[RPG] How to make sure the players escape but feel like it was because of their wit

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Setting

I'm preparing for my first time as a DM in D&D 5e (as a player I have gotten to level 4 in 3 campaigns so I have a good grasp of the game, in my group everyone wants to have a go as DM and as players so we switch campaigns a lot).

My plan is to have a gladiator style story in a Roman-empire–type world. For the first session I was planning to have the players be captured1 and forced to fight in an arena from which they should escape2. From there they will have to flee to another empire. (Which empire they flee to and which route they take should give me enough to build a real story on and give them some influence over the story.)

1 How do I go about capturing the players?

Do I tell them before they make their background? It might make certain things easier example:

It would make sense for "the Romans" to confiscate some equipment which they haven't even used, that would be quite annoying. Should I just tell them to not prepare equipment, because it was confiscated?

On the other hand it could be quite fun as well to at the start of the session begin with a short story about how each player was captured and how they will have to fight against other prisoners.

Or should I maybe make it a real combat encounter? But for this I would have to make sure it is an unfair fight which sounds like a bad idea.

2 Main question: How do I make sure they escape?

My story relies on them escaping otherwise they would just be stuck in an arena for the entire campaign. I don't want to make this trivially easy but I still need to make sure it happens. The only thing I can think of is to provide many many was for them to escape:

  1. They could kill a guard guarding the gate while fighting in the arena, this would be a very public way to escape which could have some side-effects, like civilians helping or attacking them.
  2. They could steal the keys from a guard while he sleeps (maybe with the help of something like mage hand).
  3. And as a final backup: they could win their freedom as prize for winning if they just can't figure out they're supposed to escape.

Is there a better way to do this? Do I have enough opportunities to escape? Both real options seem quite miss-able. (Do you have any other ideas? Just letting the jailer forget to lock their cell seems kinda lame.)

Best Answer

The first rule of RPG plots is that no plot survives contact with player characters. You cannot rely on players to do what you expect. If a puzzle has two solutions, the players will invent a third, and you will need to be responsive to that if you want to avoid the feeling of railroading.

Your main risks are as follows:

  1. The plot requires the PCs to be captured, but given the chance, they may evade capture
  2. The plot requires the captured PCs to attempt escape, but they might not even try
  3. The plot requires the PCs to succeed in their escape attempt, but they may fail
  4. You need the PCs to feel responsible for their own successful escape, but they not come up with a plan that justifies the success mandated by the plot

Have the campaign begin with the players already captured. Tell the players in advance that this is the starting premise of your game. It conveniently allows the PCs to keep their starting weapons and equipment (they're gladiators, so those are the tools of their job). This also explains how they know each other and prevents the very real danger that the PCs will win or escape from a fight they're supposed to lose.

Next, the PCs must be motivated to try to escape. If the players do not decide upon this spontaneously, you must create that motivation. Have an NPC gladiator give them a warning that the arena is planning to set the PCs in an unwinnable fight where they'll be slaughtered (against a golem, manticore or the like, as a grand spectacle), and must make a run to escape.

Let the PCs come up with their own escape plan, but if they're entirely clueless, have the NPC help (he knows how to escape, but needs the PCs because they're going to have to fight their way out). Be responsive to player ideas, even if you had something else planned.

If the players escape based on their own plan, they will certainly feel that they did it by their own wit. However, the next best solution is if they fight their way out, so that they feel responsible the success of their own escape.

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