CREDITS

Designer: John Bacovcin

Editor: John Bacovcin
Art Director: John Bacovcin
Template: Simple Microsoft Word Template by Laura
Hirsbrunner
Cover Illustrator: John Bacovcin via https://www.canva.com/
Special Thanks: To the RPG Writer Workshop for giving me the
framework and confidence to achieve my dream of putting my
adventures to paper. Check out their website here
https://www.rpgwriterworkshop.com/.
Playtesters: Ryan Siebring, Courtney Schulze, Daniel Geerdes,
Trevor Worth, and Randy Lemons.

ON THE COVER
A morose woman in a mask looks forward knowing what
needs to be done.

Disclaimer:

DUNGEONS & DRAGONS, D&D, Wizards of the Coast, Forgotten Realms, the dragon ampersand, Player’s
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This work contains material that is copyright Wizards of the Coast and/or other authors. Such material is
used with permission under the Community Content Agreement for Dungeon Masters Guild.

All other original material in this work is copyright 2020 by Jonathon Joseph Bacovcin and published
under the Community Content Agreement for Dungeon Masters Guild.

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1
TABLE OF CONTENTS
Credits ................................................................................ 1
Table of Contents............................................................... 2
Introduction ....................................................................... 3
Story Overview ........................................................................... 3
The Villain ................................................................................... 3
Adventure Structure ................................................................. 3
Chapter 1:............................................................................ 4
Shadows Lengthen ............................................................ 4
The Revelation ...........................................................................4
Adventuring Hooks: ..................................................................4
Self-Preservation ............................................................... 4
Do it for the Prestige ...........................................................5
Doing your Civic Duty .........................................................7
Locations of Field Ward ........................................................... 7
The Slaughterer’s Skull ......................................................7
Sorrow’s Respite ................................................................. 8
The End Shift Tavern ......................................................... 9
The Northern Watch Barracks ........................................ 10
Square Market Alley .......................................................... 10
Chapter 2: .......................................................................... 11
Encroaching Darkness ..................................................... 11
The Revelation: ......................................................................... 11
Additional Surveillance .................................................... 11
Surveilling Gweniver......................................................... 11
Surveilling the Captain ..................................................... 11
Chapter 3: ......................................................................... 12
The Shadow Witch ........................................................... 12
The Revelation: ........................................................................ 12
The infiltration ........................................................................ 12
Daytime Infiltration .......................................................... 12
Nighttime Infiltration ...................................................... 12
The Confrontation................................................................... 12
What your doing is wrong ................................................ 12
Kill the Witch ...................................................................... 13
Kill the Guards .................................................................... 13
Persuasion Boss Battle Rules .......................................... 13
Conclusion: ...................................................................... 13
If the party helped Gweniver escape without killing
Captain Kepesh ................................................................... 13
If the party killed Gweniver ............................................. 14
If the party killed Captain Kepesh .................................. 14
Rewards ..................................................................................... 14
Appendix A: ...................................................................... 15
Gweniver Wildheart’s Backstory ......................................... 15
Appendix B: ...................................................................... 16
Gweniver Wildheart ..........................................................16
Shadow Wretch ..................................................................16
Captain Kepesh ................................................................... 17
Appendix C: ...................................................................... 17
Appendix D: ...................................................................... 18
Map of Field Ward Neighborhood........................................ 18

2
INTRODUCTION When the tattoo is broken the bearer will
transform into a monster of shadow and

STORY OVERVIEW
undeath called a Shadow Wretch. Combat
statistics for both Gweniver and her creations
Feel free to paraphrase or read the following can be found in Appendix B. When the party
text out loud to your players when you start: first meets her unless they are directed to her
through the course of their investigation, she
should seem kind and be generally helpful to
try and throw her off her scent. She will only
get directly antagonistic if confronted or if
she learns that the party is working with the
City watch. Depending on the party there is a
chance for them to switch sides and aid
Gweniver in her quest of revenge. If that
happens be prepared for a lot of chase scenes
and infiltration as they will be trying to
assassinate a City watch Captain.

ADVENTURE STRUCTURE
Hearts of Shadow is a murder mystery
revenge plot split into three chapters:
Shadows Lengthen, where the party will start
out on their investigation and encounter the
villain and her monsters, Encroaching
Darkness, were the party’s suspicions are
Hearts of Shadow is an adventure designed fully aroused and they closely watch the
for a party of four to six, levels 3-5. This villain, and finally The Shadow Witch were
adventure has a decent mix of combat, the party confronts the villain and the
investigation, and social interaction so all adventure is resolved. Each chapter will start
character classes will prove useful to the with a revelation that the party should come
party. It can be done as a standalone one-shot to before they move on to the next section of
adventure or incorporated into Waterdeep: the adventure. There are multiple ways to get
Dragonheist as additional content or as an to these revelations, but do not be afraid to ad
adventure that can be played if not everyone lib or mix paths if the party does the
can make it. unexpected. After all no plan survives first

THE VILLAIN contact with the party! Listed below are brief
descriptions of adventure hooks you can use
The main antagonist of this story is a halfling
to get the party interested in the adventure.
wizard named Gweniver Wildheart, her
Occasionally you will find text boxes like the
backstory can be found in Appendix A for
one below. These are descriptions that can be
more insight into her character and her fall
read aloud to your players or summarized
from grace. She owns and operates a small
with your own flair. Feel free to embellish on
charms and protection shop in Field Ward to
what is provided based off what your players
find victims and to serve as a cover for her
are doing and saying.
actions. She is the one responsible for the
kidnappings and for the monsters roaming
the alleys at night. To do this she is using
enchanted crystal charms and henna-like
tattoos. The orange charms she sells in her
shop contain powerful enchantment magic
that she can activate to make people obey her
orders via enhanced versions of the charm
person and command spells. Her tattoos are
the result of years of magical research and a
pack with an evil entity of the Shadowfell.

3
CHAPTER 1: address the party. In a rather gruff and
gravelly voice he will say:

SHADOWS LENGTHEN
THE REVELATION
The party should end this chapter with
suspicions about Gweniver and that the
Shadow Wretches are a serious threat.

ADVENTURING HOOKS:
Listed below are the three main adventuring
hooks that you can use to entice the players
into starting their adventures. In “Self-
Preservation” the adventurers will be spurred
to stop these monsters due to them either
living in Field Ward or having some
connection to it. In “Do it for the Prestige”
the adventurers will be recruited by one of
three guilds the Zhentarim, the Harpers, or
the Order of the Gauntlet. In “Doing Your
Civic Duty” the party is attacked by one of the
Shadow Wretches early on and the City Watch
saves them. In recompense they ask the party
to help them get to the bottom of what is
going on.

SELF-PRESERVATION

If the party agrees then Valdric is overjoyed

and calls over Mary, one of his barmaids, to
get the party some more drinks and to answer
any questions they might have. Mary has an
intricate tattoo on her forearm and a blue
crystal charm around her neck. Both are from
Gweniver’s shop and Mary will tell them that
they are for warding off evil and for
guaranteeing good luck. She recommends
they go and see Gweniver at her shop the
The party will start out in the Slaughterer’s Sorrow’s Respite to get some charms of their
Skull tavern a run-down tavern that while own if they are going to stay out overnight.
large barley seems to be pulling in enough
money to survive. The owner Valdric, known
around town as Valdric the Ugly, is an aging
half-orc man who has seen his fair share of
scraps. Cuts and scars litter his skin, his nose
is set at an awkward angle, and one ear is
missing replaced by a slightly rusty tin horn.
Valdric will brighten when he sees the
adventurers approach and will insist that they
find an empty table and that he will be there
shortly to chat with them. After pouring a few
more rounds he comes over to the table to

4
DO IT FOR THE PRESTIGE much of his life grifting and hustling the
If none of the party decide to have any people of Waterdeep. It was only when he was
connection to Field Ward and they have some offered legitimacy with the Black Network
connection to some of the guilds within that his combat and subterfuge really took
Waterdeep this may be the best hook to use. off. He is a smooth talker who is always
Depending on which of the two guilds the pleasant and is slow to anger. If the party
adventurers have earned some renown with fights him or you want to let them recruit
choose which NPC to have them meet in the him, he uses the Spy statistics found on page
Slaughterer’s Skull. Listed below are the two 349 of the Monster Manual. As the party
guilds, their associated quest giver, and their enters the tavern Lucky will stand and wave
introductions. All these hooks start with the them over.
party receiving a mysterious letter asking
them to come to the Slaughterer’s Skull in
Field Ward. What follows is a description of
the tavern.

As you approach the tavern mentioned in

the letter you received you are unsure to
even call it a tavern. The tavern itself is a
combination of several other shacks and
squat buildings cobbled together with
cracked bricks and roofed with broken clay
shingles. The interior is absolutely filthy as
the namesake suggests this tavern is the
favorite stop of the various trades people
who work in Field Ward, mainly butchers,
tanners, or anyone else who does a job
where a strong stomach and dull sense of
smell are an asset. Due to the clientele the
air within the tavern is foul smelling of
meat just starting to turn and harsh
chemicals. No music fills the tavern in the
traditional sense but the sounds of the near
constant bar brawl that roams from room
to room provides a background noise that is
distinctly Field Ward.

THE ZHENTARIM
The Zhentarim or Black Network is a large
organization of mercenaries and smugglers
whose members are willing to do anything if
the price is right. They seek to gain as much
power across the world as they can and are
willing to crush those who get in their way.
The quest giver for the Zhentarim is an up
and coming star for the Zhentarim in
Waterdeep. A blue skinned teifling named
Leucious “Lucky” Le’ Guy. Lucky has spent

5
After this initial introduction Lucky is willing
to share the following pieces of information
with the party.
• That some of his informants who live here in Field
Ward seem to have gone missing. The last time he
spoke with one of them was by the Square Market by
the North Gate.
• He has heard that during the night strange and terrible
monsters have now been roaming the alleys. From
what he has heard they seem to attack
indiscriminately.
• What few informants he still has have told him that
there is a young halfling woman who owns a shop that
has been selling charms and special tattoos that are
reported to ward off evil and guaranty good luck.

Once the party has finished their conversation

with Lucky he will bow and take his leave
reminding them that the Black Network has
ears everywhere and he will be here most
days for them to report their progress.

THE HARPERS
The Harpers are a loose collection of like-
minded individuals who oppose evil and
tyranny where they find it. Wherever their
cells operate they try and support equality
and fairness. Always acting in the shadows,
the Harpers seek to bring equality to the
world without anyone ever knowing that they
had a hand in it. The quest giver for the
Harpers is a new cell member here in
Waterdeep a half elf woman named Isabella
Strongfellow. Standing at average height her
rosy cheeks and strawberry blond hair make
her stand out in the Slaughterer’s Skull, but
that does not seem to dampen her cheery
disposition. Always looking for the best in
everyone she meets Mariana is the pinnacle of Once she is done explaining the job Isabella
upbeat positivity. If the party seeks to gain will also give out these three pieces of
her aid or attacks her use the Spy statistics on information.
page 349 of the Monster Manual. She will be
• Someone has been kidnapping beggars as they sleep.
waiting for the party outside the tavern and This does not seem to be an issue near a local shop the
waves them over to her as they approach. Sorrow’s Respite.
• The City Watch contingent that patrols the High Road
near here is very on edge. One of their patrols was
attacked last night near Square Market.
• The watch captain, Captain Kepesh, has been seen
patrolling the streets again, very unusual.

After the party finishes their conversation

with Isabella, she will thank them for helping
her out and encourage them to come back
anytime to keep her updated or just to talk.
Once she is done explaining the job Isabella
will also give out these three pieces of
information.

6
DOING YOUR CIVIC DUTY City Watch can be seen patrolling the streets
This hook is the most straightforward but and some even stray from the High Road
also the most dangerous. As the party is which is highly unusual. Each place will have
wandering the streets of Waterdeep have a description text box to read to the players
them be attacked by one Shadow Wretch, and have clues that can be found at that
statistics can be found in Appendix B. As the location. Bear in mind the party should bot
Wretch attacks read this description of the progress to the next chapter till they have met
creature. Gweniver or Captain Kepseh and have had at
least one combat encounter with the Shadow
Wretches.

THE SLAUGHTERER’S SKULL

The starting location for two of the plot
hooks. The Slaughterer’s Skull is a popular
hangout for the various butchers and tanners
who work in Field Ward. It is number 1 on the
map at the end of the adventure. If you used
the “Doing Your Civic Duty” plot hook than
read this description as the party approaches
and enters the tavern for the first time.

As you approach the tavern mentioned in

the letter you received you are unsure to
The Wretch that attacks the party is already even call it a tavern. The tavern itself is a
transformed. After it dies the shadows fade
combination of several other shacks and
away to reveal the broken and shredded body
of a human man. When searched the squat buildings cobbled together with
following pieces of information can be found: cracked bricks and roofed with broken clay
• There is a strange orange color crystal growth on the shingles. The interior is absolutely filthy as
creature’s chest.
• With a DC 15 investigation or perception check a tattoo the namesake suggests this tavern is the
of various arcane runes can be found on the tattered favorite stop of the various trades people
remains of the corpses forearm.
who work in Field Ward, mainly butchers,
Once the fight is over a gruff looking silver
tanners, or anyone else who does a job
dragonborn will approach them and ask them
about what just happened. He will then tell where a strong stomach and dull sense of
them that similar things have been attacking smell are an asset. Due to the clientele the
the members of his Watch contingent in Field
air within the tavern is foul smelling of
Ward and will ask the party to help him root
out the cause and destroy it. For their service meat just starting to turn and harsh
he is willing to offer 250 gold dragons. He will chemicals. No music fills the tavern in the
then tell them to meet him at the End Shift traditional sense but the sounds of the near
Tavern in Field Ward tomorrow morning to
constant bar brawl that roams from room
get started.
to room provides a background noise that is
distinctly Field Ward.
LOCATIONS OF FIELD WARD
The party can begin their investigation in
several places. As they visit and investigate, Valdric the bartender knows the following
they will encounter a frightened populous things and will gladly share them with the
that quickly goes about its business during party if they say they are working to solve the
the day and hurriedly returns home to locked problems plaguing Field Ward.
doors as night comes. A larger contingent of

7
• These attacks seem to be targeting the City Watch, dexterity check plus thieves’ tools proficiency
which is bad news for Field Ward.
if applicable or by a DC 18 strength check to
• Many of the Watch go to the End Shift Tavern when
they are done patrolling to relax. It may be a good break the wooden doors. Breaking the doors is
place to go to get a feel for the Watch’s attitude. incredibly loud and will draw the attention of
• Gweniver Wildheart’s shop Sorrow’s Respite has had a any people at the front of the shop and
large uptick in customers recently. They say her
anyone inside the shop. The people in line get
charms and mystic tattoos can repel evil and bring
good fortune. rather disgruntled if the party force their way
into the shop but will not start a conflict and
One of Valdric’s barmaids Mary is a hidden
will run if attacked. If the party approach the
member of the Xanathar thief guild and while
shop at night, there will be two people
she does not know it has been marked for
guarding the front door and one person
death by Gweniver. Her orange charm will
guarding the cellar door. All these people are
force her to transform and attack any City
wearing the orange crystals and have the
Watch person who enters the Slaughterer’s
tattoos that will transform them into Shadow
Skull. This is an opportunity to have the party
Wretches.
fight a Shadow Wretch in a more chaotic
environment. SORROW’S RESPITE INTERIOR
Read the following description the first time
SORROW’S RESPITE the party enters the shop.
Sorrow’s Respite is owned by Gweniver
Wildheart a stout halfling wizard/warlock
who has lived in Field Ward for some time. It The interior of the shop is softly lit with
is labeled as number two on the map. With all candles and blue and purple gems floating
the recent attacks and rumors her shop has in sconces placed around the walls. Deep
been seen as a safe haven from the darkness
blue curtains cover the windows and drape
and many citizens of Field Ward have begun
to congregate there in their off hours. As the across the counters and display cases. A
party approaches for the first time read. faint smoky fog lingers in the air. You can
see a few customers milling about the shop

Standing before you is a quaint two story with a small woman standing near a man

building with a wooden sign hanging from a lying face down on a table a large feathered

post depicting a raven sleeping on a grave. quill in her hand. The whole shop smells of

Near the steps of the store lie a small lavender and patchouli given off from the

candle lit shrine with a small portrait of a many censors that you see hanging from
the ceiling.
half-orc female in chain armor. A line of
people stretches out from the shop with As the party enters a small call can be hear
smaller groups loitering around and from a raven that roosts above the door. It
gossiping. They fall silent and turn to look flutters over to Gweniver and she will pop her
head up and tell the party that she will be
at your approach only for a moment before
with them in a moment. Once she has done
they go back to gossiping. tattooing her current customer she will hop
down and start conversing with the party. If
The portrait in the shrine depicts Jaisa, asked about the current goings on she will
Gweniver’s lost love who tried to clean up this reveal the following information, though a DC
section of Field Ward but was killed in a 20 insight check will reveal that she is
mugging several years ago. If asked any of the certainly hiding something and is not being
people milling around the shop will give this entirely truthful.
• People around Field Ward are terrified about the
information to the party. Around towards the
recent bouts of kidnapping and the monsters that have
back of the shop in the eastern alley there is a
been roaming the streets. Some are even saying that
cellar door made of wood and locked with they are connected as they started at the same time.
chains and a sturdy padlock. The lock itself • She has been trying her best to keep everyone calm no

can be picked with by beating a DC 15 thanks to the Watch by providing charms and tattoos

8
 at discounted prices to those who can pay and free to The cages contain three agents of the
those who can’t.
Xanathars and Zhentarim guilds who have
• She blames the rise in tension on the Watch captain,
Captain Kepesh, who can be seen reviewing his been knocked unconscious. As the party
command or drinking at the End Shift. approaches, they will see that all of them
have orange charm necklaces and tattoos on
As the party investigates the shop the
their forearms. The fourth cage holds the still
following clues can be discovered.
relatively intact undead body of Jaisa.
• Any users of arcane magic will feel its essence
suffusing the air.
Gweniver has been keeping her from
• Close examination of some of the ink that she uses will decomposing by the use magic. If awoken
reveal that some of it seems to move with a mind of its Jaisa will plead with the party to free her and
own. to stop Gweniver. Should a fight erupt Jaisa
• If a party member puts on an orange charm have them
roll a charisma saving throw which they will succeed.
will fight on behalf of the party if they can
Gwen will try to stop them from trying to put on any of free her from her cage and have a weapon for
the merchandise, however. her to use. For Jaisa use the Ogre Zombie
• If any of the party, try to detect undead they will find a
statistics from page 317 in the Monster
blip from underneath the floorboards of her shop. This
is the reanimated remains of her lover Jaisa who Gwen
Manual with the following changes.
continues to keep alive in this state because she • Her size is medium instead of large.
refuses to let go. • Her AC is 16 due to her chain mail.
• Any detect magic will determine that the orange • Her Wisdom and Intelligence scores are 10 and her
crystal charms have a strong aura from the Charisma score is 13.
enchantment school of magic and some of her living • She also knows and has prepared the following Paladin
ink has a strong necromancy aura mixed with spells; Heroism, Blinding Smite, and Cure Wounds.
transmutation. She can cast each of these twice.

SORROW’S RESPITE CELLAR THE END SHIFT TAVERN

The party can gain access to the cellar one of
One of the few nice taverns in Field Ward the
two ways a trap door that can be found behind
End Shift Tavern is where members of the
the west counter on the ground floor beneath
City Watch go to relax after their shifts
a rug, or via the cellar door on the east side of
guarding the High Road when not in their
the building. The basement if filled with
barracks. The End Shift tavern is labeled three
various cages and four tables. Three of these
tables are covered with alchemical
apparatuses and the fourth seems to be some
sort of torture table. The cages contain
unconscious kidnapped victims. Their cages
can be opened by either a key that sits on
Gweniver’s belt, a DC 20 dexterity check plus
thieves’ tools proficiency if applicable, or a
DC 25 strength check though the breaking of
the cage doors are incredibly loud and will
alert Gweniver that the party is in her cellar. on the map. Run by a relatively upbeat teifling
named Brewer the End Shift is also one of the
cleanest places in town.
Within the tavern are about five to ten
members of the Watch, but a quick glance
over the room will see that they are all rather
downtrodden. If the “Doing Your Civic Duty”
adventure hook was used, then Captain
Kepesh and two of his personal guards will be
sitting at a table near the back and after
seeing the party enter, he will wave them
over.

9
 2d8+5 members of the Watch along with
other various noncombatants. The first floor
is split into a few rooms including a large
kitchen, an infirmary, a bathroom, a
storehouse, an armory, and a general lounge
type meeting area. The second floor is split
into three main areas one half is occupied by
the beds that the members of the Watch use
to rest when not on duty, the second half is
divided between Captain Kepesh’s quarters
and the war room.

The following information can be gained from

either the Captain or any other Watch
member if the party states that they are
attempting to solve the problems that are
plaguing this section of Field Ward.
• A Watch patrol was attacked last night and all, but one
member was slain. The survivor is recovering in the
infirmary at the Watch barracks by the northern gate.
• There are rumors that should the attacks continue the THE INFIRMARY
Masked Lords may consider more drastic measure to Within the infirmary can be found a few
secure the High Road and prevent the creatures from nurses and clerics as well as the only survivor
spilling into the city proper.
of the attack on the Watch patrol, Jenkins.
• While many of the Watch do not trust her, some have
visited Gweniver at her shop. These members can be
Jenkins knows the following information and
seen with orange charms around their necks. will share it with some hesitation after some
• Three members have been talking about forming a coaxing or freely with anyone working with
hunting party and are planning to go and hunt the the Watch.
creatures that killed their friends. They can be found at
• The creatures that attacked him and his patrol were
the Square Market.
able to move through solid objects like ghosts and
If the party talk to the dragonborn he will seemed almost impervious to their weapons.
state that his name is Captain Kepesh and he • Each of the creatures had a distinct orange glow
emanating from their chest.
has no time to deal with petty problems right
• He was only saved when a cleric of Tyr came and
now. If the party say that they are assisted them with his holy magics. If he hadn’t shown
investigating the creatures he will up Jenkins is convinced, he would not be here today.
immediately give them his full attention and
After their conversation, the party will be
will tell them that he could really use their
shewed out of the infirmary by the nurses so
help. After a conversation he will direct them
Jenkins can get his rest. If the party is not
to the norther barracks to talk to Jenkins, the
working with Captain Kepesh he will confront
only survivor of the attack last night, and to
them as they leave the infirmary. He will ask
an alley northwest of the Square Market,
what they are doing there and to explain
where the attack occurred to investigate. He
themselves. If he finds their answers to be
will also state that if the party is willing to
satisfactory, he will ask for their help in
help him, he can put them up for the evening
getting to the bottom of these attacks. If he
at the northern barracks.
does not, he will have the party thrown out of
THE NORTHERN WATCH BARRACKS barracks and have a Watch member assigned
to tail them. Periodically role stealth for this
Lying just east of the northern gate the watch
guard if it is relevant.
barracks holds the small contingent of City
Watch that are assigned to guard the High SQUARE MARKET ALLEY
Road into Waterdeep proper. The barracks is
This stone paved alley lies just north west of
labeled as four on the map. The two-story
the Square Market and is marked as five on
barracks looms over the other buildings in the
the map. It was in this alley that a Watch
surrounding area. Within the barracks are
patrol was attacked last night. As the party
10
approaches the alley some Watch soldiers will investigating into Gweniver and Captain
tell them to halt and explain their business Kepesh.
here.
SURVEILLING GWENIVER
If the party decides to surveil Gweniver have
them roll a group stealth check. Everyone
should roll stealth and if the majority beat a
DC of 15 then they succeed and can continue
to surveil her. If they fail two tattooed citizens
wearing orange charms about why they are
The party can either persuade them to move snooping around. They will ask for the party
with a DC 15 persuasion or intimidation check. to come with them and will take them to the
The soldiers will move freely if they mention cellar beneath the Sorrow’s Respite and
that they are working for the Watch or for attempt to throw them into the cages. If the
Captain Kepesh. An investigation of the alley party resists, they will transform into Shadow
will reveal the following clues. Wretches and the ensuing combat will alert
• There are multiple large pools of blood that can be
Gweniver and she will come down and aid the
found. One pool is near some crates near the party in the fight before asking what they are
northwest corner of the alley. If the party has seen a doing. If Gweniver joins the fight she will only
Shadow Wretch transform it is reasonable to assume use her at will spells saving her main stuff for
that this pool is where the two Wretches transformed.
a potential combat with the party.
The second pool can be found near the grate towards
the center of the alley. The bodies of the creatures still The party can also try to gain more
lie here with the bodies of the Watch members already information on Gweniver and her backstory.
being carried off for their funeral rites. As discoverable gossip, share the following
• There are footprints that follow the pattern that
information with the party.
Jenkins said his watch performed. They were being
watched and were ambushed. • Several years ago, Gweniver’s lover was killed in a
• Investigation of the creatures’ bodies will show the mugging on the stoop of the Sorrow’s Respite.
tattered remains of tattoos from Gweniver’s shop on Gweniver went to the Watch to try and get justice but
their forearms and a strange orange crystal growth on the captain on duty Captain Kepesh refused her
their ribs. request.
• While she has not been overtly hostile to the Watch it
If the party investigates the alley around dusk is no secret that Gweniver has no love towards them
or at night have them be attacked by two and would love to see them suffer.
Shadow Wretches. • While everyone has just attributed it to the poor living

CHAPTER 2:
conditions and her emotional toil, people have been
hearing quite a bit of sobbing coming from the
Sorrow’s Respite recently.

ENCROACHING SURVEILLING THE CAPTAIN

DARKNESS If the party decides that they should surveil
Captain Kepesh again call for a group stealth

THE REVELATION:
check with a DC of 15. They will follow him
around for part of the day and will learn the
At the end of this section of the adventure the following information.
party should confirm that it is Gweniver who • The Captain is highly regimented in his daily routine
is responsible for the kidnappings and the and does a meticulous inspection of the readiness of
creation of the Shadow Wretches and be ready the people under his command.
• You see that some of the guards are taking bribes and
to confront her.
engaging in some other shady dealings under their

ADDITIONAL SURVEILLANCE Captain’s nose. He is either willfully ignorant of this or

seems to sanction it.
If your party seems confident in their • You notice that you’re not the only people following

assumption that Gweniver is the culprit feel the Captain a small group of 1d4+2 citizens are
following him as well. These people are on orders from
free to skip this chapter and continue to
Gwen to attack the Captain transforming into Shadow
chapter three which will detail the final Wretches before they do so. The attack will occur in
confrontation. If they need a little bit more of the alley and the party can either aid him or stand
a push, then have them do some additional aside.

11
CHAPTER 3: stealth roll at a DC of 15. Again, both locks
can be picked with a DC 15 dexterity check or

THE SHADOW WITCH

broken down with a DC 18 strength check,
though the latter path will make a lot of noise
and alert Gweniver to the party’s presence.
THE REVELATION:
It is clear now that Gweniver is responsible THE CONFRONTATION
for everything and she must be stopped. The As the party enters the cellar, they will find
party must infiltrate her shop and confront Gweniver standing over a Watch member who
her. is strapped to her table forcibly tattooing
them with the intent to use them as an
THE INFILTRATION assassin against Captain Kepesh. When they
The party has two main times when they can party has finished entering, she will finish
confront Gweniver in her shop; day or night. what she is doing and will greet the party
pleasantly. If the party starts a conversation
DAYTIME INFILTRATION with her, she will freely admit to being the
If the party decides to confront Gweniver one responsible and will tell them that the
during the day they can easily enter the shop. Watch has it coming to them. At this point
When they enter, she will be just finishing up there are three ways to resolve the conflict;
with a Watch member who has gotten her the party can convince her to stop seeking her
tattoo and orange charm necklace. If the party vengeance and try to help her escape, they
confronts her and starts a combat, she will can attack her at which point a massive
command the Watch member to transform conflict ensues, or they can be convinced by
and attack the party while she bolts out the Gweniver that the Watch is the real enemy
back door. She then runs and hides here and that Captain Kepesh needs to die at
somewhere within Field Ward. She will return which point they can work with her to kill
to her shop that night to gather all the people Captain Kepesh and his more corrupt guards.
under her control for an assult on the Watch Each potential path is explained in more
Barracks. The party can stop this all out assult detail below.
if they wait for her in the cellar or confront
her on her way in. If the party adopts a more
WHAT YOUR DOING IS WRONG
diplomatic approach Gweniver can be The party can talk her down and convince her
persuaded via a DC 18 persuasion or to stop through a persuasion boss battle, the
intimidation check to close her shop early. rules for this are at the end of the chapter, if
She will then ask the party to follow her to her they fail go to the second outcome and run
cellar through the trap door where she will the combat encounter. The party can make
listen to what they have to say. Depending on this a little easier if they recognize the very
what they say or how aggressive they are well-preserved zombie half-orc in one of the
refer to the appropriate confrontation path cages as Jaisa Gweniver’s former lover. If
outlined below. they accomplish this, she will beg for them to
help her get out of the city so she can start a
NIGHTTIME INFILTRATION new life. At this point the party hears boots
If the party decides to infiltrate her shop stomping around upstairs and the sound of
during the night, they can avoid any potential glass shattering. The city watch has decided
civilian casualties and stop Gweniver from to take action into their own hands and are
running. She will have two controlled sentries going to capture and execute Gweniver. Turns
posted at the front of her shop with one out she and her minions were not that
posted at the cellar doors. These sentries will stealthy when it came to kidnapping the
not transform and attack the party but if guard she has strapped to her table. Begin a
given the opportunity they will cry out and chase sequence using the rules on page 252 of
alert Gweniver to the party’s presence. The the Dungeon Master’s Guide. This will either
party can either knock out the sentries, kill culminate in Gweniver escaping or Gweniver
them, or attempt to sneak pass them by and the party being captured. At this point the
making a DC 15 deception check to gain their party can decide to either betray her, or if you
attention and then succeeding on a group are using this as part of Waterdeep:

12
Dragonheist, attempt to use their clout with armored boots above them and glass
any organizations they have, to get shattering. Gweniver will suggest that one of
themselves free. If caught Gweniver will be the party members go upstairs to see what is
executed the following week. If the players going on and if it is the watch lure them down
cannot get free, they are released after three here for an ambush. The noise upstairs is
weeks of confinement since there is no being caused by Captain Kepesh (stats can be
evidence of their participation in the crime. found at the end of Appendix B) and five
When they are released and if the “Do it for guards (Use the stats for a guard found on
the prestige” hook was used they see either page 347 of the Monster Manual). After the
Lucky or Isabella waiting for them outside of ambush Gweniver will realize what she has
the jail and over a pint of ale they will explain done and after crying tears of relief ask the
that their organization was able to pull some party to help her and Jaisa escape the city.
strings to get them their early release though Gweniver decides to burn down her shop to
now they are indebted to them. prevent her research from creating anymore
trouble. She can be persuaded by a DC 18
KILL THE WITCH persuasion check to turn over her notes
The most straightforward of the resolutions. before burning down her shop. At this point
Have the party roll for initiative, if they failed you can run a chase or not depending on if the
to sneak up on Gweniver, have three final battle was climactic enough.
transformed minions come out of the
shadows and attack the players. If they did PERSUASION BOSS BATTLE RULES
manage to surprise Gweniver her first action The party starts with three “lives”
will be to have the three captured humanoid representing their attempts to persuade
transform and phase out of their cages. Roll Gweniver, Gweniver starts with three “lives”
an initiative for them and they will escape representing her stubbornness and wanting
their cages on the next round and attack the to see the city watch suffer. The party can
party. Once combat begins the party will hear make any sort of check to try and persuade
a loud voice saying that she wants to help Gweniver, but they must justify it. For
them fight. This is the zombified corpse of example, a character may use arcana to
Gweniver’s lover Jaisa. If the party can free explain the pain that the people who she is
her have her join combat. She uses the Ogre forcing to transform feel. As Gweniver loses
Zombie statistics from page 317 in the one of her “lives” the DC of subsequent rolls
Monster Manual with the following changes. are reduced by however much you see fit. If
• Her size is medium instead of large. the party fails their check they lose one of
• Her AC is 16 due to her chain mail. their lives and the DC of subsequent rolls
• Her Wisdom and Intelligence scores are 10 and her
increases. The first group to lose all of their
Charisma score is 13.
• She also knows and has prepared the following Paladin
lives loses the “battle”. The DC for this will
spells; Heroism, Blinding Smite, and Cure Wounds. start at 20. Adjust the DC how you see fit
She can cast each of these twice. based on the players justification for their
role and their argument.

CONCLUSION:
Gweniver will fly into a rage at seeing her
lover take up arms against her and will fight
till the bitter end. After the conflict is over the
party will leave the shop and encounter Depending on the path chosen by the party in
Captain Kepesh and some of the city watch the previous chapter a few different outcomes
who are seeking a kidnaped comrade of theirs. can occur. Feel free to read the following
They will question the party and give them resolutions word for word or embellish them
some rewards and influence with the City as you see fit.
Watch for helping them stop this menace.
IF THE PARTY HELPED GWENIVER
KILL THE GUARDS ESCAPE WITHOUT KILLING CAPTAIN
With this third option Gweniver will have the KEPESH
party assist her in killing Captain Kepesh and
the other Watch members who patrol the
High Road. After the discussion that leads up
to this the party will hear the sound of
13
IF THE PARTY WAS NOT CAPTURED anything just call on him and he can help get
A few weeks have passed since you helped things taken care of.
Gweniver escape. Since then you have heard
that the city watch has accepted that a larger IF THE PARTY KILLED CAPTAIN
force needs to be patrolling Field Ward. Until KEPESH
the culprit is caught and brought to justice a It has been two weeks since you helped
strict curfew has been placed on Field Ward Gweniver get her revenge and the news of the
and special documents are needed by citizens killing of Captain Kepesh has been in the
of the city to enter and exit Field Ward. The throats of all the city criers. Along with that
High Road is now flanked by a spiked wooden news comes the news of a horrible crackdown
fence. While they oppress the people of Field in Field Ward in an attempt to find the killer
Ward, the Masked Lords have acknowledged or killers responsible. Families were ripped
their failures and there is a growing out of homes and many places of business
movement in the city to make Field Ward an were left in ruin after the City Watch was
official Ward with more resources going to it done with them. Life in Field Ward is now
in an attempt to prevent something like this much harder after the Masked Lords decided
from happening again. that a more hands on approach was needed. A
strict curfew was placed into effect and no
IF THE PARTY WAS CAPTURED
citizen of Field Ward is allowed entrance into
You walk out of the dungeons of Castle
the city proper. Special papers are now
Waterdeep having spent three miserable
needed to enter and leave the Ward, and the
weeks within them. You can still remember
few taverns have been permanently closed.
the cries of “Murderer!” and “Death to the
Rumors of rebellion have started to crop up
shadow witch!” from Gweniver’s execution as
though such an ill-advised idea would surely
if they were still ringing in your ears. It was
lead to the cleansing of the ward and a return
only by the grace of the Gods and Goddesses
to the wagon fields that it once was.
that you were not executed with her. While
the public was not allowed to witness that did
not stop the City Watch from enjoying the
REWARDS
There are several rewards that can be gained
show. After leaving with your belongings, you
from completing this quest.
magic items too, you wander back through
All total through the various encounters some
the town stopping by the Yawning Portal for a
150gp, 250sp, and 400cp can be earned from
drink or returning to Trollskull Tavern if the
various looting of the bodies and strewn
party has acquired it. If the “Do it for the
about the Sorrows Respite.
prestige” hook was used add: As you leave the
The party can gain three renown with the
Castle Waterdeep the large iron bound
following factions depending on who the
wooden gates slamming behind you, you look
party was working for. By default, the party
up to see Lucky, or Isabella, that strange
will earn membership with the Lord’s
teifling, or half elf, who hired you for this job.
Alliance and gain some renown with them. If
“Come on let's go get a drink”. They lead you
they worked with Lucky then they will gain
back to the Yawning Portal where they find
membership with the Zhentarim and earn
you all a secluded table and something to
some renown there, the same is true with the
drink.
Harpers if the party worked with Isabella.
IF THE PARTY KILLED GWENIVER Lastly for any spellcasters the party can
acquire Gweniver’s notes on her
It has been three days since your conflict with
enchantments and rituals. These are written
the revenge crazed halfling wizard, and all
in a complex code that takes four successful
seems to be returning to normal. By stopping
intelligence checks of DC in order of 25, 20,
the threat, you managed to prevent the
20, and 15. Each check reveals a little bit more
crackdown on Field Ward that the watch had
of her process. Once all checks are done the
planned though they treat the area with a
person making them acquires the knowledge
more malicious neglect. You were thanked
to make their own mind controlling totems
personally in a private ceremony by Captain
and how to make their own living ink.
Kepesh and given the promise that if you need
Descriptions of these items can be found in
Appendix C.

14
APPENDIX A: to not stray too far from the High Road and
that investigative resources were better spent

GWENIVER WILDHEART’S
on crimes within the city. Outraged by this
Gweniver returned to her shop and sought a
BACKSTORY way to get justice for her fallen love. Upon her
Guinevere Wildheart has always been an return she found a strange man in her shop
exceptional mage and kind person. Growing lamenting her plight in exchange for the
up on the Sword Coast she always heard occasional favor he would give her the power
stories of the fabulous wealth and to enact vengeance on those who stole her
opportunities in Waterdeep. So, when it was love from her, and even the power to bring
discovered through study that she had a her back for more time. Gweniver signed the
knack for magic she decided to set off and deal on the spot. Ever since she has been
travel to Waterdeep to study in the fabled City using the shadowy powers gifted by this
of Splendors. When she got there, she was mysterious man to engineer the perfect
crestfallen to discover that this supposed city response to her enemies. Now that her studies
of wealth and splendor could not or chose not are finished and her ritual is perfected it is
to care for the citizens on the outskirts. time for them to pay, and this city who stole
Determined to make a difference she set up a her heart from her will burn in shadow and
small shop where she could use what small fire.
amount of magic she had to aid the people of
Field Ward. It was during this time that she
met Jaisa, a young and ambitious half orc
who, like her, was determined to improve the
lives of her neighbors. While Gweniver took a
less direct approach, healing where she could
and engineering new potions and charms to
help where she could not, Jaisa's approach
was more aggressive. She quickly formed a
small group of likeminded citizens who would
roam the streets making sure that they were
safe to walk at night and that shops were not
burgled. Taking no money Jaisa quickly
earned a reputation as an honest and
kindhearted woman who was quick with a
joke and even quicker to protect her friends
and family. And while her reputation soared
within Field Ward that kind of notoriety also
attracts powerful enemies. The Xanathars an
up and coming thieves guild/street gang were
tired of Jaisa’s group cutting into their profits
and snatching up potential recruits, so they
decided to do something about it. Late one
night outside Gweniver’s shop a large group
of thugs ambushed Jaisa and cut her down in
the street after vandalizing the shop.
Gweniver tried to heal her but her wounds
were too intense and after minutes of tears
and consoling Jaisa passed on the stoop where
so many memories were made. Gweniver, still
a believer in justice, stormed into the End
Shift Tavern and reported to the city watch
what had just occurred. Her cries for justice
fell on deaf ears. The Xanathars had paid off
some of the watch plus as Field Ward is not a
recognized ward of the city, they had orders

15
APPENDIX B: SHADOW WRETCH
The Shadow Wretch is a humanoid that has
In this appendix you will find the stat blocks been twisted and transformed through an evil
for Gweniver Wildheart, the Shadow arcane ritual condensing shadow and malice
Wretches, and Captain Kepesh. creating an undead killing machine. Those
people who transform with an orange charm
GWENIVER WILDHEART around their necks are bound to follow the
Gweniver Wildheart is a halfling creator’s commands. If a Shadow Wretch is
wizard/warlock with chestnut brown hair that created without a command charm than it
she normally keeps up in a loose bun. She is goes on a killing spree driven mad by the
clad primarily in purples and blues. Her painful transformation it attempts to kill the
cheery outward disposition hides a sinister closest living thing and will not switch targets
purpose. until it does.

Small Humanoid Halfling, Neutral Evil Medium undead, chaotic evil

Armor Class 12 Armor Class 12

Hit Points 57 (3d6+4d8+25) Hit Points 66 (12d8+12)
Speed 25 ft. Speed 40 ft.

STR DEX CON INT WIS CHA STR DEX CON INT WIS CHA
8 (-1) 13 (+1) 12 (+1) 20 (+5) 10 (+0) 18 (+4) 10 (+0) 14(+2) 13 (+1) 10 (+0) 10 (+0) 8 (-1)

Saving Throws Int +8, Cha +7 Saving Throws Dex +5, Con +3
Skills Arcana +8, Insight +3, Deception +7 Skills Stealth +7
Senses Darkvision 60 ft., Passive Perception 10 Damage Vulnerabilities Radiant
Languages Common, Halfing Damage Resistances Acid, Necrotic, Thunder, Bludgeoning,
Piercing, and Slashing from nonmagical weapons.
Gaze of Shadows: Choose a creature within 30 ft that Damage Immunities Cold, Lightning, and Poison.
you can see, that creature makes a DC 16 Wis saving Condition Immunities Exhaustion, Grappled, Paralyzed,
throw or become frightened of you. You can spend a Petrified, Poisoned, Prone, and Restrained
bonus action each turn to maintain this effect. A Senses Darkvision 120 ft., Passive Perception 11
creature loses this status if they take damage. Once a Languages Common, Telepathy 120 ft.
creature has saved or broken free of this effect they
cannot be targeted again for 24 hours. Shadow Stealth: When in dim light or darkness the Shadow
Wretch can take the Hide action as a bonus action.
Spellcasting: Gweniver is a 7th-level spellcaster. Her Incorporeal Movement: The Shadow Wretch can move through
casting ability is Intelligence (Spell Save DC 16, +8 to other creatures and objects as if they were difficult terrain. It
hit with spell attacks). She has the following spells takes 5 (1d10) force damage if it ends its turn inside an object.
from the warlock and wizard spell lists prepared:

Cantrips: Blade Ward, Chill Touch, Eldritch Blast, Acid Multiattack. The Shadow Wretch makes two attacks with its
Splash, and Fire Bolt claws each turn.
Shadow Claws: Melee Weapon Attack: +5 to hit, reach 5 ft., one
1st-level (4 slots): Hellish Rebuke, Armor of Agathys,
Hex, Charm Person, Shield, Sleep target. Hit: 9 (2d6 + 2) necrotic damage. On a successful hit the
target must also make a DC 10 Con save. On a failed save the
2nd-level (3 slots): Ray of Enfeeblement, Earthbind, targets Strength score is reduced by 1d4 or is not reduced on a
Blur, Darkness, Hold Person, Shadow Blade successful save. The target dies if this reduces a creatures
Strength score to 0. Otherwise the reduction lasts until the target
3rd-level (3 slots): Slow, Bestow Curse, Enemies finishes a short or long rest.
Abound

16
 CAPTAIN KEPESH
Captain Kepesh is a large silver dragonborn
APPENDIX C:
who has served with the City Watch of Necklace of Charm and Control: This orange
Waterdeep for many years. For the past gem necklace is made by Gweniver in her shop
decade he has been assigned the command of and is enchanted to make anyone who wears it
guarding the High Road through Field Ward. supremely friendly towards Gweniver and
He regrets the sacrifices that he has had to forces them to follow her commands which
make in order to keep the peace along the she can either give verbally or have a given
road but is staunchly loyal to the Watch trigger. (Requires Attunement)
members that he commands and would do
anything for them.
The Living Ink: This special ink is what
Gweniver uses to force the transformation
Medium Humanoid Dragonborn, Lawful Neutral into Shadow Wretches on her selected
victims. This is enchanted ink that has
Armor Class 17 (Splint Mail)
Hit Points 73 (12d8 +18) distilled Shadow and Shadow Demon blood
Speed 30 ft. infused within. The transformation occurs
when the tattooed charm is broken either
STR DEX CON INT WIS CHA
from the ink wearing off or the lines being
18 (+4) 13 (+1) 14 (+2) 10 (+0) 11 (+2) 11 (+0)
broken. It may be possible with various
Saving Throws Str +7, Con +4 arcana checks to adjust this ink to other
Skills Athletics +5, Perception +2 various elements with Gweniver’s notes, but
Damage Resistances Cold severe research would be needed to make this
Senses Passive Perception 12
Languages Common, Draconic
transformation temporary and non-lethal.

Great Weapon Master: Captain Kepesh is incredibly skilled with

his greatsword. When he rolls for damage, reroll 1s and 2s and
take the new roll.
Improved Critical: Captain Kepesh scores a critical hit on a roll of
a 19 or 20

Multiattack: Captain Kepesh make two attacks with his

greatsword, or one attack with his heavy crossbow, or uses his
breath weapon.
Breath Weapon: Captain Kepesh can use his draconic ancestry to
exhale a 15ft. cone of cold as an action. All creatures caught within
the cone must succeed a DC 13 Con save or suffer 3d6 cold
damage on a failed save or half as much on a successful one.
(Recharges on a 6)
Greatsword: Melee Weapon Attack: +5 to hit, reach 5 ft., one
target. Hit: 12 (2d6 + 4) slashing damage.
Heavy Crossbow: Ranged Weapon Attack: +3 to hit, range
100/400 ft., one target. Hit: 5 (1d10) piercing damage.

17
APPENDIX D:
MAP OF FIELD WARD
NEIGHBORHOOD

18
19