Escaping prison: system analysis and strategic planning

As I discussed in my articles Bael the Thief – part 2: prisoner practice, and Heroic Thief: the process of making a villain a hero, part of taking my thief character build and story, and ascending them past being a petty criminal is the process of allowing him to fall and then redeem himself.

As such, and important component of the thief experience in that regard was failing as a thief.  Not only did it allow me to understand the consequence of being immoral through the game’s systems such as losing inventory items and skill progression, but it also taught me about the challenges the thief faces.

For example, the jail represents a harsh punishment, but it also stands as a challenge to the player’s  commitment to living outside the law.  When the player gets sent to jail they face 3 unique obstacles when attempting a successful escape from prison:

  1. Escaping the cell: the player is given a single lockpick and must break out of their jail cell using it.  If the player loses their cool and breaks their lockpick they will be forced to spend the duration of their sentence in jail and lose the progress they’ve made towards the next level of all of their skills.
  2. Sneaking past the guards: once the player has gotten out of their jail cell they must now sneak past the guards patrolling the area in order to get to the exit, this requires an understanding of their patrol patterns.
  3. Retrieving possessions from evidence: after sneaking past the guards the player must still break into the evidence chests to retrieve their possessions.  This can be accomplished with the one lockpick they had from their jail cell which is risky; an alternative that I have found to be useful is to pickpocket one of the patrolling guards for the dungeon key and use that on the chests.

Leaving a key for next time

To really cut my teeth on the prisoner life, I went on a brazen crime spree around Whiterun and allowed myself to be taken to jail whenever I got caught, knowing full well that this was all part of my practice with being a thief.  Each time I broke out of the jail I felt like Houdini,  mystifying guards with my sneaky abilities.

Bael escaping Whiterun’s dungeon through the sewer systems

Whiterun’s dungeon is deceptively easy to escape since there is a novice level lock on a sewer grate within the cell that allows the player to escape by bypassing the need to sneak past the guards within the dungeon.  The sewer tunnel ended up in the guards’ barracks meaning that I would have to walk back to the dungeon and pick guard’s pocket within it to get the key I needed to open the chests, around the fourth or fifth time of breaking out of Whiterun dungeon, I noticed that the only real challenge I faced was getting caught pickpocketing the key from the guards.  It was at this point that I realized I could just plant the dungeon key I would need later within a barrel along the path that way I could just grab the key, walk into the dungeon, grab my things, and off I’d go for another lap of stealing, getting caught, and escaping.

A video of my escape from Riften jail:

System analysis and planning

While a prison break is a funny system to analyze due to its moral implications, it did get me thinking about how at its most base level I was looking at a system and problem solving for a more efficient solution, based on the challenges I had learned and faced on my previous attempts. Thinking of things as their own components and composing a plan to address each element of the system is no minor feat, yet we do it almost without thinking in games.  By recognizing that this is a matter of problem solving and strategic planning we can begin to understand the power of games to help us grow in our capacity to think through things and plan for the future.

Have you ever found yourself approaching a problem differently after playing a challenging game? Do you believe that practicing problem solving in games can translate to the growth of our ability to understand and plan for problems that we face in the real world? I welcome discussion on this topic and if you have experiences of your own you wish to share please do so in the comments below, or write in to

Play Professor is the blog of ludologist and video game journalist Andrew Mantilla. You can check out more of his content on FacebookTwitterInstagramand Youtube.

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