Old School Essentials – Planescape

I have been playing Old School Essentials for about a year with four people I know from the punk scene in my city. There is one experienced role-player in the group. The others had some familiarity with D&D fantasy based on video games and pop culture.

Our first play experience was a dungeon crawl using The Pool, which gave a great sense of who they were and that we would have some preferences in common. 

After this experience, we ended up choosing to play Old School Essentials using Planescape as a backdrop.

There is a lot of ground to cover so I will try to focus on highlights and present some reflections on some things I found noteworthy or learned during preparation and play. Please ask if there are any other things you are curious about.

I think we’ve played around 30-50 sessions in total. We started with first level characters. The characters are now hovering around 6-8th level due to different experience requirements and some character deaths causing players to make new characters.


The current party and past characters:

  • A half-orc ranger
  • A paladin of the god Hoar
  • An elf (the elf character class)
  • A mutoid thief

The half-orc is the only character who survived since we began play.

There are a number of secondary characters, some noteworthy ones include:

  • A necromancer, recently killed by a beholder, now a zombie under a lich’s control
  • A fighter turned wereboar, recently killed by a beholder
  • A halfling cannibal cook
  • A gnoll captain, recruited after trying to eat the halfling cook
  • A lizardfolk priest who believes the mutoid is a god
  • A dwarven fighter

These secondary characters are played by the players and myself.


Preparing for the game was uniquely exhausting for me. My initial goal goals were to gain a basic level of comfort with Planescape (specifically Sigil) and to find a few things in the published material that made me excited about playing there. That proved a lot more difficult than I anticipated as the material is dense and I found it lifeless for my purposes of play. It is presents many of the interesting events as immutable bits of history. The last thing I wanted to do a museum tour of the setting material.

I was not really expecting the setting material to provide me with pre-packaged playable content — just something to be excited about that I could develop on my own as a starting situation. Any excitement I have about Planescape was from playing Planescape: Torment a long time ago. I really wanted to rekindle that excitement and refresh myself on the backdrop. I found a few things in the end but it took a lot of time and energy.

With Planescape, it was some of the core concepts that I found the most unproductive in terms of inspiration: factions/philosophies, plane hopping, and the kitchen sink of D&D fantasy.

There’s been no shortage of inspiration in our games in almost every other aspect. Minimizing the stuff that Planescape purports to be about has relieved the burden that I felt in the beginning.


We’re using the Old School Essentials Basic and Advanced sets.

All character classes and races are available to be played, including those from the Carcass Crawler zines. Being my first encounter with Old School Essentials, I also wanted to see how many different things played including race as class and the weirder classes/races. Necromancers and mutoids are some exotic options that have been played.

Overall, the whole experience of playing Old School Essentials has been one of experimentation and learning.

When we started the game, I had recently played The Lavender Hack by Phil Lewis. There were a few ideas I liked from my experience that I wanted to experiment with in our game. Namely, the exploration/watch system, advantage/disadvantage dice, and resource dice.

Most of these rules additions fell by the wayside as I discovered what I liked and didn’t like, what I thought worked or didn’t work. The one thing I really liked was using advantage/disadvantage dice in combat to reflected situational circumstances. We evaluate the circumstances during a given roll and decide if there should be an advantage or disadvantage.

Old School Essentials and The Lavender Hack are my only experiences with anything that brands themselves as OSR or OSR-adjacent, as nebulous as those labels are. I bring this up as a person who played AD&D and B/X in the 80s and 90s. I don’t feel much nostalgia for those experiences. Some of them were bad or forgettable, so I did genuinely wonder if I could enjoy “dungeon crawling” and a lot of the activities, procedures, and aesthetics that Old School Essentials shares with AD&D and B/X. 

Combat procedures

For combat, we are using the individual initiative rules where each character rolls a d6 to determine their order in the sequence. Ties are rolled until resolved. For the NPCs, I break them into smaller groups based on whatever logic seems right for the situation (rank, where they are standing, etc). One of the players writes down all of the initiative scores and tells us when to go.

Encounters in this game can get quite large, with 10-20 or more NPCs in the mix. This takes a long time to resolve.

For larger scale combats, I created a mass combat system that was inspired by Sorcerer. It also differentiated between named and unnamed characters. Unnamed characters were taken off the field if they lost a round, whereas named character took damage. This was fun.

Starting play

At the very beginning, we explored Sigil a bit, with specific prepared stuff in the background. I definitely prepared too much, trying to think of something in the background for every district of Sigil. This contributed to my exhaustion during prep. A lot of this prep was pretty general and somewhat atmospheric and I didn’t feel much attachment to it.

We didn’t spend a lot of time in this mode. Something happened early on the propelled everything with forward momentum. While exploring, they found a portal to a hell through a painting in a devil’s shop. They snuck through. The devil caught them on their way out. Most of the characters got out of the situation, but the devil bullied the drow character into paying the toll for using the portal with their soul.

The next session, the half-orc’s player joined the group and they decided to steal back the drow’s soul. They killed the devil, destroyed the contract, and burned down the shop. The half-orc took the devil’s finger as a trophy, which he still wears on a necklace. This was a pivotal moment in forming the party’s identity: treasure hunting trophy collectors that nobody pushes around.

Adventuring in Sigil

We’d did a lot adventuring in Sigil that developed the starting situation and positioned the characters in relation to other events, factions, and characters.

These included events such as:

  • The aforementiond devil story
  • Foiling a drow incursion into The Forest
  • Getting mixed up with a demonic crime boss named Tattershade who was betrayed to Harmonium by his wererat lieutenants in a bid for control (based on one of the few inspiring things from the setting material)

I prepared lots of dungeons during this period of play. Every one of them started with a Dyson Logos map that I liked, usually with a mix of artificial and natural features.

I experimented with many different methods: random, selected, a mix of the two, various degrees of backstory, ecology, fullness, and emptiness. I found a few techniques that worked for me. 

I didn’t find any particular method to be terrible or dysfunctional at the level of preparation. As long as I played the dungeons as “dynamic and reactive” (some words Ron used before), they played well. Sometimes I lapsed on this but it was always a good goal.

I learned to love the dungeon during this period. 

Getting out of Sigil

Eventually the characters travelled to a kind of backwater plane, removed from everything that happened in Sigil prior to this.

A place with no gods that listen. A place with powerful sorcerers ruling over disparates groups who are locked into tribal conflict over scarce resources in a hostile climate. But there wasn’t much of a social order outside of this, so the arrival of the player characters had a very displacing effect. This played very differently than when we were in Sigil, where there are many things to run afoul of.

Some noteworthy events:

  • The mutoid convincing a tribe of lizardfolk that he is their god
  • A heist on a rakshasa’s manor during a meeting of the gods
  • A mass combat with dragons, lizardfolk, gnolls, avatars, and various nomadic tribes
  • Forming an alliance with a lich

This was a nice series of sessions. My mind was less on Planescape and more on things like The Dying Earth by Jack Vance and Moon Witch, Spider King by Marlon James.

Treasure, experience, and levelling

The majority of treasure is not placed beforehand except in cases where I feel there should be something specific. After a fight, we consult the treasure table and roll on it as a group. One the players keeps track of what everybody has accumulated, and I keep track of the magic items.

I have ignored the hoard rules about awarding the treasure type based on group size. If the players defeat/outwit something, we roll on the appropriate treasure table. Due to the percentages, sometimes there is very little or no treasure.

XP for monsters isn’t divided by the number of people who earned it, each character receives the full amount from the monster listening. XP for treasure is.

At lower levels, there are a number of monsters that with decent treasure. A few good rolls made the first few XP levels easy to attain — usually after a few sessions each.

Now we’re at a plateau where we are playing many sessions for each level. We’re also at a point where we’re fighting the most powerful monsters and receiving some of the best treasure in the game, so I expect it will take longer and longer for characters to level up.

The accelerated advancement at lower levels is more generous than the text intended but I haven’t found this to be problematic in any way. Whatever the intent is, levelling up is not a big step up except at certain levels (4th, 7th, 10th). Sometimes the only thing gained during a level up was a single hit point. We’re not obsessing about it. And as mentioned above, the plateaus are real and they happen when the characters are pretty effective. In our experience, there has been a large range of play open to us at the plateau.

At some point, one player made the observation that “as our characters go up in level, we also get better at playing Old School Essentials”. This marked a big transition in how we were playing because it was at this point that they realized they didn’t have to fight everything to the death and that there were other options.

Character death

Only one player is still playing their original character. Later on, many of the players also had a secondary character. Most of those have died — and often this is because they’ve been placed closer to dangerous circumstances than the primary characters. At the same time, many of these secondary characters were beloved and we were affected when they died.

When a primary character dies, we usually call the session or the player starts making a character as the other people are playing. 

This game is not particularly generous with healing, so we are often playing with less than maximum hit points and a pervasive sense that any encounter may lead to characters dying.

One player often tells me that the game is challenging and that he appreciates that I don’t pull punches. I have thought about that a lot.

My first thought is that I didn’t play this way a few years ago. Reflecting on the Halfway Heroes Marvel Super Heroes game that was discussed on Adept Play, I think my NPCs in that game were far too agreeable and I played them too soft in combat (for example: not spending their karma). 

In this game, I really enjoy playing the monsters as monsters. I don’t think I would be off the mark in saying that many of the interesting monsters in Old School Essentials (and B/X), break the rules in some way. Beyond the basic point that they use a different stat block, they have abilities that often aren’t equivalent to abilities that the character’s possess. This has surprised me a few times when I am re-reading the stats for the monster: “Oh, they can do that?”. 

On the player side, hit points, available spells, etc can change how play occurs at any moment. On my side, a doppleganger or a jackalwere can make a lot of trouble in right circumstances. As can the physical positioning when encountering a beholder (or “eye of terror” in OSE). 

More importantly than that is that when we play this game in this way, these factors contribute to bouncy play. We’re always adapting to these and other situational constraints. Death is another variable within this, though not “merely another variable”.

Alignment and morality

There’s Lawful, Neutral, and Chaotic in Old School Essentials. We’ve been playing it more in the “cosmic” sense rather than the behavioral sense. Most of the characters are Neutral or Chaotic. The paladin worships a god of poetic vengeance.

I was talking to some of the players the recently and they came to the conclusion that their characters are evil.

This was their reflection after a year of having made many individual choices over a year of play that were sometimes noble, sometimes pragmatic, sometimes selfish, and sometimes cruel. 

They’ve always favored each other over outsiders but their group has included drow, half-orcs, lizardfolk, lycanthropes, gnolls, etc. Beyond killing creatures in the dungeon and taking their shit, the range of acceptable behavior has altered as the group has become more diverse. They often find themselves acting against those with more noble goals or who might take issue with certain members of their group based on who they are or their dietary and religious practices.

But we’re also reaching a tipping point where they are choosing to exercise their power and do bad-ass things for their own sake instead of trying to find the moral high road. These include things like aligning themselves with a lich, sacrificing humans to the fake mutoid god, flaunting trophies to enrage their enemies, etc. 

Where we’re at now

We’re still playing. We’re about to return to Sigil. They’re going back there as very different characters, with very different agendas and capabilities. I am in the process of thinking about what has transpired since they left. I am more excited to play in Sigil than I have been since the beginning. 

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5 responses to “Old School Essentials – Planescape”

  1. I’m still blinking a little at “let’s play dungeon crawls with B/X ish rules” paired with Planescape. But no justification is necessary. The twists and turns of “how shall I play D&D,” per person, are showing themselves to be endlessly odd … after all, if someone looked at me and said, what on earth are you thinking, regarding the fire-axed AD&D game I’m playing right now, I certainly wouldn’t have any justification beyond personal specifics.

    I have my own temptations about Planescape, writing up elaborate adaptations in other systems, revisiting my texts every so often, and so forth, but I’ve finally realized that it’s only about diTerlizzi’s art. About B/X, some thoughts about seeking an alleged pure experience with it show up in the discussion in Challenge and Capitulation.

    Alignment is always a tempting bunny home access point! I am dying to ask, given, yes, OK, they’re evil, but in Old School Essentials terms, are they Lawful, Neutral, or Chaotic? For the love of whoever or whatever, please don’t answer. Because “evil” isn’t an explicit consideration in OSE; yet the 3×3 alignment grid is integral to Planescape … it’s like debating the meaning of rock lyrics; it only leads to suffering.

    Systemically, I think you’ve clearly built your own thing pretty steadily throughout, including the map-based process to arrive at a dynamic and responsive situation, the full XP for defeating a foe to each participant (which I think of as a T&T thing), and the secondary character play, which reminds me of our discussion in January 2023 Q&A.

    I really like the player’s comment about getting better at play of this system/game as such. That’s something I tried to hit hard in the Free Radical course.

  2. Kind of minor question: You mention Half-Orcs, Paladins and Rangers. Does this mean you’re playing with the OSE books that back-port some of the AD&D content into the B/X inspired context? Or have you arrived at your own formulation of those things?

  3. I would love to hear more about the session with The Pool! When I first read the moment of victory rule, I thought, this would be really great for fight scenes. But I haven’t had the chance to try it out.

    • In this case, combat happened at a slightly different scale and level of detail than OSE or B/X. I did keep some of the logic about certain monster weaknesses or made it harder to kill tougher monsters. I don’t recall the monologues of victory changing things that much considering that we were already into something different with regards to ordering, effect, how much action is covered by a single roll, etc.

      I think they expanded the scope of magical effects in one or two cases compared to something in the ballpark of D&D, but most of the players didn’t have that frame of reference.

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