This document provides background information for a Planescape quest called "Main Quest: Hopeless". It includes a map of the town of Hopeless, descriptions of important NPCs like Ilmyrn the Disposable Heroine and the Gloomlord, a flowchart of the main questline, and details of quests and items. The quest involves dealing with a threat called the Gaping Maw that is trying to consume Hopeless by feeding it a willing soul, either Ilmyrn or the Bookbinder. The player must convince one of them to be sacrificed to save the town and get information from the Gloomlord on finding Ursula.

1. Main Quest: Hopeless
Planescape: Purgatorio
1

2. Table of Contents
• Map of Hopeless
• NPC Character Studies
– Ilmyrn, the Disposable Heroine
– The Bookbinder
– The Gloomlord
– The Gaping Maw
• Quest Flowchart
• Quests (detail)
• Quest items
• Conversation Trees
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3. Map
1. The Screaming Gate
2. The Chapterhouse of
the Sisterhood
3. The Defenestrated
C
Paladin (inn)
4. The Castle of Bone
(inn)
5. The Open Tomb (inn)
6. The House of the
Mayor B
7. The Well of Gloom
A
(portal to the Waste)
A. Initial position of Ilmryn
B. Position of the githyanki D
scholar
C. Githzerai beggar
D. The Bookbinder’s Shop
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4. The Disposable Heroine
Ilmyrn Ferrei is an alu-demon, the offspring of a succubus and a mortal man. She was
once a Sensate, and after deserting from the Blood War sought to experience love
in its many forms. In time, she gave herself completely to love for Aesillian, a
godling of Bytopia. He spurned her without mercy or care, and Caligstro came to
her in her anger and promised her vengeance if she would aid him in finding the
Codex. She will talk at length alternately of her love and of her hatred of Aesillian,
but will reveal nothing of Caligstro or her true purpose – to watch the PC, and
report to Caligstro on his activities. In presenting herself to the PC, she will claim
to be in Hopeless “to find one with whom I might travel to the River Lethe, that I
might bathe in it, and forget all,” - which is partially true. While she was initially
impressed with Caligstro, she has grown apprehensive of the bariaur’s ability to
deliver on his promise to help her destroy Aesillian. She will inform the PC that she
“has a considerable talent with locks, wards, and other devices and magics meant
to foil or thwart the desires and curiosity of my employer” to make herself seem
useful.
Once the Gloomlord (see pg 6) has made his offer, the PC can play on her loss to
convince her to enter the Gaping Maw, to seek the True Death.
Ilmyrn Ferrei
1 Rogue/5 Sorceress Female Spells Known: Feats: light armor, weapon finesse, weapon proficiency [simple], weapon
Tiefling proficiency [rogue], sneak attack, skill affinity (hide), skill affinity (bluff),
Str 11 0) All racial spell (darkness), infernal resistance, combat casting, practiced
Dex 15 spellcaster, trapfinding
Con 11 1) magic missile,
Skills: Bluff 2, Concentration 7, Disable Device 5, Hide 6, Listen 4, Move
Int 12 identify, summon
Silent 4, Open Lock 4, Set Trap 5, Spellcraft 4, Search 4, Spot 4
Wis 8 creature I, mage
Cha 16 armor,
Equipment: rapier [Cold Iron], belt of wasting [+1 Cha,-1 Con], bodice of
AC 12 seduction [charm person 1/d, female only], thieves’ tools +1
hp 13 2) knock, lesser 4
dispel

5. The Bookbinder
The bookbinder is a celestial who once led
the Chapterhouse of the Sisterhood. He lost
his True Name to the Gloomlord (pg 6). He
is shackled to Hopeless, now doomed to
collect and preserve knowledge on behalf of
his enemies, all the while watching the souls
of the damned pass into the Grey Waste. He
remarks that, “It is a torment worse than
being rent by the denizens of the Waste – at
least there I might find some comfort in
oblivion.”
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6. The Gloomlord
The Gloomlord declines to give his name, referring to
himself only as the “four hundred sixty-five thousandth,
one hundred eighty-second Gloomlord of the Pit of
Despair”. He states, “Names are so irrelevant, don’t you
think? I am what I am, and to call me by a name is
simply to give a name to that which I am at this moment.
Everything is mutable, changeable – nothing is
everlasting. And that is the greatest of glooms, is it not?
That in the end, no matter our stature or place, part of us
dies every moment, every day?”
A servant summons the PC to meet with him, at which
point the Gloomlord presents the PC a proposition: he
states that he knows how to find Ursula (see pg 14). If
the PC can find one soul who will give themself to the
Maw of its own free will, he will tell the PC the location of
the hag. This is not really an option: he will not permit
the PC to leave Hopeless until the threat from the Maw
has passed.
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7. The Gaping Maw
The Gaping Maw is a non-sentient entity, more a force than a
thing with desires. It is much like a virus, a spirit which
devours the will of beings in order to sustain itself in the
Grey Waste. Because it is not native to the Grey Waste, it
must continually feed or be drowned in apathy. When the
PC arrives, the Gaping Maw is starved and desperately
attempting to consume anything to prevent the loss of its
own will. Because of this, it is actually attempting to
planeshift Hopeless into the Grey Waste so that it can feed –
even though this very act would cause it to forever destroy
the gate through which its prey travels (being that it is non-
sentient, it does not understand this).
The Maw’s attempts to planeshift the Gate-Town manifest as
occasional quakes in the town and an alien voice speaking in
the party’s minds, compelling them to pass through into the
Waste. The closer they get to the Well of Gloom, the more
this voice competes with another voice, that of the Waste
itself, drowning them in a morbid ennui. This will play out as
the PC’s allies/party members begin entering a melancholy
state and falling into a listless paralysis which will require a
remove curse to lift. Until this is done the character will not
engage in combat at (script fires causing the effect of hold
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person at 20th level on the character).

8. Quest Flowchart
The Disposable Heroine can be
recruited on first meeting but may be
rebuffed in the course of conversation
options. She MUST be recruited in
order for the player to pass the wards
the githyanki scholar has placed on the
door to his room.
Options are:
1. Sacrifice her out of mercy Gloomlord is not
(+1 Good) pleased with choice,
2. Sacrifice her to preserve but reveals Ursula’s
Ilmyrn (+1 Evil) location. The PC
The Disposable has earned an
3. Sacrifice her, none of the
Heroine enemy which may
above (nothing)
play out later.
The
Bookbinder
The The
The Screaming The Petitioner The The
Defenestrated Bookbinder’s
Gate Gloomlord Sacrifice
Paladin Shop
Ilmyrn
Options are:
1.Sacrifice her out of mercy Gloomlord is pleased,
(+1 Good) and reveals Ursula’s
2.Sacrifice her, I’m not going location. Ilmyrn will
in there (+1 Evil) give player all her
3. Sacrifice her, none of the stuff if his Influence
above (nothing) check is > 5.
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9. The Screaming Gate
Outside the Gate-Town, the PC will see the Screaming Gate, so named for the appearance of the
frozen face making up its pillars. A seemingly endless procession of the Dead (not undead)
pass through the Gate, none of them noticing or responding to the PC. There is no guard at
the gate.
Once the PC passes through the Screaming Gate, he will enter Hopeless proper. An invisible
trigger line will be set across the entire street passing by the Chapterhouse so that the PC
cannot avoid it. On crossing it, if PC is good or neutral, a script will fire causing one of the
Sisters standing in the doorway to beckon him over. If he chooses to go, and assuming he
does not treat her as a prostitute hawking her wares, she will invite him in. Inside they will:
• answer general questions on about Hopeless (who is in charge, what to watch out for, etc)
• provide him with a grey sackcloth robe, which will keep the Mirthguard patrols from
accosting him. The robe has a +0 AC rating, and presents a trade-off: wear the robe, and be
attacked less by the inhabitants, don’t wear the robe, and be attacked more often
• tell the PC he is welcome to seek aid at the Chapterhouse, but they cannot aid him directly
against the Mayor or the Lords of the Grey Waste
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10. The Petitioner
PC encounters a petitioner – a githyanki who has recently jumped from a great height. His body is
obviously broken and he struggles to crawl. A trigger box surrounds him, causing a script to fire
when the PC enters it. This script causes a nearby Mirthguard patrol to accost the PC. Their captain
informs him that as the PC is a visitor, the PC must not interfere with the petitioner – his misery is
part of his penance and if he cannot stand he must crawl to the Well of Gloom to seek “absolution
in eternal loss”.
The Mirthguard captain then remarks that the petitioner’s possessions are forfeit to the gate-town’s
vaults, and that he will receive his two coppers for the Ferrymen in recompense. The captain
removes what seems to be valuables, casting aside any items he deems without value. This creates
a pile which the PC may search through once the patrol departs. In the pile the PC finds a variety of
low-value items, and the gith’s journal (see page quest items, basically it reveals the gith had been
staying in an inn in the gate-town).
The PC may choose the ultra-goody goody choice and fight the Mirthguard patrol either for not allowing
him to aid the petitioner or for confiscating the petitioner’s belongings. should It should be a
difficult fight, and will have the effect of causing all Mirthguard attack the PC on perception
(regardless of wearing the robes given by the Sisterhood).
If the PC fights the Mirthguard patrol and wins, he can loot them as well as the githyanki. The githyanki
will have the following: (insert level-appropriate gear here). If the PC does not fight and instead
only searches the pile the Mirthguard have left behind, he finds the following: (insert level-
appropriate gear here), and a strange metallic wheel with an alien script on it (his journal, see pg
15).
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11. The Defenestrated Paladin
The githyanki’s journal can be read by the following methods:
• a githzerai beggar found at C on the map (pg 2). He will be named “Gith Quipper”
and look similar to the githyanki scholar. He will require the PC pay him 5gp.
• a cleric at the Sisterhood (2 on the map). The cleric will only read if the PC is good
or neutral. Will ask the PC for a donation if good, will require 10gp if neutral.
• Ilmryn can identify it
• the PC can identify it
The journal (see pg 15) will only reveal pieces of information, the most relevant being
the author stayed “in a dilapidated hostel in the gate-town of Hopeless,” and that
his name ends in “-thaveron.” There are three inns in the town, the PC will have to
find which he stayed in to move on to the next part of the quest. The
Defenestrated Paladin is an inn relatively near the Screaming Gate; it turns out to
be the inn mentioned in the githyanki’s journal. It seems a lot of folks who stay
here end up falling from windows, not just paladins and githyanki scholars.
Anyway. The treatise ‘A Metaphorical Comparison of Planar Realities, by
T’szthaveron, First Zenarch of Kytli’ is found in the room with some minor jink,
perhaps travel-size toiletries and the like, maybe a toothbrush that doubles as a
throwing knife. The treatise has been half-eaten by cranium rats, and is scrawled
in the same alien script as his journal, on paper.
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12. The Bookbinder
As the PC passes the Bookbinder’s Shop in Hopeless, a one-time trigger fires, causing Ilmyrn to
remark that they may learn more about the scholar inside. If they ask the Bookbinder if he
has any books written by T’szthaveron, he will respond in the affirmative, giving vague
directions as to which shelf it may be found. All the books are in the Planar Common tongue,
but are not in any order whatsoever, so the PC will have to search a bit. The book the player
is looking for is called “A Brief Treatise on the Alignment System” (see pg 16). This will reveal
that the githyanki came to Hopeless to meet with Ursula the Bald, a night hag who knew of
“a book which might unlock further mysteries”.
If the player goes inside before find the githyanki’s treatise, the Bookbinder will address him in
typical Hopeless townie fashion (see conversations, pg 18).
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13. The Gloomlord
A timer begins after the PC opens the Treatise (5 minutes). On expiration, an
Ultrodaemon contacts PC by having a minion deliver a summons - he is requested
to meet with him at the House of the Mayor (6 on the map). He promises
information on how to reach Ursula if the PC will help with the Gaping Maw. The
Ultrodaemon is a pleasant enough fellow, and an intellectual, but looks pretty
scary. He informs the party that he has chosen them, being recently arriving non-
petitioners and untouched by the pervasive malaise, to aid the lords of the Grey
Waste in ensuring that the Gaping Maw is unsuccessful in its attempt to devour
Hopeless. He explains that the quakes which rock the city are not normal, but are
in fact caused by an entity known only as the Gaping Maw. The Gaping Maw
normally feeds on the will of fools who descend into the Grey Waste willingly, but
it is now starving and instead is attempting to eat that which is nearest: the gate-
town. He is not permitted to leave Hopeless, and assures the PC that he will share
the Ultrodaemon’s fate if he chooses not to aid him – all gates leaving Hopeless
are closed.
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14. Conclusion
There are two ways to deal with the Gaping Maw: feed it the Bookbinder, or feed it Ilmyrn. These
two are the only folks in Hopeless that will willfully enter oblivion.
After speaking with the Gloomlord, the next time the PC speaks with Ilmyrn an additional
conversation option will be available. If the player chooses the options carefully, this
conversation will result in the PC convincing Ilmyrn to seek oblivion in the Maw, and forget
her pain. The same can be done with the Bookbinder.
Once the PC has convinced either (or both!) to sacrifice themselves, he must go to the Gloomlord
and inform him he has a candidate. Here he will be permitted to choose which he will
sacrifice, and why. This is found in the Decision box found on the quest flowchart (pg 8). A
cutscene then shows the sacrificee stepping off into the Maw.
A perfect gentlemen, the Gloomlord then informs the PC the Ursula is in Sigil. If he is pleased
with the PC’s choice (i.e. it is not his slave, the Bookbinder) then he tells him she is in the
Hive. If not, then, he leaves it vague, and informs the PC he is no longer welcome in Hopeless
and recommends he leave immediately.
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15. Quest items
The Journal
Reveals that the petitioner is a visiting scholar, and was staying in one of the inns of the gate-town:
The top rune reads: The Working Notes of [a scratch renders the next few glyphs unreadable] –theveron, First
Zenarch of Kytli.
The individual entries:
• Day 1, Hopeless: I have arrived in the gate town, and plan to descend into the Glooms to meet with Ursula
the Bald after resting … has brought my belongings to my room …
• Day 2, Hopeless: … slept for long hours, perhaps due to weariness of the journey. No matter … the denizens
of this … curious malaise. Their pallor is of a sickly grey hue, and they are wan and … Consquently … shall
search for news of …. perhaps the hag can be easily …
• Day 3: … proximity of the Grey Waste is now palpable in my mind … forced to wake my servant … refused to
see to his duties. No matter, the effectiveness of the mindlash technique dissuaded him from further
procrastination … have found that my usual walk has had a deleterious effect upon my psyche, causing me
to rest early …
• Day 4: … has jumped from a window! He is now quite dead, and left neither …. I am now alone in this
Gate-Town. Additionally, it seems none know of where Ursula might be found, nor care of this or any
matter …
• Day 5: A voice spoke in my mind, not the voice of any being, but as a great wind – it sung to me, a song of
loss, of sorrow, of madness, of forgetting. I could not hear the final verse of the song … I know not from
whence it came, but … found myself partaking in a wine of great vigor …
• Day 6: … did not wake until … the pervasive gloom has … But I dreamed the last verse of song was revealed
… now feel a bleakness, a sadness eternal – yet one I found strangely comforting …
• Day 7: I can no longer endure this.
15

16. Quest items
The Treatise
Reveals the scholar’s name: T’szachervon, First Zenarch of Kytli
“A metaphorical comparison of planar…and so, like the fish living in a pond are unaware of other
bodies of water, most planar dwellers are unaware of other planes. As fish perceive the sky
above them, so we perceive the astral plane – a vast empty space, hostile to our bodies built
for living in this specific environment . . . bians would be the planar equivalent of those
capable of free travel between planes, holding free access to the astral. Still, amphibians can
only trav . . . ithin the confines of the island or continent on which they dwell. Like them, we
planar travelers can only travel within our own multiverse. Furthermore, there are surely
hidden planes and demi-planes within our multiverse, just as there are hidden or inaccessible
bodies of water within our own world.
…can it not be said, then, that perhaps there are other alignments and therefore other planes
associated with them?”
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17. Quest items
The Bookbinder’s Copy
A copy of the scholar’s treatise on alignments; reveals the scholar’s hope to meet with Ursula the
Bald, a hag who has knowledge of a book of ultimate knowledge:
“A critique of the alignment system: the system of alignments seems to be imposed upon reality
rather than describing it. As a descriptive tool, it is woefully lacking in power and accuracy:
(see Thorion, “Philosophical Critiques of the Planar System”) it is unable to properly treat
moral shades of grey or delineate between motivation and effect…origin of the system was
found by the Aboleth Ulchalothe (see Ulchalothe, “Encounters on the Astral Plane”) during
travels on the transitive plane when it touched the mind of the primordial called Bazim-Torag,
gleaning the secrets it learned when it ascended. The examination its brain (see Vendrin
Szass, “The Hunt of a Scholar: Harvesting the Mind of the Great Aboleth to Prove the
Hypotheses of Cosmological Creation”) provides irrefutable proof that it did indeed encounter
Bazim-Torag, and the secrets gleaned thereby were indeed valid. The being commonly
referred to as Ao developed a template for the planes prior to their creation, in this he
created the alignments as philosophical hosts for each plane. However, it seems that Ao’s
creation soon outgrew his template…in closing, I would like to state that it is my hope that my
secondary project, my search for a book rumored to describe the very makeup of the
multiverse, will reveal more…planned an expedition to the Grey Waste, to meet with the hag
Ursula the Bald, who has undertaken to reveal the location ...”
17

18. Conversation Trees
– Ilmyrn, conversation one (“Oi. Cutter. You headed into the Great Gloom?”)
– Ilmyrn, conversation two (“Changed your mind, cutter?”)
– Ilmyrn, conversation three (Door wards)
– Ilmyrn, conversation four (“Oi. Cutter. This ’ere’s a bookbinder’s shop…”)
– Ilmyrn, conversation four (Attempt to convince to go into the Maw)
– Innkeep, The Open Tomb (Lies huddled on the floor, “Leave me alone. Take any room you like.”)
– Innkeep, The Castle of Bone (“I don’t care, look in whatever barmy room you like.”)
– The Defenestrated Paladin, (will find a sign-in book with the scholar’s name in it)
– The Innkeep, Defenestrated Paladin, conversation two (I don’t suppose it really matters much if the
door is warded…)
– The Bookbinder, conversation one (Leave me to my work.)
– The Bookbinder, conversation two (I know of this scholar, yes.)
– The Bookbinder, conversation three (I would gladly sacrifice myself, that I might escape this…)
– The Gloomlord, conversation one (Summoned to speak with him, bartering for the location of Ursula
the Hag)
– The Gloomlord, converation two (Here’s your victim!)
– The Gloomlord, conversation three (Get Ursula’s location – its actually on the Prime)
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