Conspirator

A master of plots and schemes, the artful Conspirator is a sharp-witted agent of disruption, able to concoct the most complex of ploys and enact great machinations. 

Many of this archetype define themselves by a profession or life's pursuit - the cunning Conspirator may be a deviant who works from the shadows to empower a faction, the affable face of a criminal outfit, a rebel who works in the open to rout out corruption, or a cult leader stringing along a band of naïve followers.

Devise Machinations

Starting when you choose this archetype at 3rd level, you learn how to concoct and execute complex schemes called Machinations.

Machinations Known. You know four Machinations, and learn two more when you reach 6th, 9th, 13th, and 17th level in this class. Whenever you gain a level in this class, you can choose to replace one of your known Machinations with a new one.

Enact Machinations. You can enact one of your known Machinations a number of times equal to your proficiency bonus, and regain any expended uses of this feature when you finish a long rest. When enacting a Machination, you gain and/or may use its listed benefits until the end of your next long rest.

Replicating Spell Effects. Some of your Machinations allow you to replicate the effects of spells. When replicating a spell effect, you must still provide any material components that would be required to cast the spell, and must concentrate on the spell if it requires concentration. Charisma is your spellcasting ability for these effects.

Saving Throws. Some of your Machinations require creature to make a saving throw. The saving throw DC for your Machinations is calculated as follows: Your Machination save DC = 8 + your proficiency bonus + your Charisma modifier.

Aid and Abet

You can administer and consume potions as a bonus action.

Anticipate Assault

When initiative is rolled, you can force a creature you can see within 60 ft. to make a Charisma saving throw. On a failure, the target is Poisoned for the first round of combat.

Artful Entrance

immediately after you make an attack against a creature that couldn't see you, you may make an additional attack as a bonus action. You may draw, stow, and reload a weapon as part of this bonus action.

Cloak and Dagger

When you roll initiative, you become Invisible until the first round of combat ends, or until you make an attack or cast a spell.

Collude

Prerequisite: 6th Level 

When an allied creature within 30 ft. of you rolls for an ability check in which you have Expertise, your ally gains a bonus to the check equal to half your proficiency bonus (rounding up).

Conspirator's Truncheon

Weapons that deal Bludgeoning damage are considered to have the Finesse property while you wield them.

Contact Cabal

Prerequisite: 6th Level

You establish a link with a covert network that can further your plots and schemes. When you select this Machination, choose a spell from the Warlock spell list with a casting time of 1 Action, and of a level equal to or lower than your proficiency bonus. You can replicate the effects of that spell as an action once before your next long rest.

Craft Conspiracy

Prerequisite: 6th Level

After spending an hour of focused conversation with a humanoid, you may force them to make a Wisdom saving throw. If they fail, choose an ideal - they adopt that ideal, and may remake the saving throw after 24 hours have passed. The effect ends on a success, and is permanently adopted after three consecutive failures.

You can also choose to change the ideals of a community. After completing a long rest in a community, you may craft a rumor and roll a d100. The rumor passes through the lips of a number of people equal to the roll. If you sue this Machination on a community for 30 consecutive days, make a Charisma (Deception) check contested against the community's Wisdom (Insight) check, using a Wisdom modifier deemed appropriate by the DM. If you succeed, choose an ideal for the community to permanently adopt.

Foil Ruse

Prerequisite: 6th Level

You cannot be Surprised. You can cause a creature that is Surprised within 5 ft. of you to act normally using a bonus action.

Foul Whisper

As a bonus action, you can replicate the effects of the Command spell at a level equal to or lower than your proficiency bonus. Once you use this ability, you cannot use it again until you finish a short rest.

Hand in Glove

Prerequisite: 6th Level

On your turn, you can use a bonus action to mark a creature within 30 ft. of you.

After one of your allies hits the creature with an attack before your next turn, you can use your reaction to roll your Sneak Attack dice and deal damage equal to the total. The target must be within 15 ft. of you to use this reaction, and the damage is the same as the attack that triggered the reaction. Once you use this reaction, you must finish a short rest before you can do so again.

Impeccable Forgery

As an action, you can select a spell from the Wizard spell list with a casting time of 1 Action, and a level equal to or lower than your proficiency bonus before attempting to replicate its effects.

Make a Charisma check using your Forgery Kit, with a DC equal to 15 + the spell's level. On a success, you replicate the effects of the spell. Once you successfully replicate the effects of a spell with this Machination, you cannot do so again until you select this machination again at the end of a long rest.

Imperious Orders

Prerequisite: 13th Level

Once before the end of your next long rest, you can use a bonus action to replicate the effects of the Mass Suggestion spell at a level equal to or lower than half your Rogue Level, up to 9th level.

Ingenious Exchange

You can access the inventory of any willing creature within 100 ft. of you, as if it were your own inventory.

Long Con

Prerequisite: 13th Level

When an instance of combat begins, and you aren't surprised, Incapacitated, or Unconscious, you can use your reaction to draw you weapon, move up to half your speed, and take an action granted to you by your Cunning Action.

Occult Misappropriation

When you roll dice for your Sneak Attack, you can choose to expend and roll a hit die. When you do, you add the result to the total damage of your Sneak Attack, and change the damage type of your Sneak Attack to Necrotic damage.

Prognostication

You add your Proficiency bonus to your initiative rolls.

Prudent Measures

When you would take your turn in combat, you can choose to delay your turn for the round, and act on initiative count 1.

Reproach

As an action, you can choose a humanoid creature within 5 ft. of you that is no more than one size category larger than you, and attempt to bind it to your words.

Make a Charisma (Intimidation) check contested by the target's Wisdom (Insight) or Charisma (Persuasion) check. If you succeed, the target is Grappled. A grappled creature can use its action to escape - to do so, it must succeed on a Wisdom (Insight) or Charisma (Persuasion) check contested by your Charisma (Intimidation) check. The grapple otherwise ends if you are ever more than 5 ft. away from the creature, are unable to speak, or if you choose to use it.

Rule by Force

Your fists are considered to be simple melee weapons with the Finesse property, and deal 1d6 bludgeoning damage on a hit.

Studious Groundwork

You may read and cast spells from Spell Scrolls that contain spells from the Wizard spell list. You are considered to be able to cast spells of a level equal to your Proficiency bonus for the purposes of determining whether you must make an ability check to cast the spell. Charisma is your spellcasting ability for these spells.

Subterfuge

You have advantage on Charisma (Deception) checks.

Surreptitious Supplies

Once before the end of your next long rest, you may use an action to conjure a non-magical item of a gold cost equal to up to ten times your Rogue level. At the end of your next long rest, the item or what remains of it vanishes.

Two-Part Plan

Prerequisite: 9th Level

When you Ready an action, you may make an attack with a melee weapon as part of the same action.

Vitriol

Prerequisite: 9th Level

Once per turn, you can add a bonus to one of your damage rolls equal to your Charisma Modifier.

Weave The Mind

When you move while you are considered to be Hidden from one or more creatures, you remain hidden from them, even while moving through their line of sight. If you break-up or stop your movement while in a creature's line of sight, this benefit immediately ends.

When A Plan Comes Together

When an allied creature makes a melee attack against a creature within 5 ft. of you, you can use your reaction to make an attack against the same creature.

Whispered Heresy

You can replicate the effects of the Vicious Mockery Cantrip as an action. If your target qualifies for your Sneak Attack, you can add your Sneak Attack damage to the spell's effect.

Dubious Prestige

Also at 3rd level, you gain proficiency in the Deception skill and proficiency with Forgery Kits. 

Back Alley Dealmaker

At 9th level, you gain proficiency in Charisma saving throws.

Abrupt Contrivance

Starting at 13th level, you know how to make the best out of an abrupt situation.

Before you roll initiative, you can choose a known Machination that you aren't presently enacting - you can enact that Machination until the end of combat.

Seen to Fruition

At 17th level, your planning is beyond refute, and failure is simply part of one of your schemes. 

The first time each round that you miss an attack or fail a saving throw, you gain Advantage on the next attack or saving throw you make before the end of your next turn.