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Roleplaying Tips Weekly E-Zine Issue #385

Jail Break - Part IV: Plotting and Encounter Tips


This Week's Tips Summarized 

Jail Break - Part IV: Plotting and Encounter Tips

  1. Escape Or Quest - What Kind Of Plot Are You Running?
  2. How Many Encounters Needed?
  3. Linear Or Sandbox Plot?
  4. Vary Encounter Type And Setting
  5. Ways Out Of The Cell
  6. Detail The Door
  7. Magic And Technology
  8. Don't Reward Bad Behaviour
  9. Prison Idea: Luxury Village
  10. Why Have Prisons At All?
  11. Make Your Prison Out Of Ancient Ruins
  12. Cunning Imprisonment Ideas
  13. Re-Use The Prison Experience In Later Adventures
  14. The Prison Wheel
  15. Twist: The PCs Must Break-In

Readers' Tips Summarized 

  1. Why Would The Town Guard Send PCs To Clear Out A Dungeon?
  2. Engage All Characters With Multi-Part Traps
  3. Tracking Time And Hit Points

GM Mastery: Inns, Taverns & Restaurants

The third GM Mastery book, by Johnn Four and John Simcoe, Inns, Taverns & Restaurants (PDF), is now on sale.
Click for more information at RPG Objects.

Also, during the holiday season, pick up
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Or grab the GM Mastery Complete Bundle at RPG Objects

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A Brief Word From Johnn 

Happy Holidays. Next Issue Week Of January 14

I hope you have a safe, fun, and game-filled holiday season this year. The next issue of Roleplaying Tips will be the week of January 14, 2008.

Movie List Coming Along - Could Use More Entries

Thanks for the movie entries to date. I'm putting the information together and will have it ready for you in 2008. :) The list is a bit short, so any ideas you have on what movies GMs should watch and why would be great.

Volume 6: 5 Room Dungeons Ready For Download

The sixth volume of 5 Room Dungeons contest entries is now ready for download. Featured in this volume:

  1. Diamonds and the Deluge by valadaar
  2. Bedizen's Traveling Dungeon by Scrasamax
  3. Thieves' Guild by Aki Halme
  4. 'Ringed' by fadeaway1978
  5. Tomb of a Cleric by Uri Lifshitz

Download (PDF 1.2 MB)

My New Book Is Out In PDF Format

If you liked NPC Essentials, you'll also get great value out of GM Mastery: Inns, Taverns & Restaurants. It's full of unique design tips and ideas, plus tons of plot hooks and encounter seeds. It also has several generators and tables, including a random menu generator, 10,000 random names for inns, taverns, and restaurants, and more.

The ad above has links to a GM Mastery holiday sale, or click here for direct info about Inns, Taverns, and Restaurants.


Johnn Four,

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Jail Break - Part IV: Plotting and Encounter Tips  

by Johnn Four

1. Escape Or Quest - What Kind Of Plot Are You Running? 

Before playing any prison adventure or encounter, first decide what plot you're running. It's a quick decision to make, and helps focus design and GMing. It's important to be clear on what you are doing, and to match player expectation with yours.

Most prison plots split into two groups:

  1. Escape
  2. Quest

1) Escape

Imagine if you have a quest plot planned, and the group is intent on gaming out an escape plot. Players don't like their characters controlled by outside influences, and most will try to escape a controlling situation, such as prison, at the first opportunity. It's upsetting when everyone misses your plot hooks, clues, and NPC interactions because they're so focused on finding the quickest way out.

An irony of escape plots is they often require PCs to break the law to gain freedom. Think about how the prison escape will affect the future of your campaign. If you don't want the PCs branded as criminals and hunted, design one or more ways for them to be cleared of charges, immune to prosecution, or excused of their conviction and prison sentence. In addition, escape must not add more criminal offences to their record.

  • A powerful NPC uses his influence to clear the PCs' names in exchange for a favour.... A nice twist if it's the villain who does this.
  • The PCs perform a good act, which sways public opinion.
  • The PCs might be able to break into the local records office and forge their files.
  • The PCs can pay high rates (perhaps requiring more jobs or quests) for the best legal trickster in town.
  • You offer the opportunity for the PCs to frame a villain or rival for their crimes.

2) Quest

The PCs are in prison to achieve a specific purpose. Escape might be guaranteed as part of the mission, or is an end- challenge to be met once the primary goal is accomplished.

If the quest is assigned after capture, ensure you introduce it as quickly as possible so the group doesn't get fixated on breaking out. You will also need to provide a hook that's stronger than the players' desire to be free of their shackles.

  • Find a missing NPC whose identity must be kept secret from the other inmates.
  • Get face-to-face time with a gang leader to secure the safety or good standing of an NPC who's on the outside.
  • Learn the source of undead inmates being unleashed within the prison's walls at night.
  • Trick or force a demon inmate into revealing the secret location of his horde of souls.

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2. How Many Encounters Needed? 

Once you've figured out the plot goal, you should scope out plot length. Are you planning for one encounter or several?

A one encounter plot is simple. The PCs are in jail and the means of escape or the quest goal is easily at hand. There might be a nearby secret door to find, allies might intervene, an NPC interaction queues up immediately in the cell the PCs occupy, and so on.

Staging multiple encounters requires more planning. Consider each encounter trigger carefully and try to make it foolproof. Prison often means PCs have restricted movement, limited access, and reduced interaction. If the PCs earn punishments, their options might be shaved away even further. Ensure your planned encounters won't get bypassed or made impossible because characters can't get to them, or have eliminated the path or trigger condition.


  • NPCs: Important NPC is attacked or insulted. The PCs decide to side with an enemy or rival gang.
  • Location: The PCs can't reach the location because of aggressive guard placement, lack of prisoner access, difficult alarm or defense systems.
  • Punishment: PCs attack or abuse guards, are caught breaking the rules, or stir up other prisoners. Punishment is normally segregation, (such as solitary confinement), increased surveillance, or added security or restraints. Be careful how you punish PCs in terms of future encounter possibilities.
  • Equipment: Reduced equipment might render some character abilities useless or too limited to wield.

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3. Linear Or Sandbox Plot? 

Are you providing a sandbox where the PCs are free to roam and tackle things at their own pace, or do you have a specific timeline and plot in mind?

It's easier, and perhaps more tempting, to run a linear prison plot than with other setting types because the PCs' are more controlled. Agreed, some prison settings are little more than a secure, common area. But for most prisons, the PCs' daily life will be dictated by the administration. There are set times the PCs can eat, be outside, socialize, and access certain areas. All other times the PCs must be in their cells.

Other adventure control levers:

  • Lockdown. Without notice the alarms sound and PCs are ordered back into their cells. Use this to end encounters abruptly. Lockdown is not a good stalling tactic though, because without interaction, time passes quickly, and you'll be expected to serve up a new encounter or let the PCs out soon.
  • Roommates. You determine what NPCs are nearby or share a cell with the PCs. This helps you provide important communication channels through contacts, give clues based on NPC knowledge, add skills the party might be missing, or generate instant enemies and conflicts.
  • Social structure. Factions are constrained by space and prison population size. It's easier to create a world of intrigue, rivalries, and conflict because the setting has such a tight scope.
  • Map. The map controls security and freedom of movement. For example, brightly lit areas prevent shadowy dealings.
  • Security. You can increase or decrease security to make areas more or less attractive as options for the PCs. For example, if a meeting place is required, you can make a certain hallway at a certain time vacant due to a gap in patrols, or you can create surveillance blind spots that guards haven't discovered or dealt with yet.
  • NPCs. NPCs are easy to add or remove in prison. Plus, information travels fast, so you can provide new or misleading information at any time without stretching disbelief.

If you expect the PCs to explore the situation and their options, you might be disappointed. Prison to them might mean waiting for the GM to dish out the plot. If you have sandbox play in mind, then before you get frustrated by a passive group, have a quick chat with them out of character - or in-character with a wise NPC - to discuss play style.

If you have a plot or timeline in mind, put yourself in your players' seats for a minute. What would they do? What actions would they likely take? Plan for this in addition to GM wants and ideas.

For example, you might have a vision of prison being an exotic dungeon environment with a tense plot that builds up to a prisoner riot, which will give the PCs their opportunity for escape. However, don't be surprised when players focus entirely on the structure of their cell and try to puzzle out for hours how to escape. They might resent being imprisoned and want to get out immediately, whereas you see it as an adventure setting and assume the PCs will spend time exploring its possibilities.

Be clear in your mind what type of plot you've got planned - linear or sandbox - and watch for signs your group is expecting and gaming something different.

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4. Vary Encounter Type And Setting 

Prison encounters, due to their constraints, can get dull and repetitive. For each encounter you have planned or that results from character actions, stop for a moment and consider your options. What kind of gameplay are you after? What could make this encounter even more interesting?

First, vary your encounter types:

  • Action or combat
    • Fight with prisoners
    • Fight with guards
    • Combat with elite guards or special ops
    • Fight with visitors if contact is possible
    • Combat with unexpected foes, such as monsters
    • Chase
    • A physical contest or trial
  • Puzzle
    • How to escape cell
    • How to escape facility
    • Survival - PCs have no resources and must invent equipment
  • Roleplaying
    • Gather information
    • Gain influence
    • Earn respect or reputation
    • Make key friendships
    • Negotiate for resources
  • Skill use
  • Access secure areas
  • Deceive guards or other inmates
  • Games of skill or chance
  • Leverage available resources

Next, try to vary encounter settings:

  • Medical exam room
  • Surgery area
  • Medical recovery ward
  • Large cell
  • Small cell
  • Large cell converted to any purpose
  • Stairwell
  • Cafeteria
  • Secret room through hole in the wall
  • Furnace room
  • Engineering area
  • Basement area
  • Warden's office
  • Guard tower
  • Gym or exercise yard
  • Surveillance room
  • Visitor secure room
  • Washroom, showers
  • Workshop
  • Library
  • Chapel
  • Guard change room
  • Staff lounge
  • Sports field
  • Quarry, mine
  • Farm area, field, garden
  • Tool shed
  • Kitchen
  • Sewage, garbage, waste area

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5. Ways Out Of The Cell 

If your prison situation involves a cell, holding pen, or some other confined space, likely the first thing to occur will be the PCs looking for ways to escape. Be prepared to answer the typical questions players will shoot at you, and also decide how difficult it is to escape from cells ahead of time. This seems obvious, but I can remember several times having to pause and think about this in-game when asked, and then being caught in reaction mode for the rest of the escape adventure.

Here's a list of ideas on ways out of a cell. If the PCs wind up in prison more than once, it helps to keep things interesting by switching up escape routes:

  • Secret door
    • Walls
    • Floor
    • Ceiling
    • Magic
  • Tunnel
    • Dug by PCs
    • Dug by previous inmates
    • Loose brick or stone
    • Compartment or space behind it. What's inside?
    • Hole: allows reach to outside door lock
    • Hole: allows reach into hallway or adjoining cell
    • Weakens wall, floor, or ceiling
  • Get key off guards
    • Bribery
    • Force
    • Trick
  • Lockpicking
  • Bend bars, lift gates. :)
  • Recruited - other prisoners already have plan
  • Legal - Appeals
  • NPCs who know the way out
    • Blackmail
    • Deal-making
    • Trick
    • Threat
  • Outside help
    • Friends tie ropes to bars and pull wall down with horses
    • Allies disguise and infiltrate
  • Unusual, magic, or esoteric
    • Strange acid bugs used to corrode bars
    • Ocean spray has corroded pipes
    • Shapeshifter recruited to help

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6. Detail The Door 

Pay attention to the door or entrance, as it always gets a thorough examination from the PCs as a means of escape. If you haven't thought things through, you'll end up improvising yourself into a corner where the PCs escape too easily, or you become inflexible and give off a "no" vibe that frustrates players.

Here are some door elements to ponder when you have a few spare moments before the game:

  • Hinges
  • Lock
  • Material of door
  • Construction quality
  • Frame material and construction
  • Door fit - gaps around edges or at bottom?
  • Walls near door - material, quality
  • Ceiling over door - material, quality
  • Floor before and under door - material, quality
  • Window? Barred or shuttered?
  • Peep hole?
  • Food tray or access hole?

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7. Magic And Technology 

Magic and tech pose big problems for prison guards and administrators. If such things are common and accessible, it might not even be worth it for a society to have jails. If it's rare, then there might be special prisons, unusual sentences, or specialized cells. For example, mages with teleports might be put into a coma for their sentence, or have the means of spell casting removed or nullified.

First step is to make a list of the PCs' extraordinary abilities that would affect your prison adventure. If your plot is to escape, then ask yourself how each ability could short circuit your plans. If your plot is a quest, then escape isn't a huge factor, so just look at abilities in terms of your encounter plans. Best case scenario is you craft situations that put PC abilities into the spotlight, and which reward creative thinking.

Next step is to determine how prison designers and staff would react to special technology and abilities. Are these inmate advantages known factors? If so, steps would be taken to deal with them. If not, then the PCs can operate with greater freedom, as security would not specifically target those advantages.

Here are a couple of GM-killer categories than can end planned adventures far too soon if you haven't given them some thought:

  • Movement. Spells, such as teleport and blink, can easily bypass walls, patrols, and defenses, as can technology such as transporters and teleporters. Special abilities that allow flight or super jumping are problematic if prisoners can get outside.
  • Communication. Prisoners who can communicate with each other can pool resources, even if it's only ideas and planning. Communication with outside agencies lets strategic information pass back and forth.
  • Ability enhancers. Prison specs will cater to average or above average inmate capabilities. If the PCs have ways to give themselves super powers, then prison constraints might be inadequate.
  • Material manipulation. Can the PCs make walls soft, or disappear altogether? Can they fabricate powerful weapons on the spot? Check for any kind of material manipulation ability and think how the PCs might use it.
  • Buffs or threat reduction. A PC with immunity to physical damage will just walk out the front gate and ignore the bullets shot at him. Likewise, temporary boons that let PCs easily overpower or capture guards makes them a threat to security, and possibly your plans.

Potential solutions:

  • Read problematic spell descriptions and spell rules carefully to look for ways to prevent such spells from working, to leverage limitations, or preferably, to inspire interesting puzzles and challenges for players.
  • Look at technology's limitations, such as needing to get a lock on the target, power sources, or line of site.
  • Look for counter technologies that knock out, dampen, or attack the PCs' tech.
  • Install superior surveillance and have very fast response times. Unusual PC behaviour is immediately spotted and acted upon. Perhaps a fast-acting gas pours into the cell, or guards are only 3 seconds away.
  • Use special materials immune to hi-tech or magical manipulation. To make a game of it, give the material a special weakness that PCs might be able to figure out.
  • Place the prison in a secret location. This might prevent movement technologies from getting a lock on the PCs, or prevent PCs from getting their bearings.
  • Place the prison in a deadly atmosphere or environment. If anyone does escape, they won't last long without protection or precautions.
  • Look through your lists of spells with permanent or long- lasting effects. Curse, blindness, and deafness, for example, might be cast on problematic inmates.
  • Look to cursed magic items for ways to limit powerful inmates.
  • Monsters, aliens, and creatures might have special abilities to add security or challenges. Certain dogs, as a simple example, use scent to track down escaped prisoners on foot with high accuracy. Imagine what's possible if you add magic, psionics, and alien tech into the mix.

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8. Don't Reward Bad Behaviour 

If a PC commits in-game actions that are ruining the fun, not respecting the game, or obviously against the law, by all means throw them in jail. However, don't then reward them with special in-jail scenes. This gives the player spotlight time, a private adventure, possible experience and treasure, and worst, a reward for their bad behaviour.

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9. Prison Idea: Luxury Village 

From: Gus

A local baron came up with this idea for adventurers - usually groups of powerful men, so it was hard to prevent them from escaping: Luxury Village.

Here, the adventurers are well-fed and entertained. All had to promise not to attempt to escape and have to leave a deposit guaranteeing their stay.

Of course, there's an upkeep tax to be paid for all the luxuries, wine, and fine food while they stay here, but prisoners have been so happy with the attention received that some even commit minor crimes to be allowed to stay there.

This is a great boon to the local economy. While some citizens don't like the lack of punishment, they are happy that the adventurers are not causing trouble.

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10. Why Have Prisons At All? 

From: Garry Stahl

The Eyrian Empire of my Thindacarulle setting does not have prisons. Jails are places where you are held until trial (clean and bare), but there are no prisons. Punishment is either fines, corporal, capital, or slavery. Convicted criminals are bonded from periods of 90 days to life as slaves - slaves with a pretty good set of rights, but slaves none the less. Difficult criminals end up polymorphed into useful beasts of high intelligence.

One notable jail, where the constable is a black dragon, is a doorless stone box with narrow windows. The dragon gets you in and out by lifting the multi-ton stone roof.

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11. Make Your Prison Out Of Ancient Ruins 

From: Tyler Elkink

FFXII used, with great effect, the idea of a prison made out of ancient ruins. The applications of the idea to a pen-and- paper game are many, but one in particular struck me.

Johnn, you mentioned the possibility of prisons as a campaign setting, which got me to thinking about the application of ruins. Ideally, the prison has a one-way gate, and the prison is a self-contained world. You have a healer, food supplied from the government, local thug boss leaders, etc. But there's a crypt, or temple, or maze, on which the prison is based. Rather than spend thousands of gold, why not just slap a gate on the front door of that old ruin you're not using? Nobody ever escapes the ruins, after all.

Thus, the adventuring party has plenty of space to explore. Eventually, they might escape the maze, arm the prisoners, lead an uprising, find enough treasure to bribe the guards to let them out, etc.

"Home base" still offers plenty of roleplaying opportunities, and an easy way to throttle the acquisition of spells, items, or equipment. The PCs might unwittingly defend an evil kingdom from cthuloid horrors plotting to eat the prisoners and burst forth over the land. Why would the guards believe the prisoners' warnings about danger below, after all?

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12. Cunning Imprisonment Ideas 

From: Bobby Nichols

To coin a phrase, "Four walls and a ceiling do not a prison make."

  1. Pocket dimension.
  2. Permanent feeblemind.
  3. The imprisonment spell.
  4. A three dimensional maze. (Prisoners are told there is a way out before they are teleported to the center. Of course, the person doing the imprisoning is lying.)
  5. Polymorphed into a hated creature.
  6. Permanent gaseous form.
  7. Polymorphed into a plant. (And he's decorative too! And in the autumn his apples feed the community.)
  8. Encasing a person's head and hands in iron (e.g the man in the iron mask without eyeholes).
  9. Dismemberment (ick).
  10. There was an old Ravenloft module where the PCs wake up as brains in jars. The bad guy returns them to their bodies or someone else's bodies in return for a favor.
  11. Permanent reversed comprehend languages (so no one can understand what the person is saying).

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13. Re-Use The Prison Experience In Later Adventures 

From: Justin Stranack

Hi Johnn,

I thought I might share my take on some of the potential that a prison break can have over a far-reaching period of time. Perhaps the PCs are locked up for one of many numerous possible reasons, such as the rogue I DMed who thought it would be a good idea to pickpocket the priest who raised him back from the dead. That landed him in jail, as well as his friends, who later tried and failed to break him out.

At the time, the potential of a prison scenario eluded me, but having had ample time to brood on it, I think it could be quite fun. Perhaps there is a design flaw in the prison, or it was unfinished for some reason and the original designers were unaware of this. Regardless, the PCs find a way out.

Later in the campaign, the city itself is placed under heavy guard, but the PCs need to get back inside. If any of them should remember the prison flaw, this could make for an interesting scenario, breaking back into the very prison they escaped from sometime earlier.

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14. The Prison Wheel 

From: Rekres

There was one Dungeon adventure module that featured a rather usual prison. The whole thing was a giant stone wheel enclosed in the heart of a mountain. There were 365 cells (one for each day of the year). Once per day, all of the prisoners would push, rotating the wheel one notch, which would align one cell with the opening. This allowed the guards to release one prisoner and install a new one.

The scenario was all about the PCs finding a way to circumvent the prison and release a rebel leader who was needed elsewhere. Brute force wouldn't work because the party could hack its way into the complex, but the cells were all stone and sealed off except for a slot in the top to allow food and in the bottom so prisoners could push against the base. Possible methods were potions of gaseous form and acquiring an earth elemental (or other burrowing creature).

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15. Twist: The PCs Must Break-In 

From: Gary Williams

This might seem like an obvious idea, but a great adventure hook is to have the characters break into a prison, perhaps for information, for an item, or to rescue a specific prisoner. This allows the characters to collect information about it before going in, and sets an interesting stage. To make it more difficult, have all the prisoners chained, hooded, and gagged, so there is no easy way to tell one from another.

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Readers' Tips Of The Week: 

Have some GM advice you'd like to share? E-mail it to - thanks!

1. Why Would The Town Guard Send PCs To Clear Out A Dungeon? 

From: James B Ross

re: Roleplaying Tips Issue #384

The question of why a town guard would send a group of adventurers into a dungeon, rather than taking the job on themselves, was raised in a recent Reader Tip. The answers provided were very good, but I think there are additional compelling reasons.

First, the job might be too easy, too hard, or too unimportant for the local militia. A small payment in the hands of the PCs could be a good investment, and a great reason for the PCs to get jobs.

Second, the militia often discover the best way to deal with adventurers is to employ them before they get bored. Pay them, send them off, and with any luck they will either come back as heroes or not come back at all. If they come back as heroes, the mayor gets to take credit for hiring them; if they don't come back, at least they won't be causing any trouble.

This creates several possible plot points:

  1. An enemy might have paid officials to get rid of the PCs by sending them on missions they are not prepared for.
    1. The nature of the mission might be mis-stated. Instead of a vampire, the PCs are facing werewolves, for example.
    2. The mission might be trumped up. The enemy has stated there is a lady captured by the local bandits, when the lady is actually the bandit leader, or perhaps long dead.
    3. Multiple crews of adventurers could have been commissioned with the same bounty. The others could have been encouraged to elbow the PCs out of the way.
    4. When the adventurers begin to form an odd habit of surviving, the officials begin to get nervous, with even more ominous results. Perhaps the militia will begin to set specific traps, or even personally attack the PCs. The town guard might well have better contacts and begin to place rumors causing crucial townfolk to turn against the PCs. Openly attacking the town guard will certainly earn them enmity and possibly a lynching.
    5. The missions could be designed to arouse the ire of a powerful enemy.
  2. The local officials might begin to covet the PCs' rewards - either their fame or more tangible rewards that lay in dungeons. All of the above treachery could be employed. Furthermore, officials might send the PCs to soften up specific targets so their men can snatch the real reward.

    Politicians don't have as many different skills. Often, their only skill is guile, and their only task is treachery. These officials should be played as if they know what they are doing.

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2. Engage All Characters With Multi-Part Traps 

From: Tyler Elkink

I recently struck onto a solution for "thieves go off to open locks while the party waits" problem: multi-part traps. If it's a thief and his non-thief friends, the trap might involve unlocking or disarming something while, say, making concentration rolls to channel magic into a battery, or balancing a weight, or holding a large stone lever off the ground, or some other simple but combined use of class skills or high stats.

If it's just thieves in the party, then multi-part locks or traps, where they have to be disabled at the same time, ensures the party lives or dies together.

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3. Tracking Time And Hit Points 

From: Willem van Driel

In my games, to track time, I use printed sheets with point- bars like this:

1. ooooo-ooooo-ooooo-ooooo-oooo
2. ooooo-ooooo-ooooo-ooooo-oooo
3. ooooo-ooooo-ooooo-ooooo-oooo

During play, I cross off boxes to mark the time my players have spent doing something. You can add notes to the bars to indicate planned events, dawn and sunset, weather conditions, etc.

With the copy/paste function, you can quickly make as many of these bars as you need, and most word-processors have a function that will automatically number each line for you.

I use the same system for hit points. It speeds up play because it removes the need to calculate and write down the remaining hit points after every hit. It also allows you to see at a glance what state NPCs or monsters are in.

Hope this helps.

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