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My party currently is actively hiding from the law. To put it into context, they've murdered 4 civilians and about two dozen guards in their recent exploits. Reasonably, the various villages, towns and other population centers are aware of them and have posted they are "wanted" throughout these areas. The party was given a task to interrupt a festival that will be taking place in one of the towns. They can disguise themselves, but I guess I'm wondering, will they have to make saving throws throughout their time in the town? assuming they don't want to be noticed. If they decide they want to be more secretive, but they are well known and actively wanted in the area, how would I work that in to this session mechanically? This is my first time DMing, and so any insight you could provide would be endlessly appreciated.

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2 Answers 2

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This is a case for (contested) ability checks

Saving throws are not the appropriate mechanic for this. From the Player's Handbook (PHB) p. 178,

A saving throw - also called a save - represents an attempt to resist a spell, a trap, a poison, a disease, or a similar threat.

Saves are for when something happens to a character that they must resist. This does not match the task you have described.

The mechanic you are looking for is an ability check, possibly a contest. The situation you describe has characters using their abilities (using proficiencies in Disguise Kit, Deception, Stealth, Performance, or any other plausible idea they come up with) to try and thwart the abilities of someone else (the Wisdom (Perception) or Wisdom (Insight) of the townsfolk).

Ability checks are described in PHB p. 174. I encourage you to read that whole section.

An ability check tests a character's or monster's innate talent or training in an effort to overcome a challenge.

You may decide on an arbitrary fixed difficulty class (DC) for the check, based on how hard you want the task to be. You may set the DC from the passive score of the townsfolk's Wisdom (Perception) or Wisdom (Insight) (i.e. 10 + all the modifiers that normally apply to the check). These fixed DCs would be suitable for when the party are not facing direct scrutiny; they have walked into town with their disguises, pretending to be nonchalant, and you want to determine if they raise any suspicions, so you call for the party to make an ability check.

If, however, the party does something to draw unwanted attention then a different kind of ability check may be appropriate: a Contest. Maybe they're trying to sweet-talk their way past a guard, or they did something flashy and now have drawn everyone's attention. In a contest, the player rolls their check normally, but rather than rolling against a fixed DC, the opponent also makes an ability check, and whoever gets the highest succeeds.

My suggestion in this scenario would be to call for an ability check when they enter the area, whenever they do something which draws unwanted attention to themselves, and possibly whenever they transition to a different area. Allow the players to describe how they approach this task, then you as a DM decide what skill and ability are appropriate. (Avoid having players simply call "I roll Deception" or similar. Instead, they should say "I lie about my identity", then you say "Roll Charisma (Deception)".)

Use multiple fail states

Beware that each ability check is a possibility for failure, and each player rolling is a point of failure. It would be unbalanced for the entire session's plans to hinge on a single bad roll. A way you can have multiple rolls while still maintaining some dramatic tension is to use multiple failure states.

The bad scenario would be, on the first failed roll, the entire town immediately sees through all the disguises and the guards swarm the party. The session then instantly switches from a game of sneaking and intrigue to a big combat. Not ideal.

The good scenario would be, on the first failed roll, one person gets suspicious of the party. "Hey, why do you look familiar?" The party is still in stealth mode, but things have gotten slightly trickier because now someone is probing their disguises. The party will need to dissuade them somehow. Maybe, on the second failed roll, the guards start noticing the party acting strangely and send a couple of their number to shadow the party. The party will want to shake them off their tail. And so on. Each failed roll does not instantly cause a failed mission, but it incrementally ratchets up the tension and the town's alertness.

You can hear more about using many fail states in this running the game video by Matt Colville.

In short, this is an excellent time to use ability checks. Call for ability checks when the party attempts to use their skills to overcome some challenge. A success lets them achieve their goals. A failure means they face some opposition (although, ideally, just enough opposition to make things interesting but not so much opposition that it shuts down the adventure).

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    \$\begingroup\$ I love the progression from being hidden, to being seen, to be suspected, to being recognised, to being confronted/reported/chased. Gives so many opportunities for player choices, feels fair, but also empowering and that golden feeling that you're finding/building the story together. \$\endgroup\$
    – StuperUser
    Apr 25, 2023 at 10:58
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@BBeast's answer provides an excellent overview of how to handle this mechanically, so I wanted to provide some additional thoughts on how to approach the overall situation from a DM perspective.

What kind of adventure is this?

When the players get to the town, it's up to you as the DM to decide how involved the process of being and staying disguised is going to be.

The main point to consider here is the importance you want to place on the disguise/stealth aspect of this. Is this an Assassin's Creed-style infiltration where the focus is on moving through the town, avoiding detection, and completing their objective unnoticed? Or are you really just wanting them to get to a more interesting encounter/fight that you've set up for once they get to the centre of town during the festival?

Knowing that in advance will help guide what situations you put in front of the players as they go about their task, and how something like different fail states might play out.

What checks should they be making, and how often?

When considering what kind of skill checks or other challenges the players might face as they go through the town, you should consider the town itself. You can ask yourself some questions like:

  • Is the town on high alert for criminals, or are the player's crimes just general outlaw behaviour that people are mostly ignorant to?
  • Is the town expecting someone to disrupt the festival?
  • Are the town guards specifically alert for disguised criminals?
  • Are there any bounty hunters/stronger law enforcement hunting the players?
  • Are common people aware of the player's appearance, enough to pick them out of a crowd? Are certain people (like bartenders) more aware of the wanted posters?

A town on high alert, checking all visitors closely, provides a far different challenge to one where everyone is just going about their daily business.

Allow player creativity, and be ready to adapt

The situation as described provides a lot of options for the players, and they might come at it from angles you didn't predict. You might prepare an encounter at the main gate where the guards inspect the players as they arrive - but the players opt to swim into town via the river, or climb an outer wall, or tunnel under the wall, or fly over the wall.

When given a goal like this, players will have a lot of fun with heist-style planning and hijinks, and you should allow that as best you can. Telling them they have to go through the main gate because that's what you've prepped is going to leave a sour taste in everyone's mouth.

When planning specific encounters, try to design them more generically to allow them to work wherever needed in the town. Maybe the conversation you'd planned for the guards at the front gate could instead be with a random patrol, or with some off-duty guards your players ran into at the inn? Don't tie events to specific people or places if you can avoid it - or at least plan for generic settings like 'a shop' or 'an alley' instead of 'this exact shop' or 'this exact alley'.

If the players come up with a creative plan that they're invested in and you think is cool, consider whether you're willing to adjust some of what you've prepared (including changing DCs) to help their plan to succeed. Some DMs won't do that, and at some tables 'fudging' like that is just not done (and that's perfectly fine) - but if you think that, say, skipping a guard patrol encounter will make the infiltration feel more cinematic and fun, it might be worth it.

Have some contingencies

If everything goes wrong, what's going to happen? There are many ways the player's plans can fail, some are more impactful than others - but if it all goes wrong, they're discovered and all hell breaks loose, what's next?

It sounds like your players have no qualms about killing guards when push comes to shove - so is there going to be a big fight? It's probably a good idea to have a large town square style fight prepared with a number of guards, and ideally some opportunities for the players to disengage and try to escape.

Is that fight going to disrupt the festival enough to complete the player's goal anyway?

Is it likely they'll be captured without fighting to the death? That might be the end of the session as you prepare a prison escape sequence for next time, but maybe there's an opportunity to turn the capture into a part of their disruption of the festival as well?

Have fun with it

You're all playing a game after all. It's your first time DMing, and I would hope your friends are understanding of that, so don't expect it to go perfectly - things will happen that you didn't plan for, and you might need a minute to think about what should happen next. That's okay. As long as everyone is enjoying the story, you're doing your job just fine.

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