Advice for stealth missions in D&D

Stealth missions in D&D

Stealth missions in D&D are all about not making the mistake that everyone has made. That is, to spend 3/4 of the session on 1 character.

Stealth missions in D&D require you to be creative. You need to split the time evenly, go outside of the rules, and only give important information.

These are the major tips to learn about in this article, and that is why we will start with the most important tip: splitting the time evenly. There will be other tips that will help though, so be sure to read those as well.

Splitting the time

Little Timmy is playing a rogue. He as a rogue wants to go in and scout the entire base. You go through some rolls, describe the scenario, and look at that Timmy took 3/4 of the session time and everyone else was extremely bored.

If you focus too much on 1 person, everyone else will get bored. They are not on the edge of their seat trying to figure out what is happening with little Timmy. That would be metagaming and no one wants to actively metagame. Instead, they are waiting for their turn and no one is having fun except for little Timmy.

This is why stealth missions in D&D require you to split the time.

Splitting the time is making everyone get an equal portion of the playtime. So if you are playing for 1 hour and have 6 players, little Timmy will get only 10 minutes, if that. When in doubt, always give the group more time.

To some rogues out there this may seem unfair, but there are a few things to keep in mind. First, this is a group game. You are playing with others and for the sake of the group/table, everyone needs to be able to play the game. Letting 1 person have all the time makes a bad environment for others.

This is why I advise before someone does a solo mission that they understand this concept. They will be a little angry if they find out the group is doing things without them and they were not warned. So just give the player that information, or keep in mind the second option.

Second, there are ways to shorten the information and time spent on solo scenarios.

Give important information

“You go through the hallway and sneak past the guards, now what do you do?” “I check the storeroom.” Okay, you find 3 cheese wheels and that is all.” “That is all? What about a secret door. Is there a secret door?”

That is painful to watch.

This dungeon master decided to ask the rouge what they were doing every step of the way. This is a terrible idea and should only be done if the entire party is there. You will not have enough time to do this. There are much better ways of giving important information. Take a look at this example and compare it to the 1 above.

“You want to find out where the captain’s quarters are?” “Yes.” “Roll a stealth can investigate check.” “27 stealth and 69 investigate.” “You find a secret door that leads into the keep and were able to find a route the captain’s quarters without being detected.”

In the first example, we barely got through a part of the keep, and in almost as much time we gave the player thin information they wanted AND made them feel accomplished.

How to reduce the time spent on stealth missions in D&D is to:

  1. Clarify the player’s intentions before anything is done. Ask what they want to accomplish.
  2. Have them roll beforehand on whatever they need to roll. Try to avoid rolling twice unless your really need to, and only have them roll for skills that tie directly into what they want.
  3. Give a brief description of what happens and tell them what they find. Avoid too much detail. If you give too much detail, they will want to keep asking for more information. In fact, give them a map of the area if possible. Don’t make them explore it all if it is a big place.

With these 3 tips you will completely change how stealth missions are done and make them take a fraction of the time with the same result, or better.

If your players are in a group or want to try and stealthily slit a person’s throat while they are unaware, that is when you have to break the game rules or change them.

Instant kills

This is a contentious issue for most players and dungeon masters alike. The system of D&D does not allow for many instant kills. A dagger normally does not provide an instant kill, and therefore is a problem if players want to instantly kill someone.

The other side of this problem is that instant kills make sense. We know that if you slit someone’s throat in real life they are going to die. So why won’t it work in D&D?

Hitpoints. Hitpoints are what stop instant kills since the whole system is based around damage and HP. This is why many stealth missions in D&D work best if they are just for reconnaissance, but there are a few ways to deal with instant kills.

The first way to deal with instant kills is to use the system we talked about above. Have the roll a stealth check and tell them that they killed a few guards and hid their bodies. Pretty simple, but unsatisfying.

The second way is to lower the guards’ HP. Make their HP 11 or even lower, possibly 7 so that they can be killed. The player might have advantage if the guard is unaware, and will probably kill them that way. If you want to, you can even lower the guard’s AC since they are completely unsuspecting. If the guard survives he can call the real guards who have decent stats.

The second approach works well for when the whole group is active in a stealth mission, but the third option is the worst. The third option is what many novice DMs go for, and that is to allow players to instant kill with a successful attack/stealth roll.

The third option opens up a pandora’s box. Players now know a way to instantly kill people, and they will start arguing that sneak attacks are instant kills and so on. DO NOT GO WITH THE 3RD OPTION!!! This is what many novice DMs go with, and I hope that you will not have to deal with that headache that comes with this option.

There are other ways to do stealth missions that involve more detail, and it can be a full adventure!

Out of game information

For those DMs who love their game and are able to talk to a player outside of game, this might be an option for you. Have the player who is on a solo stealth mission text you or talk to you outside of game.

This is an option that will sound great for some, and terrible for others. You know who you are, but if you do this then you can give more detail to the solo stealth player.

I do not recommend in-between session stealth missions in D&D, but this is up to you. If you do so, just make sure that at the table if a stealth mission happens it will happen differently. Also, clarify that if you do not have time to do so in the future you retain the right to speed through any stealth missions.

Out of game information does not have to in-between sessions. Stealth missions in D&D happen at the table, and you might want to give the player secret knowledge. In this instance, pass notes or texts while the rest of the party is doing their thing.

This is an option for those of you who are able to handle multitasking that much. It is a tall task to handle, but if you are up for it this is another option for you. Just be confident in your multitasking before you attempt this.

Group checks and planning

If your players actually plan their stealth missions in D&D, they stand a higher chance of success. You should reward this by giving them an advantage or working something out.

This could be something as simple as having a person ready to help the rogue escape or having the entire group go with a map. Give some sort of advantage to your party if they plan.

This leads us to group stealth missions.

Most stealth missions are solo affairs. You have 1 stealthy person and the rest of the group can end up screwing things up with their bad rolls. A standard group check in D&D is after all having everyone roll and then seeing who failed and who passed. If half fails, you lose the check and the whole group fails.

This is why most solo players do stealth checks. To mitigate the risk of roll fails. There are some ways that you can have a group do a stealth mission though.

Make sure that they have access to pass without a trace. It is a great spell that makes everyone able to stealth and will make group stealth missions possible.

For other group stealth mission information, just look at the rest of the article. Split the time evenly, and use what we talked about for instant kills. You do not need to reduce the information since everyone is here and active.


Stealth missions in D&D can be a trap for DMs. If they decide to give a lot of time to 1 individual they are going to bore and possibly upset the rest of the party. That is why you need to split the time, and only give important information to those who are going on stealth missions.

For instant kills, it is a contentious topic. We have outlined 2 very good options to use and warned about another terrible option that some dungeon masters give.

Lastly, we talked about out of game options for you and how to deal with planning/group stealth missions.

I hope that these tips have saved you some time, and helped you deal with stealth missions in D&D more easily.

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