Rules, Rulings, and the Flow of Adventure: Old School Philosophical Musings

A lot of philosophical discussions have been had about the old school style of play, but specifically here as in all posts on this blog I’ll be focusing on the basic and expert system, and specifically the OSE expansion to this system.

This should also act as a good guide to running a full session of an OSR game in the style I run in, if that’s something anyone wants to emulate.

My core philosophy is built around what I’ll be dubbing ‘the flow of adventure’. This is the general ordering and structure of an adventure, how that is impacted by the rules, and how it impacts my rulings.

I’ll clarify, that for my purposes games are generally sequential explorations starting out from a hub location: this is the genre explorative fantasy which gives context to all these blog posts, and is what I run.

So, each session is to be its own self contained adventure. I run this by thinking about the game in phases.

  1. The Pre-Travel Phase
  2. The Travel Phase
  3. The Destination Phase
  4. The Rewards Phase
  5. The Retreat Phase

Each of these phases has its own internal nuts and bolts, but understanding this breakdown should help the session run very smoothely.

The Pre-Travel Phase

In the Pre-Travel Phase, players determine their destination, figure out how they are getting there, hire retainers, and buy any equipment they might need.

Regarding equipment: they don’t need to buy every tent peg, or even tents at all. All adventuring groups carry about themselves in some fashion “General Adventuring Gear” which represents their tents and other such items any adventurer would be expected to have. The items on the equipment lists in the genre rules books feature a specific subset of items with purposes that players must prep, this includes food, water, light sources, and other significant items they may wish to pre-purchase before going out on their adventure.

The Travel Phase

The travel phase is one of the simplest parts of getting their, and breaks the entire journey down into a few quick easy rolls.

  1. Roll all the expected days of travel to check they don’t get lost, if they do, when they got lost, figure out the reprocusions of this.
  2. Roll all the expected days of travel to determine if any encounters occur. If an encounter would occur, figure out when in the day it happens (d6 beneath), and what the encounter is (d8, d12, monsters book). If the encounter doesn’t make sense, just don’t have it.
  3. Narrate the entire journey, stopping for any encounters.

The average travel day breaks into the following structure.

12 am til 6am, the morning watch
26am til 10am, the ready
310am til 2pm, the early march
42pm til 6pm, the late march
56pm til 10pm, the rest
6 10pm til 2am, the evening watch

If you need to determine who’s awake at any point in a watch, roll two people at random assuming there are 6 or more people in the group. If there are fewer than 6 people, roll someone at random.

In the ready, characters are eating breakfast, and preparing for the long 8 hour hike ahead of them, everyone is up, armouring, eating food, getting ready to journey, and packing down camp.

In the early march, the first half of the journey is covered. If you need to determine which hex the party is in in particular in the first half of their journey for an encounters just roll it.

The late march is the same as the early march, but is the back half of the journey.

The rest is like the ready, pitching tents, eating food, feeding horses, bedding down, campfire stories and general recouperation from the days hike.

The Destination

Run whatever their destination was supposed to be. A dungeon, a puzzle encounter, or whatever else.

This, or during travel encounters, is the most likely place the party will require rulings outside the bounds of the rules to be made.

As a general guide to rulings, follow the 1-in-6 philosophy. Without other circumstances or reasonable justification, the party has about a 1-in-6 chance of being able to achieve something reasonable. If the party can explain exactly how they do something, and it seems within reason, just let them succeed. If it calls into doubt their physical abilities, have whoever is leading the effort make some form of ability check.

Here’s where some of the more complex decision making comes into play. Write down a list of names of people on an adventure. If a success happens, roll a random person to determine who it happens to. Or, if you think success would be tied to competency in a particular ability score, have everybody (or all the relevant parties) roll and whoever rolls the highest while still passing is the person who succeeded (if nobody passes, that 1-in-6 just got a little bit lower arbitrarily).

Another important tool in your arsenal is the random chance d100 dice. It’s useful for “There’s a 45% chance this person is done with the parties nonsense” and “What percentage sleepy are these wolves”.

That last one is going to come in to an example I can give of all of this comign together, the worlds sleepiest wolves.

So I rolled 100% sleepy wolves. Decided they would have a 10% to wake up if a loud noise happened (remarkebly low for sleeping wolves). The party put the first batch of wolves into a magical sleep, so got them killed easily, then came the rest. Theifs took adventage of move silently to sneak in silently, then a 1-in-6 they would be quiet enough anyway (basic adventuring competency), then a 1-in-10 the wolves would wake up if they made a noise. This, if you ignore the move silently, gave about an 8% chance they woke any individual wolf while trying to kill them, while still feeling tense as they made their move silently rolls. In addition to this, I decided if the party didn’t deal enough damage for instant death then the wolves would cry out as they died, waking all the others. I let the party roll double damage (tripple for an assassin) to instakill and off the wolves without they making noise. If they didn’t overcome the wolves full HP, they’d still die anyway (adventurers are competent), but would cry out while getting their throat slit waking up all the other wolves (wolves are competent too).


Roll loot, figure out XP, hand it all out. Keep in mind the parties limited ability to carry stuff back. As a general rule, keep in mind armour, and how much slower a party will be if they are lugging at full carrying capacity (slower horses / mules, slower walking pace). Take this in mind when handling their retreat.


As with travel, but if the session is running low on time be prepared to be very liberal in ruling that an encounter doesn’t make sense for the sake of time.