Source: Curse of Strahd: Optional Backgrounds

You are an informant for the Tears of Virulence who now lord over Phlan, but are also a double agent for the original town guard of Phlan, the Black Fist. For the Tears you’ve been tasked with ferreting out the secrets of Phlan's criminal underworld, insurgency, and the common peoples of Phlan. In exchange for reporting on the activities of dissenters, criminals, and other rebel elements, the Tears of Virulence leave you alone to conduct your affairs in peace.

In reality you work for the deposed Black Fists, sharing misinformation with the Tears of Virulence that often helps the Black Fists and other Phlan insurgents.

Since the evacuation of Phlan, you are even busier today than you ever were previously, as the number of dissenters among the refugees grows daily, while you are afforded many opportunities to spy on the peoples of Mulmaster and Elventree, to the pleasure of your contact(s) within the Tears of Virulence.

Skill Proficiencies: Deception, Insight
Tool Proficiencies: Disguise Kit, and one type of artisan’s tools or gaming set
Equipment: Disguise KitValue:25gp Weight:3lbs, common clothesValue:5sp Weight:3lbs, a Tears of Virulence emblem, a writ of free agency signed by the Lord Regent, a set of artisan’s tools or gaming set you are proficient with, and a pouchValue:5sp Weight:1lb with 15gp (payment for services rendered).

Feature: Double Agent

You have a reliable and trusty contact within the Tears of Virulence garrison in Phlan to whom you pass information and secrets. In exchange, you can get away with minor criminal offenses within the town of Phlan. In addition, your Black Fist contacts can help you secure an audience with the Lord Regent, the Lord Sage, members of the Black Fist, or deposed nobles and authority figures who are sympathetic to the Phlan refugees and insurgents.

[Note: This feature is a variant of the Noble feature.]

Double Agent Personality Traits

d8 Personality Trait
1 People are only as trustworthy as you are valuable to them. Always strive to be the most valuable person around.
2 My eloquence and sophistication are tools I use to avoid arousing suspicion myself.
3 I am a thrill-seeker, excited by covert and dangerous missions.
4 I live by my wits and always check every lock twice, just to be certain.
5 I never admit to my mistakes lest they be used against me.
6 I take every effort to be unnoticeable and blend into the crowd. Passersby rarely give me a second look.
7 I am prepared for any eventuality; including the day my usefulness as a spy comes to an end.
8 I always make certain to know my enemy before acting, lest I bite off more than I can chew.

Double Agent Ideals

d6 Ideal
1 Suspicious. In my experience, everybody has something to hide, and what they hide can usually hurt me. (Any)
2 Secretive. I trade in secrets, and am not about to let any of mine slip. (Any)
3 Hedonist. Life is short. I live my life to the fullest, as I know any day could be my last. (Chaotic)
4 Selfless. I use my position to help the downtrodden avoid persecution from the authorities. (Good)
5 Patriotic. I am a loyal supporter of Phlan and its leaders, and see my role as a solemn duty and necessary evil to prevent anarchy. (Lawful)
6 Manipulative. I use my knowledge to blackmail and manipulate others to my own benefit. (Evil)

Double Agent Bonds

d6 Bond
1 I was framed for a crime I did not commit, and seek to bring the true culprit to justice.
2 I am a part of an underground network that smuggles innocent civilians out of the city prior to being raided by the authorities.
3 I miss the glory days of Phlan, before the coming of the dragon.
4 I seek to prove myself worthy of joining the Black Fist as a member of their order.
5 My sibling was killed by a Tear of Virulence, and now I feed them false information whenever possible.
6 My family was wrongly imprisoned, and I act as an informant in order to secure their release.

Double Agent Flaws

d6 Flaw
1 I think too highly of myself, and have an exaggerated sense of self-importance.
2 I have difficulty trusting strangers. I see spies and informants everywhere.
3 Years of getting away with minor crimes has left me believing that I am above the law, and have diplomatic immunity above my station.
4 Years of seeing innocent people suffer have left me despondent and pessimistic for the future.
5 My desire for vengeance often gets me into trouble.
6 I am a spendthrift, and share my wealth with the patrons of my favorite tavern.