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Wisdom from the Master: Actual Stealth Missions

This article was first broadcast in Episode Sixty-Nine on 17th April 2019.


Lennon: This doesn’t bode well for my idea of having my players run a stealth mission.
Ryu: What does that have to do with anything?
Lennon: Well the whole party isn’t made up of Rangers, Rogues, and people who can cast “Invisibility” so they’re going to make it what? One, maybe two rounds before the guardhouses are alerted and we’re on the express train to murdertown.
Ostron: Well, that depends on how you set up the encounter.



If the hype and excitement around the release of Waterdeep: Dragon Heist showed us anything, it’s that a lot of players and DMs are excited about the idea of doing a heist or stealth infiltration encounter in their games. There are probably visions of the characters being a coordinated team of misfits like in Oceans’ 11 or the Italian Job, or they’re a skilled group of operators sent on a quest reminiscent of a Mission Impossible scenario.

However, what most players and DMs actually experience is the characters finding a guarded location that can be snuck into, but they barely make it in before half the group fails a stealth roll and all the guards come charging. Seasoned groups usually have a different approach; they compare everyone’s stealth scores and, unless they *are* all rangers and rogues, they decide they may as well just ring the alarm bell themselves and get all the guards in the main foyer; at least there’s room to move and maybe cast a fireball during the unavoidable fight.

In fairness to those groups, D&D is not set up to allow a stealthy approach most of the time, and the main reason for that is guards. In almost every movie or video game where an individual or team are sneaking around, they are able to recover from mistakes, divert the guards away from their posts, or subdue them quietly and immediately. D&D’s rules as written are fairly limiting in that respect, and a lot of the convention with dungeon design doesn’t support a stealthy approach either. However, there are ways to get around or overcome the issues, and we’re going to cover some of them here.

We’ll start with the biggest thing that trips up most groups; Stealth checks. There are usually two challenges here: who is making the stealth checks, and what happens when they fail.

First up, the instinct of most groups is to try to bring everyone along. As we said, for most people they’re thinking a fight is inevitable and they’d rather have all hands on deck for that. To deal with this problem, we look to the movies that are doing stealth or heists. In most cases, only half or a smaller portion of their whole group is involved in the actual infiltration of a site, because only those people are good at it. Everyone else is doing something else that relates to their strengths.

Most D&D settings are not going to have security cameras someone will need to hack into, but if you’ve got a spellcaster with arcane eye, they can serve much the same function. Heck they can literally do the same job because there’s no range limit on the eye, so they never have to leave wherever base camp is.

If you’ve got a bard or any character with a lot of pluses in Performance, they can cause a distraction that might draw some guards away from key watch posts and cause enough of a disturbance to attract the attention of other posted sentries. Or if someone has a lot of proficiency with Persuasion or Deception, they might be able to draw off some of the guards before the heist even starts and convince them of some sort of enticing activity or distraction that will keep them from work.

Now, if your players don’t seem to be aware of alternative options for infiltration, you can helpfully nudge them along. If they have some sort of NPC leader figure working with them, their boss can make suggestions for how the party might approach the job. Or if they’re just working on their own initiative, an old bar regular or retired thief could be overheard telling a story about how their crew used one of the tactics on a different heist.

Of course, there are going to be guards that will stay at their posts regardless. Maybe they’re new, and they haven’t allowed the crushing drudgery of their repetitive existence to lull them into the kind of complacency that leads to depression and binge drinking and disregard for responsibilities. Or maybe they’re magical constructs. Anyway, eventually the characters are probably going to have to sneak past someone, and here it comes! The inevitable single digit die roll that causes the guard to pounce on the careless intruder and summon twenty of their comrades!

But that’s not the way it has to go. See, unfortunately the way D&D sets up skill challenges there is often a sense of black and white to them; there’s a check DC, and rolling below it means failure. However, there can be granularity to failure if you allow it.

First of all, Stealth checks are usually opposed by passive or active perception checks. If the guard’s passive perception is 10 and the stealth roll was an 8, it would make sense that the guard noticed *something* odd, but why would they immediately jump to the conclusion that it was a ranger sneaking along the stairwell and make a beeline to them? I mean, this is a pseudo-medieval setting; you know how many rats were around? They might instead start making active perception checks, giving the character the choice of backing off or not moving to improve their chances of stealthing successfully until they *can* sneak by.

Another common trope in stealth and heists is the immediate distraction. Throwing a rock, impersonating a colleague, sending a false message, basically anything that gets a guard or guards to move somewhere else long enough to sneak by. This can involve deception, persuasion, or performance checks depending on what the characters are trying to achieve and what the situation is. It’s also a scenario where non-combat spells like Prestidigitation, Minor Illusion, and Disguise Self can shine.

But, again, eventually you’re going to find the guard that knows all the tower rats by name and what they sound like, they’ve memorized their duty roster, and the only one they’ll obey new orders from is the reigning monarch. You’ve got to take them out. Here again is another issue where the rules can get in the way. As written, the D&D rules stipulate that knocking someone unconscious requires you to reduce them to 0 hit points with a melee attack. Now, there are a few poisons that can render someone unconscious, but again you have to hit with an attack, and there’s usually a save they can make to avoid that. There are also spells that can do enough damage to kill someone in one hit, but do you really want to waste Disintegrate on a random guard when you’re 80% sure his boss is going to be violently angry at you in the very near future?

One option is to try to homebrew a solution, like going back to the 3.5 rules and looking up how coup de gras attacks worked, but we think there’s a better solution; rethink how the dungeon’s put together.

Most D&D dungeons are designed with combat in mind, so all of the creatures present are designed to provide a challenge to the characters in combat, in that it will take more than one round to eliminate them. But it’s worth stepping back and considering the place the characters have in the world. Characters in D&D are supposed to be extraordinary, particularly as they climb beyond levels 1 and 2. Compare that to the average CR of “Common” NPCs, which is 0.

The point is that if this isn’t a lair explicitly full of monsters that are universally hard to eliminate, like gnolls or giants, it wouldn’t make sense that all of the people there are able to stand toe to toe with the characters. That would be like the Royal Welsh using the SAS for guard duty. Or for our American listeners, that would be like a Marine base using Special Forces to guard the doors.

So the point is, if this is a location the characters are supposed to sneak into and there should be a chance they’ll succeed, don’t put elite guards on patrol. The NPC Knight creature would be a good challenge for level 3-5 characters; it has 52 HP, it can probably hold its own for a bit, and it certainly can’t be taken down in one shot by characters at that level. But what self-respecting knight is going to patrol hallways?  Your average Guard NPC from the Monster Manual, on the other hand, has 11 HP — even a level one character has a decent shot at knocking them out if caught by surprise, and it’s almost guaranteed with two. The best part is, that’s following rules as written, so you don’t have to worry about trying to make up mechanics on the fly or borrow rules from older or other systems.

Now the above solutions assume that failing stealth checks completely is going to be a relatively rare occurrence where one or two die rolls went horribly wrong, but what if the party insists that every member has to be part of the infiltration team? Obviously the half-orc in full plate with a -1 Dexterity is not likely to ever make an impressive Stealth roll, so the whole endeavor isn’t going to be stealthy beyond a few feet, is it?

Fortunately there’s still a way to save the players from themselves by the use of group skill checks. With group skill checks the rest of the party can cover for members that are bringing up the rear in terms of skill rolls. You as the DM determine the DC  as usual and then if half or more of the party makes it, it’s considered a success. How many party members need to succeed and what the DC of the check is can be adjusted as necessary, but it allows for the possibility of the whole party coming along even with the Bard carrying the one man band that is his preferred instrument. It also allows for a lot of roleplaying options as the characters can think up story rules for how the rogue might be helping muffle the paladin’s armor or the wizard is using his magic to clean up the dirt the barbarian is leaving where he walks.

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