The Grayshrouds

When you need something stolen, or a message sent you contact one of the Grayshrouds, and they’ll set something up. The criminal underbelly of Portabria and Mistyvale are connected by networks of informants and spies, allowing for swift capitalization on any gap in the law. Famous for their discretion Grayshrouds come from nearly all walks of life, from grifters and conmen to demolitionists or thieves. Most of them spend months without contact from their fellows, except when someone is interested in hiring some ‘extra muscle’. The middleman takes a cut, but the system has genuinely made it more lucrative for criminals in northern Lumora.

Members value discretion above all else, and as such often wear masks, scarves, or even their titular shrouds to conceal their faces when on the job. Attempting to unmask a member or follow them home is considered enough of a violation to get you blacklisted for the mere attempt. Beyond that, nearly everything else is left up to the individual member, some require specific payments or a riddle be solved, others working on a whim or only jobs that pique some sort of interest.

No one really knows who set up the original system, and even fewer actually care. So long as jobs keep coming in and the law remains fallible there will always be criminals.

Rules
Unmasking another member or attempting to discern their identity is a violation of rules and is punished by blacklisting and a bounty being placed on you.

Speaking of your identity as a Grayshroud or meetup locations is a violation and is punished by blacklisting.

The Conspirators
You gain a Coin of Contact (Detailed in Homebrew Content), allowing you to identify fellow Grayshrouds while on a job. Characters with proficiency in Intelligence (History) can recognize the coin by succeeding on a DC 18 Intelligence (History) check. This outs you to them as a Grayshroud and opens you to PvP with players on that session. Travel costs are negated and you gain double fame for all  sessions, and sessions taking place in Contested Territory.

Tricks of the Trade
Grayshrouds operate within a criminal organization, and specialization is valued over generalization in the eyes of those who make plans. You’ve begun to cultivate a useful role for your work on the team. You learn to speak the secret code of Thieves' Cant and choose one of the listed abilities to gain;


 * Lookout: You’ve sharpened your senses enough to pinpoint creatures even through walls and doors. While moving at less than half your speed, you can use the Search action to identify the locations of any creature within 30 ft of you, allowing you to ‘perceive’ creatures through walls. You must beat the Stealth check of any creature attempting to hide from your senses as normal.
 * Demolition Man: Bombs, grenades, guns, sledgehammers, and rams. The tools of destruction have always fascinated you. Attacks against unattended objects, such as doors, walls, locks and safes cannot miss, and treat all dice rolled as if they had rolled the maximum.
 * Smooth Operator: Your charisma is legendary, when you succeed on a deception check against a creature, you charm the creature for the next 24 hours. This charm ends if you make an attack in the presence of a charmed creature. Additionally you can quickly fabricate an identity from whole cloth, so long as you look as though you belong, most creatures will not question simple explanations as to your presence.
 * Bouncer: You’ve always been a thug, and the intimidating demeanor you project can help turn away eyes and ears from your activities. When you succeed at an intimidation check, creatures will not question your presence or activities for 24 hours, allowing you to shuffle people away from a site of a crime, or strong arm people into opening doors for you and your allies.
 * Cleaner: Crime is dirty business, and none is dirtier than covering up a crime. In a world with magic that can spot a criminal miles away, sometimes you need someone capable of erasing the passing of others. You know a few tricks, and can use an action to become undetectable by magic for one minute. While undetectable, you cannot be detected through detect thoughts, scrying, or other methods of detecting you. Additionally while undetectable magical traps and similar effects such as runes do not trigger from your passing.
 * Infiltrator: You have a climb speed equal to your speed, but lose this climb speed at the end of any consecutive turn you spend climbing, regaining it only when you spend at least one turn without climbing, or jump from one surface to another. When you succeed at unlocking a door or other portal using thieves' tools, you gain advantage on Stealth checks for ten minutes, as the adrenaline rush of a smooth entry enhances your perception and reaction time.
 * Mastermind: You’re an expert at planning, with an eye to become one of the brains behind the extensive operations of the Grayshrouds. You often try to take the lead on jobs, and are able to use the Help action, or the Bardic Inspiration class feature if you possess it to assist any creature that can hear you, regardless of distance.

Secondary Role
Choose an additional Trick of the Trade to learn.

Know a Guy
In the underworld, it helps to have allies and people who’ve got your back. Choose two of the following contacts to have. You know someone in many of the major cities of Lumora who can provide the listed service to you at a fair and trustworthy cost.


 * Fence: A reliable place to sell off stolen goods can help find the best payout for your work. Increase the rewards from ‘Job’ sessions and the worth of stolen goods by 10%
 * Forger: Masterful recreations can be used both as decoys and infiltration methods. So long as you can provide reasonable access, images, or your request is easy enough, your contacts can have a relatively reliable forgery made within a day or two.
 * Alchemist: Many cities keep a close eye on explosives, poisons and other temporary tools used in Grayshroud crimes. Access to an alchemist means you’ll always have a source of whatever consumables you might need, though this isn’t a guarantee that such purchases will come cheap.
 * Bookie: Many Grayshrouds like to dip their fingers in the betting rings within cities. Bookies can provide additional cash flow to the Grayshroud low on funds. You may make downtime criminal actions with advantage, and may increase the reward for any ‘Job’ sessions you do by 20% by tipping a bookie off to start a betting pool about your planned heist. Though this does have a chance of making your life harder when word of your planned crime gets to those with the power to stop it.
 * City Official: Sometimes you need obscure documents or legal assistance. Worst case scenario, an official on your side might make a stint in prison shorter or escape easier. If a job goes wrong you can reliably bribe your way out of any prison sentence, though obviously how much you’ll need to fork over will vary based on the severity of your crimes.
 * Watchman: The city watch is your enemy, but an eye on the force can tip you off to some of the plans of your enemies, maybe get a blind eye turned to some of your crimes, or even just delay the response time of the watch to a crime in progress.
 * Architect: Sometimes all you need is a map. Architects can provide you with a reliable plan of any building in the city, so long as it’s on the books, allowing you to coordinate with your team better.
 * Dilettante: Rich folks have access to places where the lower classes don’t. Having one willing to vouch for you can help your plan to infiltrate or access certain locations. Where relevant, you gain advantage on social rolls regarding maintaining a cover identity or finding things out where your vapid socialite friend can help you out.
 * Bagman: Escaping with a target or other loot can be difficult, and having to run across the city with lots of money can be annoying or even lethal. Hiring a reliable bagman will allow you to drop your ill-gotten gains off somewhere nearby to be collected later, or brought to you after you’ve made your escape.
 * Insider: You sometimes feel like you’ve met half the people on Lumora in various bars or recreational establishments. Most jobs you can find someone you know who works closely with your target. The extent and price of their help, however? Who can say.

Enhanced Tricks
You become more comfortable in one of your chosen roles, gaining an additional ability for one of the Tricks of the Trade you already possess:


 * Lookout: You can use the Search action as a bonus action. You can use your reaction to allow an ally that can hear you to move up to 15 ft, or to move 15 ft yourself.
 * Demolition Man: You’ve become a master of working with explosives and alchemical items. You can take an action to change the properties of a mundane consumable item, though only one adjustment may be applied at a time.
 * You may increase the radius of the item by 5 ft
 * You may decrease the radius of the item by 5 ft, and halve the distance the item can be heard going off.
 * You may change the shape of an item from a radius to a cone with the same distance.
 * You may double the damage an item deals by reducing the affected area to a 5 ft square.
 * Smooth Operator: Knowing how to roll with a lie or turn a faux-pas into an amusing anecdote can go a long way to getting you in with the target. When you fail a social roll, such as Insight, Deception, Persuasion, or Intimidation, you can make a different social check as a reaction, success on this alternate roll brings all the same benefits as if you had succeeded on the first check, and prevents any negative consequences from your first check. Once you have used this feature on a given skill check, you cannot use it again on that check until you have completed a short or long rest.
 * Bouncer: Sometimes a job requires you to crack some skulls. You feel right at home doing so, and have learned how to modify your tougher armors to sneak in, allowing you to bring a bit more protection on your jobs. You do not have disadvantage on Stealth checks based on the armor you’re wearing, and you gain proficiency and mastery in medium and heavy armor.
 * Cleaner: Grayshrouds try and avoid killing whenever they can. The heat from such a thing can bring down retribution from the watch like a hammer. Sometimes, though, death is unavoidable. The best a cleaner can do is make sure a kill isn’t discovered till the shrouds are long gone. You can hide bodies in spaces normally too small, snapping bone and rearranging limbs to make things fit. You can hide bodies and other objects in containers up to two sizes too small for them.
 * Infiltrator: You gain the Skulker feat, if you already have it, you gain a bonus feat.
 * Mastermind: Sit at the center of your spider’s web, pulling the strings to engineer success. You can use the Help action as a bonus action on your turn, and you may use your reaction to allow a creature that can hear you to reroll a check or save they’ve made.

Calling Favors
The Shrouds have hands everywhere, though calling upon them is a task not taken lightly. As a bonus action on your turn, you can tell your Game Master you are Calling in a Favor. One NPC in the scene is revealed to be a double agent, or, barring that, appears from a nearby hiding spot or other entrance, and comes to your assistance. Calling a favor like this immediately burns whatever identity the agent had when you called for the favor, and you must help them escape successfully. Using this power outs you as a Grayshroud to anyone who can see you, and failing to help in the escape of the agent you called on is considered a great failure as a shroud.

Master of the Craft
Choose and gain another Trick of the Trade, Know a Guy, and Enhanced Tricks ability.