Skill Challenge: Prison Break

by Ameron (Derek Myers) on June 18, 2009

From time to time the PCs may find themselves incarcerated. There are plenty of reason why this might be the case, but I think it’s fair to say most PCs will try to escape if the alternative is life imprisonment or execution. How the PCs ended up in prison and what happens to them when they get out is entirely up to the DM. This skill challenge just focuses on scenarios the PCs may find themselves in while incarcerated. This can be run as one large skill challenge or a series of smaller ones.


The PCs are thrown in prison. They may be looking at hard labour, a life sentence or even execution. Unless they are content to die behind bars, escape is the only option. While imprisoned the PCs are given sub-standard rations and begin suffering form malnourishment and fatigue. If an escape plan is in the works, it should be attempted soon.

Why are the PCs in prison?

  • The PCs need information from a prisoner. The only way to meet with him face-to-face is to get thrown in prison along side of him. The PCs may pretend to be known criminals or may deliberately commit a crime in order to be thrown in prison.
  • The PCs have been framed for a crime they did not commit. The accusations are false, the evidence planted and the magistrate bribed. They have no chance of beating the rap honestly.
  • The PCs are guilty. Whether they knowing committed a criminal offensive (with good reason of course) or whether they unknowingly broke a law they were not aware of, they have ended up in prison.


If this is run as one large skill challenge it should be a complexity 4 or 5. However, this might work better as a series of smaller complexity 1 skill challenges.

Primary Skills

Athletics, Acrobatics, Bluff, Endurance, Heal, History, Stealth, Streetwise, Thievery

  • Each skill can only be used to accomplish 1 success towards the overall skill challenge unless noted otherwise.
  • Skill checks denoted as assist do not count as a success or failure towards the overall skill challenge.

Other skills

Diplomacy, Insight, Perception

Inside the Prison

Acrobatics (hard DC)

Tumble gracefully from a balcony to gain access to a restricted area.

Athletics (moderate DC)

Climb over a wall to gain access to a restricted area.

Diplomacy (moderate DC, assist)

Earn favour with guards or other prisoners to gain information about the prison or guards.

Success: +2 to Streetwise or History.

Insight (moderate DC, assist)

Ferret out sympathetic guards and prisoners.

Success: +2 to Bluff check.

Intimidate (moderate DC)

Show strength in the face of a challenge to earn respect of fellow inmates.

Streetwise (easy DC)

Learn who the power players are in the prison – inmates and hacks.

Streetwise (medium DC)

Learn about the prison layout.

Streetwise (hard DC)

Learn the most likely location of weapons and equipment.

Thievery (hard DC)

Create improvised thieves tools from common items found in the prison.

Escaping Your Cell

Bluff (hard DC)

Fake illness convincing the guards to come into your cell.

Endurance (hard DC)

Keep up your strength despite harsh conditions and poor food.

Heal (moderate DC)

Fight off infection or disease due to poor conditions and rotten food.

Insight (moderate DC, assist)

Ferret out sympathetic guards.

Success: +2 to Bluff check.

Perception (moderate DC, assist)

You act as the look out while attempting to escape from your cell.

Success: +2 to ally’s Stealth check.

Thievery (hard DC)

Pick the lock of the cell. The PC must have some kind of tools, even if improvised.

Escaping the Prison

Acrobatics (hard DC)

Tumble gracefully from a balcony to gain access to a restricted area.

Athletics (moderate DC)

Climb over a wall to gain access to a restricted area.

Athletics (hard DC)

Climb over the wall to escape the prison grounds.

History (moderate DC, maximum 2 successes)

Recall or learn something useful about the layout of the prison.

Perception (moderate DC, assist)

You act as the look out for anyone sneaking around the prison or climbing the wall.

Success: +2 to ally’s Stealth check.

Stealth (moderate DC)

Move about the prison without detection.

Stealth (hard DC)

Avoid detection in the yard.


The PCs manage to break out of prison undetected. Which is not to say that they won’t be missed. They have a limited amount of time to put distance between themselves and the prison, but for now no one is looking for them.


The PCs are either caught before they escape the prison or manage to just make it out when they are detected. If they are caught before they escape then they will face severe punishment and most likely be moved to a more secure area (making future escape attempts more difficult). If they do manage to make it over the wall, they are spotted during the escape. Guards will be after them immediately. The chase is on.

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