to a deity of death?

Whispers of the Grave

3rd-level Shadow feature

Echoes of those who have died cling to you. Whenever you finish a Short Rest or Long Rest, you can gain proficiency in one skill or tool of your choice, as a dark presence shares its knowledge with you. You lose this proficiency when you use this feature again.

Wails of the Dead

3rd-level Shadow feature

As you nudge someone closer to death, you can channel the power of the grave to harm someone else as well. Immediately after you deal your Sneak Attack damage to a creature on your turn, you can target a second creature that you can see within 30 feet of the first creature. Roll half the number of Sneak Attack dice for your level (rounded up). The second creature takes Force damage equal to the result, as wails of the dead sound around them for a moment.

Once you use this feature, you cannot use it again until you finish a Short Rest or a Long Rest.

Tokens of the Lost

3rd-level Shadow feature

When a life ends in your presence, you're able to snatch a token from the departing soul, a sliver of its life essence that takes physical form: as a reaction when a creature you can see dies within 30 feet of you, you can open your free hand and cause a Tiny trinket to appear there, a Soul Trinket. The DM determines the trinket's form or has you roll on the Trinkets table in the Player's Handbook to generate it.

You can have a maximum of 2 Soul Trinkets at a time, and you can't create one while at your maximum. The maximum number of trinkets you can have increases to 3 when you reach level 9, to 4 when you reach level 13, and to 5 when you reach level 17.

You can use soul trinkets in the following ways:

Wailing Soul. When you deal Sneak Attack damage on your turn and you have already used your Wails of the Dead feature, you can destroy one soul trinket that is on your person to use it again.

Speak with Spirit. As an action, you can destroy one of your Soul Trinkets, no matter where it's located. When you do so, you can ask the spirit associated with the trinket one question. The spirit appears to you and answers in a language it knew in life. It's under no obligation to be truthful, and it answers as concisely as possible, eager to be free. The spirit knows only what it knew in life, as determined by the DM.

Spirit of Protection

9th-level Shadow Feature

Your vitality is enhanced by your connection to the dead, enhancing your being in the following ways:

Ghostly Vitality. While a Soul Trinket is on your person, you have Advantage on Death Saves and Constitution saving throws. 

Minor Exorcism. You can use your action to target an ally you can see within 30 feet of you and destroy a Soul Trinket that is on your person to end one effect on that creature causing it to have the Charmed or Frightened condition, or an effect causing it to be possessed.

Screams of the Dead. When you use your Wails of the Dead feature, you can target 2 additional creatures instead of 1 to deal Necrotic damage to.

Shadow Walk

13th-level Shadow feature

You can phase partially into the realm of the dead, becoming like a Shadow. As a Bonus Action, you assume a Shadowy form. While in this form, you have a Fly Speed of 10 feet, you can hover, and attacks have Disadvantage against you. You can also move through creatures and objects as if they were difficult terrain, but you take 1d10 Force damage if you end your turn inside a creature or an object.

You stay in this form for 10 minutes or until you end it as a Bonus Action. To use this feature again, you must finish a Long Rest or destroy one of your Soul Trinkets as part of the Bonus Action you use to activate Shadow Walk.

Death’s Will

17th-level Shadow feature

Your association with death has become so close that you gain the following benefits:

Shrieks of the Dead. When you use your Wails of the Dead, you can now target 3 creatures instead of 2, and one of these creatures can be the original target of the Sneak Attack.

Call Upon the Fallen. At the end of a Long Rest, a Soul Trinket appears in your hand if you are missing any of your Soul Trinkets, as the spirits of the dead are drawn to you.

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