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Prerequisite: Requires criminal background
 

Feature — Underworld Contacts (1/Long Rest)

 

You’ve done favors, broken promises, and buried secrets across the criminal world — and sometimes, those connections still pay off. Once per long rest, you can declare that you “know a guy” in or near your current region who operates in the underworld.

 

Describe who they are, how you know them, and what you’re asking for — a place to hide, contraband, forged papers, or inside information.

 

The DM then determines:

If your contact is available and within reach,

How their relationship with you stands (friendly, wary, indebted, hostile, etc.)

Whether they can or will help.

Depending on the nature of your request, you may need to make a Charisma (Deception, Intimidation, or Persuasion) check.

 

Favor Difficulty Table

Minor (DC 10): 

Shelter for the night, local gossip, stolen rations

Moderate (DC 15):

Smuggled goods, a forged pass, location of a mark

Major (DC 20):

Help escaping capture, assassination, or smuggling across borders

 

  

 

 

On a failed check, your contact still exists — but things go sideways. They might demand payment, attract unwanted attention, or double-cross you.

 

d6: Criminal Contacts You “Know”

 

d6

Contact

Description & Quirk

1

Rook the Fence

A jittery black-market trader who deals in relics and rumors. Hates being touched, but owes you for saving his neck from a bad deal.

2

Sable the Forger

Elegant and unbothered, she can fake anything from royal seals to holy scripture — for a price. Collects genuine signatures as trophies.

3

Marrik the Knife

A courier who moves messages and contraband through the city’s veins. Discreet, loyal, and always running from someone. Keep your secrets close — mostly because he’s tied up in them too.

4

Mother Greel

An elderly apothecary who brews poisons “for medicinal purposes.” Sees herself as the moral compass of the local thieves.

5

The Whisper Twins

Identical siblings who finish each other’s sentences — one’s a pickpocket, the other’s a snitch. They only meet you in crowded taverns.

6

Captain Varrin

Smuggler with a half-burned ship and a debt to nearly everyone. If he helps you, expect a favor owed in return — and fast.




When Things Go Wrong

When the contact can’t (or won’t) help, roll or choose from the table below to determine what complication arises.

d6

Complication

Description

1

The Heat’s On

Your contact’s under surveillance or being hunted by the guard. Meeting them puts you both at risk — or draws unwanted attention.

2

You Owe Me Now

They’ll do the job, but they demand a hefty favor, payment, or secret in return. Refuse, and word might spread that you don’t keep your promises

3

Crossed Wires

Someone else got to them first — your contact’s already working for a rival, bounty hunter, or law enforcer. Their help comes at a steep moral cost.

4

Set-Up

Your contact double-crosses you, willingly or under duress. Maybe they were paid off, maybe they’re scared — either way, it’s a trap.

5

Burned Bridge

They’ve been caught, retired, or turned honest. They can’t help you anymore — but they drop a name or clue that points you to someone new.

6

Collateral Damage

The job gets done, but something goes wrong — a fight breaks out, someone important gets hurt, or the evidence leads right back to you.

 

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