Shadow

There are some rogues that have studied the fell energies of the Shadowfell, and they have learned to harness that energy to create a powerful vial of energy from that dark plane.  Some Shadows are intelligent thieves or cunning assassins that have chosen to augment their natural skills with the fell energies of the Plane of Shadow.  Others learned these skills because they are natural denizens of the Shadowfell, such as the Shadar-Kai or other servants of the Raven Queen.  Others still simply stumbled upon the work of other Shadows and used their wit and ingenuity to reverse engineer the Shadow Vials.

Shadows use Shadow Vials in combat, smashing them on the ground at their feet to create a variety of fascinating effects.  The most obvious of these benefits is the Shadow Form.  Upon smashing a Shadow Vial, tendrils of shadowy energy emerge from the vial and coat the Shadow, making them difficult to see even on a bright, sunny day.  When used in a lightless cavern or a dim dungeon, a Shadow can become almost invisible.  Through their training, they also gain unparalleled stealth skills, able to sneak past all but the most observant guards even without their Shadow Vials.  Many train in either alchemy or poisons, finding ways to improve their Shadow Vials with their crafting skills.  As they grow in power and study their mixtures more carefully, the Shadow Vials gain many more effects.  They can create illusory decoys, which allow the shadow to sneak through even a crowded battlefield to punish enemies for letting the shadow out of their sight, dealing massive damage when enemies ignore them, which so often happens as a Shadow can appear to vanish before your very eyes.  Experienced Shadows can even create clouds of hallucinatory gasses when they smash a Shadow Vial, throwing the battlefield into complete chaos.

Many shadows are not very nice people.  They gain their powers from the negative energies of the Shadowfell, and many have spent a significant portion of time dwelling in that lightless place.  Many Shadows use their abilities to act as assassins, and some even come to revel in the act of murder.  But a powerful Shadow does not need the approval of civilization, as they can vanish before anyone can stop them from committing their atrocities.  One of the few exceptions to the evil Shadows are the Shadar-Kai, who are bound to the service of the Raven Queen.  These Shadows tended more towards neutrality, wandering the Material Plane to gather memories for their mistress and preparing the dying for their journey into the afterlife by forcing them to confront their fears and pains.  There were very few good Shadows; most who were good learned their techniques by studying and reverse engineering the Shadow Vials of an evil Shadow they defeated.  They used the powers of the Shadow to scout ahead and end combat encounters quickly to keep their allies safe.

Whereas many rogues depend on their agility and silver tongues to get them out of bad spots, most Shadows rely primarily upon their wits.  The smarter a Shadow is, the more powerful a Shadow Vial they will be able to create.

Shadow Form

Starting at third level when you choose this archetype, you can, as an action, smash an alchemical mixture known as a Shadow Vial on the ground at your feet.  Shadowy tendrils cover your body, making you seem to flit in and out of darkness.  This ability lets you appear lightly obscured even in bright light, heavily obscured in dim light, and completely invisible in darkness, even to other creatures with Darkvision.  The alchemical components in your Shadow Vials have enhanced your vision, giving you Darkvision of 60 feet for the duration.  Shadow Form gains additional enhancements depending on whether your chose proficiency with the Alchemist's Supplies or the Poisoner's Kit (detailed under Bonus Proficiencies).

 Upon finishing a long rest, you can create a number of Shadow Vials equal to your Intelligence modifier.

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain expertise with stealth, and you can choose to be proficient with either the Alchemist's Supplies or the Poisoner's Kit, which modify your Shadow Vials in different ways.

Alchemist's Supplies

You gain proficiency with the Alchemist's Supplies, allowing you to create intensifying alchemical concoctions that benefit your Shadow Vials.  At level three, you gain a +2 to AC while using Shadow Form and, when using the Hide action in at least half cover, you can make the Stealth check with advantage.  At level nine, you can attempt to Hide in plain sight.  You must make a DC 20 Stealth check with disadvantage.  On success, you are considered hidden.  You must again make a DC 20 stealth check with disadvantage for every ten feet you move, but you do not provoke opportunity attacks as long as you continue to succeed on your Stealth checks.  If you attack while hidden, you gain advantage on your attack rolls as normal and are no longer hidden. Your roll automatically fails against creatures with Blindsight, Truesight, or Tremorsense.  At level thirteen, you no longer have disadvantage on your Stealth skill check to Hide in plain sight or when moving while hidden.  At level 17, you can cast Invisibility on yourself once per use of a Shadow Vial.

Remember, as a rogue, you can use your Cunning Action to take the Hide action as a bonus action.

Poisoner's Kit

You gain proficiency with the Poisoner's Kit, allowing you to create deadly poisons that coat your weapons while making sneak attacks.  The more intelligent you are, the more potent your poison is.  While using Shadow Form after having chosen proficiency with the Poisoner's Kit, you now make a Toxic Ambush instead of a regular Sneak Attack.  You still do the base Sneak Attack damage listed in the Rogue Table, but you now also do poison damage equal to 1d4+your intelligence modifier.  In addition, the target must succeed on a Constitution check equal to 8+your proficiency modifier+your intelligence modifier or be Poisoned.  The damage increases to 1d8 at level 9, 1d12 at level 13, and 2d8 at level 17.

Decoy

Starting at level nine, when you smash a Shadow Vial, you create an Illusory Decoy, similar to the Mirror Image spell.  You only create one decoy, but if an enemy targets you and hits, they must target your decoy unless they make an attack roll that exceeds your AC by 5 or they make a critical hit.  The decoy has a number of hit points equal to you Intelligence score.  When the hit points are reduced to 0, the decoy explodes, dealing 4d8 force damage in a five-foot radius.

Shadow Striking

Beginning at level 13, you can focus more on striking when you are ignored.  The Shadow can do the most damage when no one is paying attention to them.  When you have not been the target of an attack or been forced to make a saving throw for at least one round and are under the effect of one your Shadow Vials, you gain +3 to all melee and ranged attack rolls.  This does not apply for the first round of combat.  You can also make a critical hit on a 19 or 20.

Your constant use of the Shadow Vials have increased your other senses as well as your vision.  You gain expertise with Perception.  You now have Blindsight at a range of 30 feet.  You cannot be surprised by attacks originating within this radius.  Invisible creatures no longer have advantage on their attacks against you, and you have advantage on all Perception checks to find hidden creatures.

Pandemonium

Beginning at 17th level, when you smash a Shadow Vial, you release a cloud of hallucinatory gas.  This gas creates an effect similar to a level 6 Confusion spell.  All creatures with twenty feet must make a Wisdom saving throw of 8+your proficiency modifier+your intelligence modifier or be Confused.  Upon being Confused, the creature takes 1d10 psychic damage and must roll a d10 at the beginning of each turn. The creature is subjected to the following effects:

d10	Behavior
1-3	The creature becomes frightened of you, and must spend its movement trying to move as far away from you as it can, and it can’t willingly move to a space within 30 feet of you. It will not move into an obviously dangerous area, such as lava or a deep pit.  It cannot take reactions. For its action, it can use only the Dash action or try to escape from an effect that prevents it from moving. If there’s nowhere to move, the creature can use the Dodge action.
4-6	The creature suffers from terrifying hallucinations.  It drops prone and shields its eyes from your "terrifying" visage.  Until the start of is next turn, it is considered blinded and incapacitated.
7-9	The creature makes a melee attack against its nearest ally.  If there are no allies within its range, it uses all its movement speed to get as close to an ally as possible.
10	The creature doesn't move or take actions this turn.  It can still use its reaction to make opportunity attacks.

 

You are immune to the effects of Pandemonium, but your allies are not.  The gas dissipates after a few seconds of smashing a Shadow Vial, so Pandemonium can only effect creatures that start their turn in the radius of Pandemonium or move into the radius of Pandemonium until the start of your next turn. A confused creature is subjected to the effects of Pandemonium for 1 minute, regardless of whether or not they move out of the original radius.  Confused creatures can attempt to make the saving throw again at the beginning of their turn.  On success, the effect ends.  On failure, they take another 1d10 psychic damage and must reroll on the Pandemonium table.