Running a D&D Prison Rescue

Picture this: one of the characters punched a town guard in the face and is now being held in prison. Instead of having them lawfully serve their time, the party has decided that the obvious solution is to break them out of prison. They might choose to just charge in, but many players may opt for a stealthier approach. The question then becomes how you’re going to run this as a Dungeon Master. I’ve put together a few things that I’ll be using to help keep things fast paced, exciting, and challenging.

In today’s article I’ll cover:

• Using Flashbacks for Prison Rescues
• Designing the Prison
• Understanding the Prison’s Security

Using Flashbacks for Prison Rescues

I discovered using the Flashback mechanic through a podcast and thought it seemed like a lot of fun. Originally these are rules meant to be used for running heist jobs, think Ocean’s Eleven planning room, but I think the mechanic should apply to prison rescues nicely. After all, rescuing somebody from prison is essentially a heist. There is something valuable (in this case a person) guarded by various security measures (prison and whatnot) and the party must ‘break-in’ in order to obtain (rescue) that valuable. Flashbacks do not need to be entire 20 minute scenes, but rather just a brief description of what’s happening and a couple of ability checks or social interactions.

Full Disclaimer: I haven’t actually put these into place (yet), but I think the party is close so I want to be prepared. If I think of any tweaks after actually using it I’ll come back and update the article. For more information check out the actual rules from Blades in the Dark and u/HauntedFrog’s take on it.

The basic idea is that the party is able to spend time planning, in character, so that the players don’t have to at the table. Instead of planning every single detail and possibility, the players can come up with creative solutions as they are required. Whenever the characters come across challenging obstacles, they are able to state how their characters would have retroactively ‘prepared’ for this situation during the planning phase. The players state the end result of a flashback, and you as the DM must decide whether it is reasonable or not. This could include having specialty items prepared (explosives, spell components, forgeries, etc), or gathering intel that might be useful (location of doors, windows, guard patrols). There are a few limitations and rules I’ll be putting in place to hopefully keep things from getting too hectic.

Rules for Flashbacks

1. Players have a limited number of flashbacks they are able to use equal to their Intelligence Modifier (minimum of one).
   • For example, a Wizard with an Intelligence of 18 would get 4 flashbacks, while a Barbarian with an Intelligence of 8 would get 1 flashback.
   • My campaign uses an alternate system for inspiration (check it out here!), and the Blue Powerbands can be optionally used for a flashback instead of inspiration. 
2. Players may call for a flashback at anytime they wish. However flashbacks cannot change or modify anything that has already been established.
3. To initiate a flashback, players ask “Could I have…” followed by what they are trying to accomplish. 
   • If the request is basic and can’t be fucked up – such as asking ‘Could I have brought 300 ft of rope with me?‘ – I would grant it to the players without costing a flashback, only the cost of the item.
   • If the request is a bit more complicated than simply running to the store – such as asking ‘Could I have followed that guard home yesterday and found personal information to blackmail him with?’ – then the player can expend a flashback and you guys run the scenario to see what happened.
4. Flashbacks are not guaranteed to be 100% successful.
   • Flashbacks may end up being partially successful or have unintended consequences depending on how the scenario ended.
   • However, if something extreme happens that would drastically alter present reality – if the players get killed or captured for example – then the flashback fails and the party immediately returns to the present.

Designing the Prison

Normally I’m all about making things up on the spot and preparing as little as possible, but I think for this scenario it’s best to actually have concrete things prepared. The more details you have “ready to go”, the easier it will be for you to convey the world to the players and respond appropriately to their choices. In order to understand how the prison is secured, you should first think about the prison’s layout and design.

The easiest way to do this is by creating a map or a blueprint! If the prison already exists in the campaign’s world, be sure to keep any existing details in mind as you plan. Additionally, if you have a map handy it opens up the possibility of the party acquiring a blueprint. In my campaign, for example, the party has a blueprint for the Western Wing of the prison and will (probably) be using it to plan a bit of their strategy. This way I can just either reveal part of the map before the rescue begins, or create a separate blue version of the map in a handout. 

You have a couple different options when it comes to map making. I’ll be using DungeonDraft, which is absolutely awesome and you should definitely check it out. It’s a simple and intuitive way to make high quality maps for only $20. I’m not getting paid, I just really like it. There are plenty of other programs available or you can always just use regular pen and paper. Regardless of what you use, you’ll want to keep a few things in mind during the design phase.

• How large is the prison, and how many prisoners can it accommodate?
• Are guards permanently stationed here or do they leave every day?
• How many wards or wings are there?

It might take a while to design the prison, but be sure to do some research (ie Google “prison floor plans”) and base it off of actual prison designs. There are, apparently as I’m just learning, four common prison designs used in the US: Radial, Telephone-Pole, Courtyard, and Campus. You certainly don’t have to stick to any of these, but use them for inspiration when creating your own. Remember it doesn’t have to be – and probably won’t be – perfect. 

Here’s a list of things a common prison may include:

• Prisoner Cells
• Recreation Area
• Guard Quarters
• Inmate Possession Locker
• Kitchen
• Warden’s Office
• Visitation Area
• Secured Prisoner Entrance/Exit

Understanding the Prison’s Security

Now that you’ve got the layout of the prison figured out, it’s time to figure out how each area is kept secure. I can’t really plan this part for you, since the specifics all depend on your campaign and the prison itself, but I can prompt you with some questions to get the ideas moving along.

• How intense is the security? 
  • This is related to the type of prisoners that are being held here. Dangerous prisoners require greater security.
• How many guards would be required to reasonably watch over the prisoners?
  • What sort of patrol or schedule do the guards have?
• Are there any locked-off or highly secured areas?
  • If so, how can these areas be bypassed or unlocked?
• Where are the entrances and exits to the prison?
  • Most prisons will have very few entrances or exits, and may likely only have one. You should also think about whether or not there are windows, and how many. 
• What is the protocol if and when shit hits the fan?
  • In the event that the party is discovered, how will guards react? Is there an alarm system in place?
• What magical systems are in place?
  • If the prison is high security, there will probably be various glyphs, magical traps, barriers, and alarms in place to ensure that no shenanigans are taking place. 

Hopefully these questions help you understand how the security works at your prison so the players can successfully (maybe) rescue their comrade! If you have any questions or comments, please send them to aaron@thealpinedm.com. Thanks!