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INTRODUCTION
Chapter 2: Trollskull Alley is the sandbox of Waterdeep:
Dragon Heist. It's where you and the players get to set your
‘own pace, create unique stories and forge a lasting
relationship with Waterdeep and its residents, You could
spend anywhere from half a session to ten sessions running,
this chapter, and neither would be too short or too long, if
‘everyone's enjoying themselves. But, as is often the case,
freedom can become overwhelming. What should you use
from the chapter? How do you use it? When? For who?
The goal ofthis document is to help you find the answer to
those questions and provide the toois to create a fun and
manageable sandbox for your players. You'll find adviee and
‘embellishments on nearly everything that’s described in the
‘chapter, which will hopefully help you DM the chapter.
It is strongly recommended that you read through
Chapter 2: Troliskull Alley before reading the resources
Included in this document, And remember: all advice is
‘optional. You know best what works at your table.
‘Meeting the Neighbors. First, you'l find advice on how
‘to handle Lif the Poltergeist, as well as two new optional
sidequests that'll help you introduce and flesh out the other
residents of Tollskull Alley.
Open for Business? Second, you'l find advice on how to
‘make the tavern renovation more affordable - and some
‘options for securing a loan, ifyour party needs it.
Joining Factions. Third, you'll be given reviews of each of
the factions available to the players, so that you can choose
the right factions for your party.
Downtime Options. Fourth, you'll ind inspiration on how
the downtime options presented in the Xanathar’s Guide to
Everything can be altered and flavored to fit with Waterdeep
and the campaign
‘Making a Plan. Lastly, everything is brought together and
you'll be given general advice on how to plan and organize
‘chapter 2, so that i's manageable and well-paced,
A Quick Worp oF ADVICE
If you're in doubt about how to go ahead with this chapter,
talking to your players about it might be the best way.
forward, After receiving the deed to Trollskull Manor, let
them know what's about to happen: they're going to have a
period of downtime, where you'll present them with
‘opportunities for minor quests and scenarios, but It's
‘otherwise up to themselves to decide what they're doing. If
you have the books, you can show your players the various
‘downtime options in the DMG and XGtE for inspiration. You
‘can also tell them to let you know about places or people in
the city they might want to visit, as well as factions or stuff
from thelr background they want to expl
The point is to get a headstart on the preparation, and it
obviously works best if you end a session just before
beginning on Chapter 2, This allows your players to tell you
about the endeavors they'd like to pursue before you sit
down at the next session. You can’t always control when a
chapter ends or begins, but it's worth keeping in mind,
Lastly, remember that this is first and foremost your
players’ sandbox. Ifyou've planned for a specifi character to
bbe approached by a specific faction, but they suddenly want
to go with another faction, let them make that choice for
themselves, Also, don't overuse the sidequests. If your
players have strong ideas about what they want to do,
consider skipping some of the sidequests oF missions you
had planned for them, And, most important: have fun,
MEETING THE NEIGHBORS
Waterdeep: Dragon Heist has one of the best ideas of any SE
DAD Campaign so far: give the characters a base early. A
place they can call home, The campaign book gives a lot to
work with in the description of Trollskall Alley and its
inhabitants in Chapter 2, Below, well elaborate and expand
fon this information, giving you additional tools to make
Trollskull Alley a vibrant and exciting home for your players.
Sprrit on Tap
Before the characters can get on with anything else in this
chapter, they'll first have to deal with Lif, the half-lf
poltergeist (a variant specter, that is invisible and has
‘other attacks) who haunts the Trollskull Tavern
I you simply introduce Lif as a mute, invisible force of evil
that throws plates, slams doors and writes rude messages on
dusty surfaces, it's likely that the characters first notion will
be to destroy him, That would be a shame, since having a
ghostly bartender is honestly pretty awesome. So, if you want
to steer the party towards keeping lif around, you can have
Volo warn the characters about the poltergeist (or
accompany them on thelr first visit), The old chronicler
‘might say something along these lines:
‘Oh, yes, I almost forgot. There's supposedly a poltergeist
living = eh, | mean ‘residing’ - in Trallskull Manor's taproom. As
far as I've been able to gather, it's a former bartender, a halfel)
‘named Lif, Half the reason I bought the place, realy. You see,
'mwriting a book on such spirits...Ab, well, that's neither here
nor there. From what I've heard Lifis quite possessive -no pun
intended - but not malicious. Seems lke he just misses his old
job, is what I've been told. Perhaps fixing up the place is
{enough to.get on his good side.
‘You can make the good advice more or less obvious, as you
prefer A variant of the above should at least ensure that the
party considers keeping Lif around - and that they know
‘what they're dealing with when they find Lif throwing chairs
and writing ‘Closing time!’ on the grimy windows,
If the party does decide to fix up the tavern (see the ‘Open
for Business?" section of his document for more information
‘on that), you can describe how Lif starts out hindering the
efforts - toppling crates and smashing plates - but eventually
helps the party with the renovation ~ hanging up paintings
and fixing chairs - as the weeks progresses. This is also a
good opportunity to give Lif some personality. You can have
him continually put up a particularly bad painting of an elven
girl, even ifthe party takes it down, or have him roughly tear
fof the shoes of anyone who drags mud, rain or snow into the
newiy renovated tavern A bit of personality goes a long way
to becoming a dear member ofthe troupe,
STEEL AND Woop
Disclaimer: This sidequest touches on topics of homophobia,
lass and loneliness. you think that any of your players are
‘uncomfortable exploring these subjects, skip this one.
If you want to get your party more involved with their
neighbors, you can use this small sidequest to draw them in,
Talking with the Genasi, ‘The quest starts when the
party either visits Steam and Steel (T3) or Embric and Avi
Visit the party at Trollskull Manor to welcome them to the
neighborhood. As the genasi couple speak with the party, Avi
eventually leads the conversation to Talisolvanar ‘Tally’
Fellbranch, the half-elf owner ofthe Bent Nail (T2)Have you met Tally yet? The owner ofthe Bent NaiP" the
blue skinned water genasi asks. Before you can answer,
Embric rll his eyes and says: "By Kossus' flame, why can't
you just lett go?”, Avi sends a teasing glare his partner's
way. "Dor't flare up now, darling. I'm just making
conversation with our new friends.” He turns back to you
''m just wondering what your impression is of him. We've
been trying to get into business with hr, but it seems.”
(Once again, Embricinterjects: "He doesn't lke that
together. Fine, We've fa
ed ignorance before. I's nothing
new - won't waste any more of my time speaking of it!"
Embric storms off after this. After he's left, Avi explains that
the couple invited Tally over for dinner a few weeks ago to
discuss a business proposition: make products of steel and
‘wood together, combining their efforts for the benefit of both
shops. The dinner started well, but as the night progressed,
‘Tally seemed uncomfortable at the displays of affection
between the two genasi, In the end, he flatly rejected the offer
and left before even finishing the exquisite Calishite
chocolate-cake Embric had made! Tally has been cold and
dismissive with them ever since, and while Embric says he
doesn't care, Avi knows his feelings are hurt. The water
‘genasi, however, isn’t sure that Tally is actually a bigot, Avi
asks the party to help him find out what offended Tally, and if
there's any way to make the half-elf reconsider. As thanks, he
offers a 20% discount on the Steam and Stee!'s inventory,
Talking with Tally. Tally can be found in bis shop (72)
whittling away at a wooden cane, The middle-aged hal-elf is,
friendly and courteous, but ill take a DC 10 Charisma
(Persuasion) check to get him to open up about the genasi
Tally puts down the cane he's working on and sighs heavily
know they think it's because I dont lke them being
together, but t's not that.. Or, well, n a way its. You see
used to be married. Her name was Isolla. The most brillant
and beautiful wornan I've ever met. But she was human, We
had many great years together, but while I just greyed abit
atthe temples, she grew old and eventually. t's been
several years now, and I thought | haé moved on. But, seeing
the two of them together, so happy and so perfect for each
other, just hurts too rnuch. If we went into business
together, I'd have to see that everyday. | can’t bear that But
how do you explain to someone that
them, because they're too happy? That's not fair either.”
fou can't be around
Resolution. Simply getting an explanation fulfils Avs quest.
But, the party might want to help solve the problem as wel. If
the characters have great ideas on their own, let them run
with those. Otherwise, you can have a character with
Proficiency in Religion remember that the Temple of Sune,
the goddess of beauty and love, regularly holds sermons
‘where widowers can meet, mourn and mingle, often resulting,
in new, beautiful unions, You can also have Avi come up with
the idea, when the party explains what Tally told them.
With a little persuasion (a compelling argument like: “I
think that Isolla would want you to move on and be happy"
should suffice), Tally will agree to attend one such sermon,
You can put a sweet lttle bow on the whole ordeal by having,
Avi and Embric show up at the Manor with a smiling Tally,
land an elven woman a few weeks later - just to give thanks to
the party before heading out fora couples’ dinner!
PAPER PROBLEMS:
‘Troliskull Alley is also home to two more magical shops:
Corelion's Crown (T4), where the wood elf Fala Lefalir sells
potions and remedies, and Book Wyrm's Treasure (15),
‘where Rishaal the Page-Turner sells books and spelisrolls,
Fala’s Protest. This small quest starts when the party one
day finds the wood elf Fala protesting outside Rishaal’s shop.
Fala is holding up a sign that says "Duskwood paper =
“Murder!” while ranting at anyone who walks past the Book
Wyrm's Treasure; "They use Duskwood for their spell scrolls
here! Did you know that a tenth of all Duskwood trees are
chopped down each year? Soon there'll he none left!
If the party speaks to Fala, the wood elf fervently explains
how they recently found out that Rishaal Is using the rare
Duskwood for his spell scrolls. Fala intends to remain in front
of the shop until he stops, While the partys talking to Fala,
Rishaal comes out the shop: "Please don't let this charade
scare you away. Come inside -I could use your help
Talking to Rishaal. The gold dragonborn isnt big on the
environment, but Fala’s protests are beginning to hurt his
business. Ifthe characters come inside to speak with him, he
laments the wood e's protests: “I understand the concerns
about Duskwood, but I don't have other options. I's the only
paper I can get that is of high enough quality. My customers
expect no less from me. Meanwhile, Fala’s ruining my
business. If you help make the protests stop, I'll let each of
you pick outa book or scroll at half price!”
Changing Papers. The most obvious, non-violent way to
make Fala’s protest stop, is to find another sort of paper for
Rishaal's scroll. A character can make a DC 10 Intelligence
(Arcana) check to remember that there are some quality
alternatives to Duskwood, However, suppliers are few and far
between - and only other wizards are likely to know one,
Depending on who they've met or which factions they've
joined, the party may already know - or can be pointed
toward - one of three notable wizards from appendix B:
Skeemo Weirdbottle (Zhentarim), Remallia Haventree
(Harpers) and Vajra Safar (Force Grey). You can also have
Volo suggest one of the three if they come to him for ald
‘Meeting Skeemo, The party can mect Skeemo at his
potion-shop ‘Weirdbottles Concoctions’. The zhent deals
‘mostly in potions, but does still buy shadowtop-paper for his
personal use. Hell put Rishaal in contact with his supplier if,
Rishaal shares some of his more powerful spells with him.
Rishaal is loathe to share magic with the disreputable Zhent,
bout will do tif the party recommends it
‘Meeting Remallia. Remallia welcomes the party to her
‘manor. She'll gladly share her laspar-supplier with Rishaal,
but expects him to report to her if anyone buys powerful
‘magic from his shop. Rishaal is reluctant to agree to this, but
of the three options this one is the most palpable to him.
‘Meeting Vajra. Vajra speaks with the party inside the
blackstalf tower. She'll put Rishaal in contact with her
zalantar-supplier only if he promises he won't sell magic to
known Xanathar Guild members, Rishall will reluctantly
agree, although hell miss the Xanathar’s gol.
Resolution. How much or how litte the party is involved
Jn the negotiations is up to them ~ maybe they'll just put
Rishaal in contact with the other wizards, or maybe they'll
get offers from each and broker a deal. Maybe theyll find
Another creative solution, The most important thing is that
they meet the neighbors and perhaps other important NPCs.
If they manage to get Rishaal to switch papers, Fala stops the
protest and is, like Rishaal, grateful for the party's aid,
offering permanent or temporary discounts on their wares,SSsSsSsSSsssSsssssssess
Mirt 'The Moneylender’
As his nickname reveals, this retired adventurer is
no stranger to lending people money.
‘Meeting Mirt. The party might've already met
Mie, ifyou used him as suggested in our product
coveriny ‘A Friend in Need, If not - or
RENOVATING THE TAVERN ifthe characters dont think of him « hell be
mowing the Tuvan Kooohg Expense Te Renaer Neverembers frst suggestion. When the
party meets Mirt in his sprawling manor, he'll
greet them io his usual. flamboyant” and
OPEN FOR BUSINESS?
One of the mote interesting aspects of Chapter 2: Trollskull
Alley is the opportunity for the party to refurbish and run the
‘Trollskull Tavern, However, there are some Issues with this -
as well as some points that can be enhanced and improved.
So, following the "Tavern Keeping Expenses'-sidebar in
Chapter 2, you'll find that renovating the tavern takes 12 days
and costs a hefty 1,250 gold pieces, including guild payments. Braggadocious manner. When he hears about the
First off, there's the time. 12 days is a weird number of tavern he'll exclarn, "Ever since that lazy dullard
dlays, when nearly all other downtime activities is handled in Duman bought the Yawning Porta, Ive. been
five- or ten-day-increments, Ifyou want to make things nice wanting to have my own tavern. Now youre
and simple, you can shorten the renovation period to 10 days telling me | can own one without any of the
Secondly there's the costs. 1,250 gp isa huge sum for 2nd glass-cleaning and chair-stacking that old fool is
level adventurers, Unless your party ransomed Xanathar's spending his days with? Well, count me in!"
goldfish or mugged Durnan during chapter 1, they're not Lending Money. Mirt doesn't want to lend
money -he wants to invest. He'll take a 5% share
of the tavern's profits for each 100 gp he gives
the party (with a complete repayment of his
investment. after a year, if the profits aren't
coming in fast enough to his liking). A successful
DC 15 Charisma (Persuasion) check can get him
down to 2,5% per 100 gp - a character affiliated
likely to have that kind of coin ff you don't want that detail 0
stop your party from living thelr dreams, we've outlined
‘some ways the party can acquire the necessary funds below.
REDUCING THE costs
If the party wants to renovate the tavern, and you want to
enable them, but they don’t have the funds, you can first try with the Harpers has advantage on this check,
to cut down the costs. For each player helping out in the Developments. If the party gets into business
renovation, have them roll an ability check for each 5 days with Mirt, he'll regularly ‘check in’ to see how ‘his
they spend renovating the tavern, Here are some examples: tavern’ is doing, making outrageous suggestions
‘or bringing gifts ("You really should see about
+ Strength (Athletics) - The character moves furniture, mounting a dragon's head over the fireplace -
clears debris and repairs stuf. that would draw in crowds!" or "Well, is it really a
+ Dexterity (Sleight of Hand or Stealth) - The character tavern if you can't enjoy an Ilthid's Kiss?”
steals silverware, spirits and other stuff forthe tavern.
+ Charisma (Deception, Intimidation or Persuasion) ||
The character bargains better deals for provisions.
‘+ Spelicasting Ability Check - The character uses magle
‘0 assist with the renovation.
Ifa character wants to cast specific spells to aid the effort Istrid Horn
(uch as using mending to repair stuff or charm person on ‘The shield-dwarf Istrid Hom is the Master of
supplier), refer them to the Spelicasting Ability Check, Trade ond Coin forthe Zhestorins Doom elders
tunless you feel an idea is good enough to warrant an ‘Meeting lst the party have had dealings
automatic success or a more specific result, For each check, with the Ehertarim, they might fn their way £0
lower the cost of the renovation by 10 gp for a result 10 o Istrid on their own’ Otherwise, Volo will suggest
higher, by 25 gp for a result of 15 or higher, and by 50 gp for a talking to Istrid Horn about securing a loan. The
result of 20 oF higher, as you describe how the characters! characters can find her ina heavily guarded
efforts ald the process. warehouse on the docks, where the dwatf will
shrewdly assess the party's business plan.
BorROWING THE MONEY Lending Money. \strid Horn will loan up to
ven with lowered costs, the party still might not be able to 2,500 gp at 10% interest per tenday. The first
failure to meet a payment adds 10% to the
amount owed. "The second failure? Well, let's
just hope that ye don't have to find out, eh?". She
won't budge on these terms, except if a
character is a Zhentarim member or signs up to
be one, in which case she'll only demand 5%
afford the renovation. Luckily, a city as large of Waterdeep
hhas plenty of people wholl be able to lend the party what
they need, Including - but not limited to - Mirt ‘the
‘Moneylender’ and Isteid Horn of the Doom Raider Zhentarim
both described in the sidebar.
If you want to make sure the party realize they have this, interest per tenday,
‘option, have both Renaer and Volo accompany them when Developments. If the party gets into business
they first visit their property in ‘Trollskull Alley. Both to with Istri, she'll send a couple of her goons
‘quickly gauge the cost of the renovation - "likely more than a down to the tavern at the end of each tenday to
41,000 dragons, all in all!” - and to suggest Mirt and Istrid collect her dues. If the party fails to pay her
Horn respectively. You can also use other wealthy and twice, the goons will start breaking stuff and
notable NPCs, such as Vajra Safabr, Jarlaxle or even the taking valuable inventory. If the characters are
foolish enough to fight back, the Doom Raiders
themselves might get involved,
—_
Cassalanters, if you think ieTl ft your campaign, Allow the
party to first find out the final cost of the renovation before
deciding the precise amount they'll borrow (as ia,
lender just ponies up the amount of gold needed when the
renovation is done),RUNNING THE TAVERN
So, the party manages to get the necessary gold and can call,
themselves owners ofa tavern inthe fanciest part of town, So
hhow does that work? We get some help from the campaign
book, which describes the following:
‘+The regular expenses are 60 gp per tenday.
‘+ At the end of each tenday, the party rolls 14100 + 10 on
the "Running a Business'table in the DMG (p. 129) to
determine losses or profits.
‘+ The party can increase the roll by 1 for each 1 gp they
spend on promoting their business during that tenday.
First, a quick look at the math for this. Rlling 14100 + 10 on
the table each tenday comes out to an average of 6.5 gp of
profits per tenday, or a whopping 6 sp and 5 cp per day. Not
‘exactly a booming business. Investing in promotion increases.
the returns a bit. The sweet spot is around 30 gp, which
makes the average profit soar to almost 20 gp per tenday. I's
better, but let's still not hope the party were thinking they
could pay Istrid Horn back solely with coin from the tavern!
While these rules are functional, they could be more
flexible, inspiring, and - to be perfectiy honest lucrative, I's
also important to note that the way it's described in the
chapter, it seems like the party gets to roll on the table
whether they actively spent downtime overseeing business
‘with the tavern or not. That's probably good, since the party
‘won't always be around to keep it running. However, we're
rot told what happens if the characters actually spend their
downtime working in the tavern,
So, let's take a look at how we could change and enhance
these rules
A RISKY PROMOTION
With the current style of promotion, you simply add 1 to your
roll foreach gp spent, resulting in around 30 gp always being
the optimal investment, And, while 30 gp increases average
profits, ¢ actually decreases the maximum potential profits in
given tenday (because while you are more likely to roll 91+,
youstill only get 3410 x5 outof it, when you do}
If you want a variant that instead increases the potential
risk as well as the potential reward, you can use the following,
rule for promotion:
‘+ For each 10 gp spent on promotion, increase the profit
multiplier by 1, toa maximum of 10. Gold spent this way
is counted as part of the regular expenses.
When handling promotion this way, you can potentially
double the maximum gold the tavern can earn ina tenday (by
increasing the number you multiply with when rolling 61 oF
higher on the ‘Running a Business'-table), But remember,
because the promotion costs are a part of the regular
‘expenses, they are also multiplied ifyou roll poorly
Now, this way of using promotion actually comes out to a|
litde less average profit than the regular method, but it gives
‘a much bigger variance. To really maximize gold spent on
promotion and create a truly successful business, the
characters will hve to get involved themselves.
Purrine IN WorK
‘As mentioned above, the rules we're given in the chapter
don't specify how the party can help make their tavern
succesful (except for spending gold on promotion). Below
‘we'll resent some rules for handling that,
‘After the party has decided how much coin to pour into
promotion, each character that spends their downtime on the
tavern can make a skill check related to the job they're doing
for each 5 days sper
working. Examples include
+ Bartending: Dexterity (Sleight of Hand), Charisma
(Performance/Persuasion), Wisdom (Insight)
+ Management: Intelligence (Investigation), Charisma
(Deception /Intimidation/Persuasion), Wisdom (Insight)
+ Entertainment: Charisma (Deception/Performance),
Dexterity (Acrobatics/Sleight of Hand)
+ Promotion: Intelligence (Investigation), Charisma
(Performance/Persuasion), Wisdom (Insight)
+ Security: Strength (Athletics), Charisma/Strength
(Intimidation), Charisma (Persuasion).
Allow the players to be creative with their jobs and the
skillchecks they use, as long as it makes sense, If they use
‘magic to ald them in performing their job, they can make a
spellcaster ability check in place of a skill check. If you want
to, you can also require that a character who works at the
same job for an entire tenday must choose two different skill
checks to perform.
‘When the players have decided on which jobs they're
performing and what skill checks they're making, they roll
the skill checks, Depending on their rol, they'll get a bonus
when they roll to determine the losses or profits for the
Skill Check Result Bonus
10-14 8
15-19 +5
20+ +10
When the bonuses for each character's skill checks have
been tallied up, this combined bonus is added to the 1100 +
410 the players roll on the ‘Running a Business'-table at the
tend of the tenday. So, for example, if two character's each
spend a tenday of downtime working on the tavern, they roll
‘two skill checks each, One character rolls @ (+0) and 17 (+5),
while the other rolls 12 (+3) and 22 (+10), for a combined
bonus of +18, So instead of only 14100 + 10, the party rolls
1d100 + 28 on the ‘Running a Business'table when
determining the tavern's profits or losses at the end of the
tenday,
Combining these rules with the A Risky Promation’rules,
you get some more dynamic rales, with higher risks, but also,
‘a much higher potential reward for the players, whenever
they involve themselves in running the tavern,
VARIANT RULES - SUMMARY
To summarize, the variant rules are:
+ The regular expenses are 60 gp per tenday.
+ Promotion can be added to the regular expenses. For each
410 gp spent, the profit multiplier increases by 1 (max 10},
+ Ifa character spends downtime working on the tavert
they roll a sklleheck for each 5 days of downtime spent,
Each check gives a bonus to the on the "Runnin a
Business'table (10-14 = +3, 15-19 = +5, 20+ = +10)
+ At the end of each tenday, the party rolls 14100 + 10 (+
the bonus from characters who spent downtime working)
fon the ‘Running a Business'-table in the DMG (p. 129) to
determine losses or profitsJOINING FACTIONS
One of the most entertaining aspects of this chapter is the
‘opportunity for your characters to get involved with various,
factions, Use this to strengthen their bonds with important
NPCs and get them more involved with events in Waterdeep.
But, deciding which of the factions to use can be difficult, so
fon the following pages you'll ind a brief deseription and
‘evaluation of each faction your players can join up with.
Be aware that most ofthe combat encounters inthe faction
missions are very easy ithe entire party is tagging along. To
keep things entertaining, you can scale things up or down
‘depending on how many characters are along for a mission.
BREGAN D'AERTHE
Bregan Diaerthe is a company of mercenaries led by the
dastardly Jarlaxle Baenre. They are scrupulous and ruthless
as they work to grow their influence on the surface. IF Bregan,
Diaerthe had an alignment, it'd probably be chaotic neutral,
EsTaBLisHinc Contact
If you go by the book, Bregan D'aerthe only makes contact if
drow characters spot the mercenary band survellling them,
‘Then Jarlaxle shows up in a disguise and gives the missions
‘This presents some issues, however.
rst, regan D'aerthe will only approach drow characters,
preferably male, So, if there's no drow in the party, there's no
Brean Daerthe. However, over the centuries Jarlaxle has
made several exceptions to this rule, allowing several
‘humans and dwarves to beomce member. It wouldn't be too.
‘outlandish for Jrlaxle to select a non-row character with
panache and questionable morals for membership.
Second, an almost impossible 18 passive perception is
needed to spot the survelllance. Instead, you can allow 2
character to make a DC 18 Perception check for each of three
days of surveillance (without explaining why), and have
Jarlaxle show up even ifthe surveillance isn't spotted,
Third, the book doesn't mention what the "haberdasher J.B
Nevercott’ tells the party, that would make them perform
dubious missions for an unknown entity. I's also a bit,
disappointing to not actually use the real Jarlaxle, when he's
such a fun character. You can have him meet the rest of the
party in disguise, but drop it in front of any prospects, before
informing them what Bregan Diaerthe is and offering
membership. To protect his cover, hell deliver a thinly veiled
threat: "We value discretion highly. That goes for my own
person as well best to just know me as .B. Nevercott. People
‘who speak too loudly of us have a habit of going.. silent.
BREGAN D'AERTHE Missions
The first three missions given by Jarlaxle are quite simple.
But the fourth mission is one of the most daring and exciting
‘of any faction: an assassination inside the Xanathar's lair
None of the missions require a huge amount of work on
your part, since the missions that involve combat already
hhave maps and descriptions in the book. The missions are
also compatible with all factions except the Xanathar's Guild
SHoutp You Use Tus Faction?
If you have drow or half-drow in the party, or a non-good
character who hasn't thrown their lot in with the Zhentarin,
using Bregan D'aerthe is a good bet. I's a fun faction, albeit
only the later quests have meat on them, Remember,
however, things could get awkward (not necessarily in a bad
way) ifyou also choose Jarlaxle as the main antagonist!
MERALD ENCLAVE
‘The Emerald Enclave is 2 loosely organized network of
ddrulds, rangers and other nature-lovers, who work to
preserve the natural balance. Ifthe Emerald Enclave had an
alignment, 'd probably be true neutral.
ESTABLISHING CONTACT
The Emerald Enclave is fairly straight forward about
establishing contact. A white cat slips by with an address, the
prospects meets with a halfelf groundskeeper and a
disembodied demigod, and they're good to go.
EMERALD ENCLAVE MISSIONS
‘The Emerald Enclave missions are all centered around
confronting and destroying unnatural beings, so it's quite
thematically strong, although not too tied to the story. I's not,
the most compelling missions in terms of encounters and
actual roleplaying, All the encounters are also weak for their
level, so you could consider beefing them up abit,
‘The missions will require a bit of work on your part,
especially i you prefer to use maps for your encounters, They
are, however, compatible with all other factions, except for
the Xanathar’s Guild
Suoutp You Use Tuts Faction?
Using this faction can feel a bit forced, since Waterdeep:
Dragon Helst is an urban adventure. However, if you have a
character that fits the bill or who has expressed an interest in
joining the Emerald Enclave, you should of course give them
the chance to do so. But you won't miss much in term of story
or content ifyou don't use the Emerald Enclave.
Force Grey/Gray Hanps
This faction is local to Waterdeep and works to protect
Waterdeep from threats the City Watch and City Guard aren't
sulted to handle. If Force Grey had an alignment, it'd probably,
be lawful or neutral good.
ESTABLISHING ConTAcT
Vajra Safahr doesn’t mess about. Why ask, when you can
orden. She's straight forward and insistent, which is
refreshing, Not much to think about here. The book doesn't,
mention, but it seems fitting that Vajra Safahr would single
fut arcane spelicasters or soldier/guard-types to be
prospects for the Gray Hands,
Force GrewGray Hanps MISSIONS
The Force Grey missions are great fun and thematically
fitting, The first three involve diplomacy and investigation,
while the fourth mission isa foray into the Xanathar's Lae!
‘To really make the missions good and entertaining will
require some work on your part. You'll probably want to flesh
‘out a fun conversation with a bronze dragon and maybe put
some extra steps into the investigation of Meloon
Wardragon’s behavior, Once again, the missions are
compatible with all factions except the Xanathar’s Guild
Suoutp You Use Tuts Faction?
Tn most cases, yes. I's the perfect faction for any character
that might not fit perfectly into other factions - or even for
the entire party, if you only want to use a single faction. It's
not heavy on combat, but the quests are fun little excursions
and the rewards are very nice, It’s also a big plus that the
faction is local to Waterdeep and thus more entrenched with
the adventure asa whole,HARPERS
ORDER OF THE GAUNTLET
‘The Harpers are 2 loosely organized network of bards,
‘wizards and good-aligned folk, who work to protect common
folk from tyrants and oppressors. If the Harpers had an
alignment, itd probably be neutral or chaotic good.
EsTaBLisHING ConTact
‘This is a fun one, Mirt is excellent if played to his strengths
land a meeting at an opera is very Hond'esque. You probably
‘won't have to force the characters to attend this meeting,
HARPER MISSIONS
‘The Harper missions vary greatly. From talking to a spying
horse to exposing Jarlaxle at a party. Be aware that the first
‘quest is somewhat incongruent with everything else we
Jnow about the Zhentarim (Yagra Stonefist and Davil
‘Starsong are opposed to Manshoon's faction of the Zhentarimn
precisely because they don't want a fight with the Xanathar's
Gulld). Instead, you can have the horse overhear the two
talking about the return of Manshoon - or replace them with
Urstul Floxin, Second, the DC 24 Insight check needed to
‘complete the fourth mission is neatly impossible at Sth level
The missions are fairly detailed, but will require some
‘work on your part especially in creating a house party if
you want it to be entertaining. The Harper missions also play
badly with both the Zhentarim (Ist mission) and Bregan
Diaerthe (4th mission),
SHoutp You Use Tus Faction?
I you've read any Forgotten Realms novels, you've probably
run into the Harpers more times than any other faction.
‘They're a great, fun and varied faction. Mit is a fun character
too, being an rotund drunkard with a big mouth and the
resume (and skills!) to back up his boasts. However, because
‘the missions step on the toes of other factions, you may want
to either alter or replace some of them, so you don't cause
strife with characters aligned with those factions.
Lorp's ALLIANCE
This confederation of cities and towns in northern
‘work to protect the interests ofits members and ensure free
unhindered trade, If the Lord's Alliance had an
alignment, itd probably be lawful neutral
Faerun
ESTABLISHING GoNTACT
‘The book doesn't really say how falester Silvermane
establishes contact, so you'll have to decide for yourself. It
‘can be as easy as him just showing up atthe front door
Lorp's ALLIANCE MIssIons
The first two missions involve some f
easy combat
encounters, while the third is a more interesting (and,
potentially deadly) scenario, and the fourth is a simple
investigation handled with dice rolls:
The missions will require some work on your part, mainly
‘when it comes to the combat encounters. The second mission
pits the party against Xanathar's Guild, while the third and
ourth mission creates problems with the Zhentarim.
SHoutp You Use Tuts Faction?
‘The missions are decent - especially the third one - but the
faction is otherwise pretty bland. It meshes badly with the
Black Network, so you're probably best off skipping this one
ianother character has alread jolned up with the Zhentarim.
‘This order of clerics, monks, paladins and other pious people
work to destroy evll anywhere they find It. Ifthe Order of the
Gauntlet had an alignment, itd probably be lawful good,
ESTABLISHING CONTACT
Savra Belabranta is an interesting character, and while her
approach is straight forward - showing up and asking
potential prospects to follow her to the temple - the
ceremony is mare than mast other factions require,
OppER OF THE GAUNTLET MISSIONS
‘The missions are interesting, From stopping fights to chasing
splined devils. Most interestingly, they also get the party
Acquainted with the Cassalanters, as one ofthe only factions.
They will require some work on your part, especially when
ft comes to making maps, but aren't the most intensive. They
also don't step on the toes of other factions.
Suouxp You Use Tuts Faction?
‘This faction is pretty select when it comes to choosing,
members - Helm, Torm or Tyr worshipers, paladins, lawful
clerics and 50 on. so it makes little sense using them without
any of those in your party. If you are going with the
Cassalanters as the main villains, the Order of the Gauntlet
becomes an even better choice, since the missions will mesh
well with the story.
ZHENTARIM
‘faction divided in Waterdeep, the Black Network is a wide-
spread shadow organization involved in many legitimate and
less-than-legitimate businesses across the north. If the
‘hentarim had an alignment, i'¢ probably be lawful evil
ESTABLISHING ConTACT
flying snake and a meeting at the Yawning Portal. I's likely
the party has already had some interaction with the
‘Zhentarim, and the Doom Raiders specifically (the very first
encounter involves agra Stoneflst, so it’s nearly
unavoidable), so Davil Starsong and his buddies have had a
{good chance to pick out the right prospects.
ZHENTARIM MISSIONS
All four Zhentarim missions are surprisingly benign, Or
maybe not surprisingly, considering we're told that Davil
Starsong’s Zhentarim pursues more legitimate avenues than
Manshoon's more murderous branch of the organization,
Either way, stopping a renegade drow gunslinger, delivering a
Dit of poison (alright, that one is morally questionabale),
finding a noble halfing-turned-wererat and killing a traitor
isn’t that bad. And, they're all pretty fun to boot - the last
could even take the characters into Kolat Towers
‘The Grst and last mission will require a bit of work, but
otherwise the missions are fairly. straight forward.
Additionally, they won't - also surprisingly - run the party.
‘afoul of any other organizations. Even the drow being hunted
isa renegade, so Jarlaxle probably wouldn't mind.
SHoutp You Use Tuts Faction?
Sure, While the Black Network has a bad reputation, this
band of Zhentarim are far from the worst Waterdeep has to
offer [ell work with other factions and even if there's good.
aligned characters in the party. Plus, the Zhentarim are in the
center of the adventure, regardless of how you play it, so
getting the party involved with them is not a bad idea,DOWNTIME OPTIONS
Since downtime activities are very likely to become a factor
in this chapter of Waterdeep: Dragon Heist, well give a brief
‘overview and evaluation of each downtime activity presented
inthe Xanathar's Guide to Everything (p. 123), as well as,
advice on how to fit them to Waterdeep and your party,
Buyinc A Macic ITEM
Ina city as large as Waterdeep, this is an obvious option.
However, a 2nd-level party probably isnt rolling in funds, so
you shouldn't be too worried about what they can dig up.
There are plenty of different places to buy magic items in
Waterdeep, but if you want to make it interesting and tie it to
the story - and pethaps foreshadow some ofthe later content
= consider Skeemo Weirdbottle, the Gralhunds, the
Cassalanters,Jarlale (in disguise), Nibiloor (through a brain
‘washed proxy), or even Vajra Safahr as potential sellers and
roleplay the meeting, Consider the same for rivals, if a
character rolls a complication,
CAROUSING
‘This is a fun option, and an opportunity for you and your
players to plant seeds for later in the campaign,
You can tie the contacts the party makes to the story by
using names from within Manshoon’s Zhentarim (low-level
{goons include Sidra Romelr, Manafret Cherryport and Yorn
the Terror), the Xanathar's Guild (low-level goons include
Samara Strongbones, Flutterfoot Zipswiggle and Ott
Steeltoes) or the Cassalanters, ifthe party are partying with
‘the upper class (low-level goons include Jandar Chergoba,
TTissina Khyret and Laiba "Nana” Rosse). Having a contact,
within a faction doesn't mean that person will do anything t
aid the character, but it might come in handy if the party
meets them during the later stages ofthe adventure,
CRAFTING AN ITEM
‘This option may come into play, but remember that crafting
magical items - which, le’ be honest, s probably what the
characters will want to do - requires a face-off witha sizeable
‘monster Ifa player expresses interest in doing this and you
‘want to put some effort into it i's a good way to create a
‘mini-sidequest for the party, where they face a dangerous
‘monster like a displacer beast in the sewers, or something,
similar, to that they can create an awesome magical item,
CRIME
‘Now this is a fun one. And, potentially a very rewarding one
Or avery punishing one. Bither way, a fun one!
To make it fit with the party, you can try to think about
who the target could be (or have the character decide
themselves!) A struggling merchant? Could be Emmek Frewn
(ee the Business Rival section in Chapter 2). A prosperous
merchant? Could be Durnan (owner of the Yawning Portal) or
‘even one of the neighbors from Trollskull Alley! A noble?
Why not the Gralhunds, the Cassalanters or the Rosznars (the
Black Viper's family, see Appendix 8)? One of the richest
people in town? Could be Mirt or Remallia Haventree!
GAMBLING
This is also a player favorite. Put gold up - get gold back (or
lose it, but let's not talk about that). Gambling is also readily
available in Waterdeep,
So, where does one gamble in Waterdeep? There are some
interesting options, which you - or the player - can choose to
enhance the experience, Ifi’s for a smaller amount, it could
be down on the docks (perhaps back at the Skewered
Dragon), or if t's for larger amounts, it could be aboard one
of Jarlaxe's carnival ships or at Tymora's Fancy, a gambling
den run by the infamous elf Elaith Craulnober.
Pir FIGHTING
A fighter or barbarian’s dream, pit fighting ~ which is
organized, non-lethal forms of combat for prize money - is
also readily available in Waterdeep.
‘There are many places a person can fight for money in
Waterdeep, yet none mentioned by mame in Volo's
Enchiridion, Consider unsanctioned fights in bars and
taverns (which the city watch usually ignore) or celebrated
bouts of boxing or wrestling in the Temple of Tempus.
RELAXATION
Por those who don't know what to do - or who really just
wants to relax. Enhance it by letting them pick the parks,
monuments and spectacles they get to see from Volo's
Enchiridion, while they enjay some rest in Waterdeep.
RELIGIOUS SERVICE
‘There are many prominent temples In Waterdeep, where a
character can offer religious service and earn favors for later
You can find each temple in Volo's Waterdeep Enchiridion
under the ‘Castle Ward'-se
RESEARCH
Research in Waterdeep likely takes place in The Font of
Knowledge - a temple to Oghma - or other minor libraries
Specific research might take place with the aid of specialists
lUke the BlackstaffVajra Safahr or other notable figures.
SCRIBING A SPELL SCROLL
‘This one is quite simple and is also solitary work, that doesn't,
require much explanation. You can, however, use it as a way.
to get the character introduced with the Book Wyrm’s
‘Treasure and Rishaal if you want to,
SELLING A MacicaL ITEM
Run this like you'd run Buying a Magical Item - except the
other way around, of course. Introduce the character to some
of the prominent characters [rom the adventure, as described
earlier
‘TRAINING
‘This one is also fun, but keep in mind that depending on how.
Jong your downtime period is, a character might not have
‘ume to undergo training at allMAKING A PLAN
[Now that we've gone over the different aspects of the chapter,
it's time to put it all together. Create a rough outline of how
the chapter could play out. How many days should it cover?
Which factions make contact? What sidequests do you want
to putin front ofthe party?
OF course, this is simply a guideline to fellow - something
that! help you structure and manage what happens when
Like with all plans, you should be ready to alter itor discard
it in its entirety, the second your players figure something
more fun out for themselves.
PLANNING DOWNTIME
‘The downtime activities will be the main factor in
determining how many days of in-game time the party
spends between saving Floon Blagmaar atthe end of Chapter
1 and the fireball in Trollskull Alley atthe start of Chapter 3.
Trollskull Tavern. If your party wants to rebuild and run
the Trolisiull Tavern i'l Likely be the biggest me sink in the
chapter. It's a 10 or 12-day-endeavor to fix the tavern, and
running it is handled in 10-day-increments. Ifthe characters
‘want to renovate, give them atleast a month of downtime, so
‘they'll be able to fix the tavern and run it for a while.
Other Downtime Activities. If you've planned ahead,
your party have maybe informed you of the downtime
Activities they want to pursue, or have some ideas ready at,
the start of the session, Since most downtime activities can,
be divided into § or 10-day-increments, it's handy to break all,
downtime into chunks of 5 or 10 days. This saves you from
keeping close tabs on exactly how many days this or that
character have used on their downtime, while also allowing,
your faction missions and sidequests to be evenly spaced
between chunks. Use 10-day-inerements if you want the
downtime to cover more in-game time.
PLANNING SrDEQUESTS
‘While the downtime activities are the frame of this chapter,
the faction missions and sidequests act as intermissions. If
your players are interested, i's recommended that you try t
pair each character up with a faction, while giving them the
‘option to decline or go with other factions, as they wish,
Faction Missions. Most of the 2nd-level faction missions
take up only a few hours of in-game time, and can be
‘completed by a single character, Use them -and the meetings
‘ith factions agents - as small ‘breaks’ from downtime. If the
whole party isn't involved in a mission, try to resolve it
4uicidy so other players don't get bored, Remember, I's up to
you if the faction contact says "handle this mission alone’ or
‘bring your friends’ when giving the mission. Also, keep in
‘mind that some factions don't go well together.
Meeting the Neighbors. Your players will probably also
‘want to meet Lif and meet the neighbors - either by roaming,
freely or through the ‘Steel and Wood’ or "Paper Problems
sidequests. Allow them the time to do this, preferably earlier
in the chapter, so they get to know their way around
‘Teollskull Alley
Guilds and Rivals. Lastly, you have the various guild
representatives and the business rival Emmek Frewn, who
are all described at the end of Chapter 2 in the campaign
‘book and who can drop in from time to time. These represent
the more mundane challenges of running a business - use
‘them if you think your players will enjo
So HOW MUCH DOWNTIME?
Whether you think your players will love the content in this
chapter or not, 30 days of downtime is a good round number
to start with, I's enough time to repair the tavern and ran it
for two tendays, while still leaving time for other downtime
activities and a handful of sidequests. If at the end of the 30
days - the party is stil hungry for more, you can extend the
downtime as long as you like. And, if your players seem
overwhelmed, bored of aimless - oF you already know that,
they dislike downtime before going in - cut it down to 10 or
20 days.
EXAMPLE OUTLINE
Let's take a look at how Chapter 2 could be outlined.
‘We have a party consisting of a rogue, bard, wizard and
fighter. The entire party wants to rebuild the tavern. The
rogue and the bard also want to carouse and gamble, the
fighter wants to do some plt fighting and the wizard wants to
do research, as well as scribing and selling magical scrolls.
Each will also take turns tending the Trollskul Alley Tavern.
‘With a base of downtime established, we can sprinkle in
various sidequests, missions and distractions. The rogue and
the fighter are interested in working with the Zhentarim,
‘while the drow bard has been singled out by Bregan D'aerthe.
Lastly, the wizard is a good candidate for the Gray Hands.
‘They also have to deal with Lif and the neighbors who come
calling, wanting help with their various issues
‘The final outline ofthe chapter looks like this (an X noting
that a character participates in an event)
Days Rogue Fighter Bard == Wizard
Getting a
ting a x x x
15 Rebuilding Rebuilding Rebuilding Rebuilding
Steel and
eel and x x x
6-10 Rebuilding Rebuilding Rebuilding Rebuilding
Paper
Problems * x x x
VAS Gambling Fighting Gambling Bartending
Bregn x _
Diserthe
1620 Gambling Fighting Bartending Research
aes x
21-25 Carousing Bartending Carousing Scribing.
Zhentarien X. x — —
26-30 Bartending Fighting Carousing Sell Scrolls,
Of course, this doesn't mean that something only happens
every five days, or that the characters are very strict about
‘carousing or tending the bar for exactly § days at a time. I's
simply a way to alternate between rolling for downtime and,
going into actual roleplay when something happens, so you
keep a nice and varied pace. In realty, the carousing days are
probably interspersed between days of bartending, and the
factions or neighbors drop in from time-to-time during the
month,