5 steps to make great D&D Prison breaks

D&D prison breaks

D&D prison breaks can be the central focus of a campaign. They also can be a side mission but most dungeon masters want to pull off at least one prison break in their career.

D&D prison breaks have a simple formula to follow. Plan, make happen, escape, live while being chased and then forget about it unless you read this post.

We will first go over the steps of how to make a great D&D prison break and then go into eventually how this will impact the rest of the campaign.

The 5 steps of a prison break

In order to make a prison break happen you need to follow a 5 steps.

  1. Figure out why they are in prison.
  2. Plan the escape.
  3. Escape!
  4. Survive and evade.
  5. Live with the consequences.

Only 5 steps to follow but there is a lot that goes into each step.

Before we go into each step, if you are wondering how to arrest players we have an entire article dedicated to it here.

Before you even go into these steps you should make sure that the players know each other. If they are a group of convicts who got together to form a group figure out why they would work together. They do not need to necessarily have bonds of loyalty but they should have a reason why they are breaking out with these people.

You also need to determine how long these people have been in prison. If a person has been in prison longer they will know the place far more intimately than a newcomer would. This can also lead to a lot of extraneous factors later on in the campaign once they escape. That is if you are playing past that point.

Once you have figured out how they are going to work together and why you need to determine why they are in prison.

The sentence

Were these people heinous murderers who were justly sentenced to life in prison? Were they people who were locked up for drug use or some other misdemeanor? You need to answer these questions.

If the players were all locked up for murder it will affect their characters and the facility in which they reside. The security will be tighter and there will be more precautions. This is also the same for political imprisonments or when a high figure of authority wants someone locked up.

On the other hand, you have small misdemeanor crimes. These prisons are your typical types of prisons that do not lock up violent criminals. They, therefore, don’t need as much security and the security that they do have should be lax.

Most first time offenders will be in these types of prisons. This is where most parties end up. With lax security and incompetent guards even though they can kill an elephant in hand to hand combat.

The sentence for your players will dictate the security of the prison and that is very important for the rest of the prison break.

Planning the escape

The amount of planning depends on the level of the characters and the severity of the sentence.

If your players are in prison for murder or other heinous crimes they will have an almost impossible time getting out of prison. These are also the prison breaks that movies are made out of so you might enjoy these prison breaks more.

If your players are in for small crimes you might not even need to plan the escape. They may just bust out and walk away. The other steps and consequences will still apply but this phase won’t be as hard.

Planning can be an in-depth part of your game that takes sessions to gather the appropriate information and set up or it can take 5 minutes. That depends on your setting.

For more in-depth planning you need a bigger and more secure facility.


Prisons with tight security can’t just let you pick a lock and escape. There are multiple guards, the area is big, and there are possibly multiple hurdles to overcome.

Your players might need to get a magical key card to get through certain areas and there might teleporters to confuse them.

Magic adds a whole extra level to a prison break for the extremely dangerous and capable. Can players use magic? If so what magic and why? Why can players not use magic if there are restrictions and how do they work?

You will need to answer all of these questions about magic first and then plan your prison. There is nothing worse than planning an awesome prison in real life to only have your players cast sleep and knock continuously on high-security doors.

Are Keys magically enchanted to only allow a certain person open it or are your players able to use them once they are acquired?

There are a lot of extra things that you can add into D&D prison breaks that differ from normal prison breaks. You just need to make sure it is challenging, but not impossible.

A good rule is what I call for myself the 3 possibility rule.

If you can think of 3 possible ways that your players can beat a scenario then they should be able to figure it out. On the other hand, you could have very capable players looking for a challenge. For these players, you don’t need to know how to win. Good players will continually surprise dungeon masters and win in an unwinnable situation.

Be careful to accurately judge your players’ capability. If they are not experienced players who like challenges go with the 3 step rule. Unless you have successfully pulled off one of these situations with your players follow the 3 step rule until they repeatedly impress you.

You also have to consider prison life.

Prison life

In our world, we have prisoners work. Does your world force prisoners to work as well? If so this presents a lot of different opportunities. You can have prisoners learn about the prison and gain a bunch of different resources that were otherwise inaccessible to them.

You can skip past the boring parts but make sure for the first day or two that the players go through everything. Tell them their schedules, what people do, and give them enough information to work with.

After the first day or 2, you can skip the boring stuff. Only tell the players what is different from day to day. If your players are stuck you can add new variables like a new guard, prisoner, etc. New possibilities mean hope.

Most television shows make our prison guards seem like they go on a power trip and beat the prisoners. This is based on the Stanford prison experiment and is completely false. Most guards do not have a power trip against normal inmates. If you want to make your world that way you can as well to add some villains into the mix, but you should also add some allies.

Your players are not the only ones wanting to get out. You can give them NPC allies that either wants to escape with your group or just give them supplies. This provides interactions that let you give even more options. If you want to learn about NPCs read this article.

At the end of the day, more options and information is a good thing. You do not want your players to hopelessly complain about how it is impossible to break out. You want them to think and make this prison break work!

Most D&D prison breaks skip this portion, but you can make it last for quite a few sessions and be extremely interesting. Now onto the main part that everyone thinks of.

The escape!

I have seen D&D prison breaks handwave the first 2 steps and it has made them less exciting. I have however never seen anyone ignore the 3rd step and that is the escape!

The escape is the most exciting part about D&D prison breaks. You have tension, rolls, natural content that makes it easy for most dungeon masters to work with.

The players do something to escape. This could be breaking down a door, a carefully made plan, or anything in-between. If the escape is planned out you shouldn’t just ignore this section. There should still be some thrilling aspects.

Do you need to roll in an escape?

The answer is yes.

You cannot just pre-plan everything and have it go according to plan. Something might happen. A disguise could be off, a barbarian didn’t eat enough and therefore rolled a 1 on breaking the prison bars, something can happen.

I would suggest to not allow too many rolls. Rolling gives your players a chance of failure. Rolls are meant to give a sense of tensions since failure is possible. Because failure is possible you should not make your players chance failure over and over again.

In fact, you can try to warn them about failure. When asking about their plan you should make sure that you understand what they are going to do. If there is a decent chance of failure or really any at all you should ask about the backup plan.

P: “We are going to do x and get out!”

DM: “Okay, so you are going to do x and if something happens then what?”

Be clear that you understand their intentions so that there is no “well actually” moments. You can also subtly inform that player that they might want a backup, or you are just asking in case something doesn’t go according to plan.

You have made sure that you understand them and now it is time for the escape!


The climax of D&D prison breaks is the escape. Everyone has a plan, but no plan survives contact with the enemy.

The plan can be simple or complex but something needs to happen.

If your players plan and roll perfectly narrate it. Talk about the flustered guards, how their accomplices are doing what they need to, and do so with energy. This is an exciting time so you need to show it.

If the players are failing, make it a mad scramble. Something else might go wrong in the prison so provide at least 1 other opportunity that the other inmates have created. A riot might be a distraction that lets your players escape into the sewers. Give them something to work with.

If your players end up failing in their escape that is okay. It happens. They will be put under heavier security but they will have also learned more about the prison. Most D&D prison breaks don’t end in failure though.

Your players are incredibly resourceful. Most of the time they will not fail in escaping from prison so don’t worry too much about it.

The action part should be relatively fast-paced and follow the planning steps. If it is improvised everything will be messy. Just have notes on what you need and the escape will be fine.

But what happens after you escape?


This is sometimes glossed over for misdemeanor prisons but for major prisons, the chase is very important.

The players will be hunted with dogs, familiars, magical beasts, and everything that the prison has at its disposal. If the players did their research well they will have learned about these measures and take precautions against them. Most of the time players never bother to learn about what will be chasing them.

Here you can have fun with a lot of different monsters and classes but I would recommend against making anything special. We as dungeon masters do not want our players to lose. We can make D&D prison breaks almost impossible to escape from with a variety of monsters but that isn’t fun.

If you are going to use flying creatures only use the for tensions and make the DC to escape a bit higher. This way the party knows they are being tracked and have to keep moving since there is only a limited amount of time before they are caught.

The players will have to keep running for quite a while in order to completely evade their pursuers and most of the time the prison guards will not just give up.

If the prison loses prisoners what is their future like? Their reputation is on the line so they will pursue the party for a long time unless the party is a high level in a minimal security prison.

They should always be watching their backs, trying to cover up their trail, and never get a full night’s rest for a week or 2 if they are lucky.


The 2nd part of the 4th step is survival. Some dungeon masters handwave this away but others want to make it a deciding factor for the party. Being chased and constantly on the run trying to survive can make for an exciting adventure but there are some things to consider.


Magic can make your survival aspect of a prison break negligible. I have had many survival instances solved even in first edition with the creat water spell. Now all you need to find is food and food is not as necessary was water. Speaking of food there is a spell that pretty much has you covered. This video explains it pretty well.

There is weather and hunting as mentioned in the video but food and water are an issue for survival. Hunting is a bit of action and weather is a challenge to overcome. None are going to kill the characters (usually) and you need to make the game be a bit more interesting.

Once you home rule magic or do something about potential spells like goodberry you can begin the survival aspect.

The players will need shelter, food, water, and rest.

They need all of these things while being pursued and it might be difficult to do all of them.

Think of this like a simulator where you plan out your time. You spend x hours eating, resting, gathering food, and possibly dealing with unexpected encounters. All of these need to be scheduled, but if you spend too much time on them instead of running it will be game over.

You should also try to consider tools, what they have, and any gain in items like a flask is almost the same as a magical weapon to your players.

Survival isn’t covered the best in the normal D&D rules, and it is hard to find good information on it. After looking for a while I was able to find some tools, survival rules, and more. You can find survival puzzles and more at our affiliates Dungeon Vault. They have some helpful materials like survival puzzles that you might find useful.

But what if your players escape, survive, and getaway?

Living as convicts.

This is the part most dungeon masters forget about. The players escaped and are just pardoned or it never comes up that they were in prison. This is not realistic.

If your players escaped prison instead of serving their time they were not pardoned or asked to a job to eliminate their sentence. They ran away and broke the law.

You should always have this be a focal point of your game.

Are they hunted by bounty hunters? Are there wanted posters of them in towns and cities? Do players have to avoid towns and cities or risk being taken back to prison? Can this be used as blackmail on the player? There are so many things to consider.

This black mark on their record should be prominent in your campaign and never forgotten about completely.

They can do other things but this part of their history should stay with them and enhance the game.

Speaking of continuing the game.

Objectives after the break

What do your players want to do after they break out of prison?

You need to think of some objective to make the campaign continue on. The players have already formed a group that probably should stick together so give them something to do. Appeal to their criminal background and give them a mystery that could get them money. Let them know that employment will be difficult as well.

You don’t want them to return to their daily lives unless the campaign was meant to be short. Make them feel like adventuring is the best option and then continue your game as normal.

Just don’t forget about their past. Make sure that D&D prison breaks have some consequences and are never forgotten about.


D&D prison breaks can be extremely in-depth or a side adventure.

Planning and executing one can be a long and fun task. Make sure the players are always given new information and new hope so that they don’t get discouraged.

Keep the climax interesting, and make sure that the escape isn’t just the end. Survival and dealing with the consequences of breaking out of prison should be an omnipresent part of their lives.

I hope that I have given you some insight on how to run a prison break and how to make it impactful on your game.

Have you ever run a prison break? I would love to hear about it in the comments below.

Lastly, if you want to support the blog you can get stuff for it! If you want to have me as a professional GM/DM, then get more information on hiring me here at levelupgm. We offer The Cube as a custom add on to your game and our affiliates. At Dice Envy they offer well made and cool looking dice and Dungeon Vault helps to help give you extra tools to make your campaign even better! I prefer to use my dice from Dice Evy since they are actually balanced and love to use the tools from Dungeon Vault. We do have a Patreon if you want to support us more directly.

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1 Comment

  1. Excellent article! You totally saved my life with this
    I needed to plan a prison escape session in which my players need to free an ally and this came extra handy with all the examples and explanations

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