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Planescape is one of my favorite campaign settings. It was a breath of fresh air when it came out in 1994, contradicting the more traditional Tolkien influenced ones already published. The City of Doors had a million portals leading to the Outer Planes and Prime Material Planes but also its own unique culture. Factions were determined by philosophical concepts while also being as greedy and power hungry as ones driven by bloodline or faith.
However, how to run Sigil is something that a lot of people struggle with. They get caught up in the Cant, the confusing nature of Factions, and the infinite possibilities. They struggle to figure out how to do low level games where a Balor is running the local newspaper. Where do you begin? Where do you end? Well, here's some suggestions.
1:] Planescape as Fantasy Noir and Dungeon Punk
Planescape is fundamentally unlike other Dungeons and Dragons settings and I feel that's mood more than the fact it is full of fiends as well as angels rubbing shoulders. For me, it is a place where Good vs. Evil is no longer the central premise. If I had to describe it, I would go with fantasy noir where the system is much bigger than any individual heroes. The player characters may save the Multiverse from Vecna or the Faction War but they'll still need to cover rent the next month. Ground your stories in the setting and embrace the grime of rusty swords, back alley deals, and homeless Tieflings pick-pocketing fat clerics. You can have big epic heroism but, sadly, that's a thankless job in the City of Doors.
2:] Sigil is a character
Sigil is Mos Eisley, New York, Casablanca, and Ankh Morpok rolled into one. It is a dirty, grimy, and cosmopolitan city that should be one of the worst places in the Multiverse to live if you're poor but also somewhere that most of the inhabitants would never dream of leaving. I emphasize it is a city of refugees and if you want to escape the Blood War, flee from your god, or disappear because all of the orcs on your planet have been exterminated by elves then this is the place to go. Everyone has a story and usually it involves, "Go to the absolute most neutral place in the Multiverse because no one else gives a crap."
3:] Give your players a stake in Sigil
A recommendation I have for player characters in Planescape is they shouldn't ever be full-time adventurers. Being a full-time mercenary is suicidal when you're as likely to be hired to fight Pit Fiends as well as goblins. Instead, I recommend the PCs pick and choose their jobs in-between some other profession in Sigil. Give the player characters their own inn, bar, festhall (ahem), or pawnshop to run in-between adventures. It will give them a sense they can't just uproot themselves and head off when things get bad.
4:] The Harmonium as antagonists
In most noir and punk settings, the police are useless or actively corrupt. In most D&D settings, the City Watch is more background noise. Most PCs are able to throw them around like rag dolls once they get past 1st or 2nd level. The Harmonium and other engines of "justice" like the Fraternity of Order and Mercykillers aren't like that. They go from 1st to 20th level just like PCs. However, as the elves and gnomes of Ortho found out, good intentions do not equal Lawful Good.
5:] Don't trust Alignments
One thing that Planescape was criticized for in Second Edition was that a lot of the Good aligned characters didn't act particularly good (Rowan Darkwood being Chaotic Good) and a lot of the evil monsters weren't. This is more of a feature than a bug as Sigil as the center of the Plane of Neutrality almost requires you to be willing to look past the usual stereotypes of D&D. You can be good friends with demons who are bad but loyal, angels can be manipulative psychopaths justifying everything for the greater good, and elves can be racist snooty dirtbags (oh wait, that's just how they are in 90% of D&D campaigns).
6:] Embrace the Weird
The appeal of Planescape is you can encounter virtually anything on your travels. Gigantic steampunk cities full of robot people on Mechanus, a kingdom of giant talking animals straight out of a fable, an obviously cyberpunk world ala Shadow Run or the typical "everyone good is evil and vice versa" ala DC comics? Go wild. Don't be afraid to go outside the Great Wheel cosmology either. Sigil is a place where every kind of weird sort of creature can be encountered and even if they're 1st Level Commoners, you can insert a sentient race of humanoid corgis who are all psionicists.
7:] Keep a Home Base and Recurring Cast
As mentioned in the stakes part of the suggestion list, Sigil is a place where you should keep player characters centrally located. Plenty of adventurers are wanderers in other lands but Sigil is a place where you can go anywhere and everywhere in an instant. Giving them a home base to work from is something that will help them stay invested. The PCs don't have to own the Explorers' Guild, Delivery Service, or whatnot but it certainly would help. Similarly, it's a good idea to give PCs a regular supporting cast around Sigil from neighbors to co-workers to employees. Keep a list of NPC cards or short paragraphs of local residents too if you can.
Planescape's Sigil is the kind of place where you can be shanked for the coppers in your purse. However, it's also the kind of place where you can buy the Rod of Seven Parts in a corner shop to smuggle into Poisedon's Palace to strike him down. A good inspiration is Conan the Barbarian where he was fighting alien gods one day and looting towers for jewels another. But Planescape is far more urbane and modern. Feel free to insert everything from printing presses to message-stone viewers in people's homes showing trashy plays. It is also a place where there's always a bigger fish and no one necessarily will become the kind of movers and shakers they will in other lands. Player characters should be seeking money and solving murders at level 20 as much as they are at level 1. Power in Sigil is as much represented by charisma and money than brute force.
9:] The Blood War is always there
The Blood War is an opportunity for many possible adventure hooks but the chief appeal of it is a war that can affect everything and everyone in the Planes while also having the players have no real stake in it. Like Freddy versus Jason, whoever wins, everyone else loses. As such, players can interact with it from a purely self-interested point of view or treacherous one. Player characters who might normally be above petty scheming like paladins or clerics have a vested interest in screwing over anyone they make deals with in the Blood War. Assassinations, arms trafficking, espionage, desertion, rescue missions, and other stories are all capable of being told. But in the end, the best option is for the war to carry on forever. So why not make a little money off it? Or you can, you know, try to do a little good but where's the fun in that?
10:] The Lady of Pain is just one of many mysteries
One thing to understand about Sigil is it is very old and very mysterious. How old or how mysterious is left up to the DM but it could be anywhere from tens of thousands to billions of years old. Assuming time even flows in a straight line. Things like the death of Aoskar, the Lady of Pain, her Mazes, past Factions, dead Factols, and secret locations spread through a city that has infinite pocket dimensions. Remember that the history of Sigil can be whatever the DM wants and this will make a better story to fill in the vast gaps of the past.
11:] The Factions are a never-ending source of drama
One of the cooler elements of Planescape is the fact that traditional nobility doesn't exist in Sigil. Instead, the noble houses and merchant princes are replaced by people who share vague ideological goals. These people are as prone to being as selfish, power-hungry, and scheming over petty grievances as their Clueless Prime Material counterparts. While they may and do pursue their philosophic ends, they may also seek temporal power in Sigil for no other reason than powers sake. You may also find the kind of feuding that might drive an adventure like a Bleak Cabal member wanting to humiliate a Mind's Eye member. You can easily do everything from Romeo and Juliet to Game of Thrones.
There's a certain level of cynicism to be embraced about them as well. The Harmonium want to be Lawful Good paladins who bring about an age of peace and prosperity but they're authoritarian dicks who would laugh at the concept of democracy. The Revolutionary League want to be the anarchists who overthrow the bad corrupt system but they're completely disunited in their vision of what will come next. The Free League ARE anarchists who just want to live their life free from control but that doesn't really give much support. Nobody has the right idea and a statement of belief in Sigil can mean everything or nothing.
12:] Use your words over your fists, spells, or swords
Fights should break out but PCs should be aware that they don't
necessarily know whether they can take whoever they fight so cleverness
or communication is rewarded over brawn. A local street sweeper may be a 1st level Commoner or he might be a 20th level retired adventurer or a gold dragon in disguise. This has the benefit of allowing PCs to interact with people they might normally assume they're meant to throw down with. A conversation with Glasya, Daughter of Asmodeus, is completely possible even when the goal is to rob her boudoir of her makeup kit. Rewarding clever solutions and playing politics is very true to Planescape as well as its themes.
13:] The problems of two people don't mean a hill of beans in Sigil
In Dragonlance, you can defeat the Queen of Darkness and her minions. In the Forgotten Realms, you can defeat Bane's scheme to resurrect himself. In Planescape, you may cast down the Lich Queen of the Githyanki or prevent Orcus' resurrection but there will always be another demon or monster to take its place. Individuals may be rescued and survive but a sense of existentialism pervades. In the infinity of the planes, there's always another war or god or evil plot. Keeping this mood inclines player characters to be cynical and jaded but perhaps even more devoted to recognizing little triumphs. At least in my group.
