How do I allow the Rogue opportunities to be stealthy with a Druid in the party?

My party is currently level 6, and consists of a Halfling Rogue, Human Druid, Halfling Barbarian, and Half-Elf Monk. They're all excellent players who play tactically and know their class well. I'm currently running into a problem with the Rogue and the Druid.

My Rogue has Expertise in Stealth (+10 at this level) and a Cloak of Elvenkind. This means that her minimum roll (barring four 1s because they're a Halfling) on a Stealth check is a 12, and her average roll is around a 25. Even on a minimum roll, most NPCs will not be able to see her (and in a few levels that will extend to all NPCs).

However, the party's current methodology is to have the Druid do the sneaking instead of the Rogue. Their reasoning is that even though it's highly unlikely that the Rogue will get caught, if she does get caught then really bad things happen - the enemy will know they're being spied on, the Rogue gets captured, etc. However, the Druid is spying in the form of a rat, spider, owl, or other sneaky animal, so if a bandit spots a bat they probably won't think much of it. Additionally, the druid will have a much easier time escaping a secure location (say, by summoning 8 Giant Badgers and then Wild Shaping into a spider).

Here's my problem with this: I see "Being Sneaky" as a core part of a Rogue's class identity, and the player has invested a lot of resources (proficiency, expertise, and an attuned item) into being sneaky. I try to give all of my players a chance to live out their class identity: The Barbarian gets to hulk out and smash things, the Druid gets to save Dryads and heal cursed forests, the monk gets to take people down bare-handed, etc. I want to have at least some opportunities for the Rogue to get to experience this key feature of their class by sneaking into a secure location or scouting out an enemy party.

How can I design stealth-based encounters or challenges so that the Rogue will be a better choice than the Druid?

Encouraging them to have the rogue be sneaky doesn't necessarily require discouraging them from using the druid. Where possible, encourage them to work together. The druid can scout ahead to give the rogue information about the layout and the guards, create distractions, or keep watch while the rogue picks locks, dispatches guards, and the like. Each can handle the aspects of the challenge better suited to them, or give bonuses to their compatriot.

This has more players involved and opens up more interesting strategies.

The Vlad Taltos novels offer some good ideas. Vlad is an assassin (at least initially) but also a witch (Gender neutral term in the setting) with a familiar (Loiosh) who is essentially a tiny wyvern with an ecological niche very roughly in the vicinity of raven/raccoon/vulture/rat and they are telepathically linked. Loiosh is sometimes a distraction, often a scout, and always sarcastic.

Heist movies (Ocean's Eleven, etc) also give some good ideas for how to run co-op sneak this, as well as maybe some ways other part members could get in on it.

If you were running GURPS I would recommend making heavy use of Complementary Skills (Make a skill roll which then based on success gives a small modifier to another skill, possibly made by another player) For instance one player rolls Fast-Talk to distract a guard which gives a bonus (Or penalty on crit failure) to another player using Stealth. I'm not sure how adaptable this would be to D&D though.

• This actually might be the best answer for my particular group. My druid player would be very open to this, and a combination of their abilities would be far stronger than either one of them on their own. This lets them both have moments to shine. – Dacromir Apr 26 '18 at 22:22
• Considering that one of the reasons the players wanted the druid over the rogue was the fear of being caught, it's much better to have two characters caught who may be able to fight their way out together than a single character everyone else will have to rescue. – Captain Man Apr 27 '18 at 12:23
• the last example could be handled like this: Player A distracts Enemy X, so they give advantage to Player B (Same as 'Help' in combat). Or, use passive perception instead of a perception check. – C_Hawk Jan 24 at 1:36

You have a few options.

Don't change your stealth missions at all.

Instead provide a scenario in which the Druid is the only one that can do something with any reasonable chance of success, while at the same time the scouting has be done. In this case the Druid gets to shine and the Rogue does their sneaky bit, which can be resolved at the same time. This provides time as an enemy which is a great way to see how the players handle their resources.

Example: The party needs to scout the enemy camp before dawn but the locals have taken casualties... obviously in your party makeup the Druid is the primary healer and is the best choice to remain behind to take care of the wounded and the Rogue gets to do their thing at the same time. At the same time the Monk and Barbarian are aiding the fortification of the town to prevent skirmishers during the night.

Change the objective.

Secondly, if the objective is only to scout the Druid is arguably the better choice, but if infilitration into buildings is required or stealing a map or bypassing snares and traps are involved then the Rogue's involvement is much more attractive. The Druid will not have an easy time looking inside the Commander's locked desk to find out the troop movements as an example.

Behavior of the Enemy

Lastly, a hungry guard might actually take a shot at that curious squirrel to suppliment their low rationing. Or the guards could be warned against magical reconnaissance and to look for animals out of place. A Druid in Wild Shape trying to sneak around is noticable, most common folk in a setting like this are familiar with local flora and fauna so if an animal acts strangely it is something that could be noticed, if for nothing else to put the poor animal out of its misery because it is diseased (to say nothing of contamination of food and whatnot).

All this is contingent on who has the better Stealth check, it seems that the Rogue is far better and the likelihood of capture is low in most situations with good decisions.

• Giving the Rogue and Druid simultaneous tasks is a fantastic idea! However, changing the objective will be difficult as the Druid player is incredibly clever and has managed to bypass all of the obstacles you've provided. It's hard to make a trap designed to hit humanoids that also works on spiders, for example. Guards being more aggressive with animals acting strangely makes a lot of sense - in a world with magical familiars, this is something they'd watch out for. – Dacromir Apr 26 '18 at 22:17
• @Dacromir I personally use the optional Wild Shape rules from the UA with slightly extended times to learn them. It has worked well to quell the potency of such a versatile feature. – Slagmoth Apr 27 '18 at 0:41
• @Dacromir Nevermind magical familiars -- demons and monsters disguised as animals and possessed animals and the like are real things in this world. Superstitions about how to react to abnormal animal behavior can have huge survival advantages. Imagine how conservative most people are going to be when someone acting unusual of sorts means they might actually be controlled by a brain-sucking fiend. – Yakk Apr 27 '18 at 12:54
• This doesn't seem to completely address the question asker's desire to allow the rogue to feel like they play an important role as the stealthy, sneaky character. After all, your suggestion concedes that the rogue is a second fiddle sneak, only to be used when the druid is too busy to do the sneaking themself. The fact that the rogue can pick locks better than the druid is not a very good solution either, because slight of hand is an entirely different skill set; the rogue put points in stealth not lockpicking. – Pink Sweetener Aug 28 '18 at 12:50

Create scenarios that require resource management

Your players are right that a wild-shaped druid is a lot better at infiltration than a rogue. However, don't forget that a druid at your party's level only gets 2 wild shapes per long/short rest. A druid using a wild shape to do infiltration does not have that wild shape for any other future purpose, like combat. On the other hand, the rogue doesn't expend any resources to sneak--they can do it all the time, for free.

Therefore, you should create situations where the party has to consider whether the benefit of wild shape is worth the significant cost of using it for this particular infiltration. Will there be more combat in the future? Will there be other instances where being some kind of animal will be useful?

You don't even have to create such situations all the time. After you do it once or twice, your players will realize that they have to worry about resource management more generally, and might decide to send the rogue in instead of the druid.

Create scenarios that require hands

A wild shaped druid might be good at getting into places and looking at things, but a rogue has proficiency in thieves' tools and the ability to speak. If the infiltrator has to interact with other beings, or pick locks, or disarm traps, or steal something, or really anything other than observe things, the rogue is going to be the best choice. While the druid could plausibly return to humanoid form and wild shape again, they can only do that once, since they only have 2 wild shapes per rest.

Make the cost of detection very high

Right now, your players are deciding that the cost of the druid being detected is much less than that of the rogue being detected. However, if the cost of any detection is very high (the criminals will kill the hostage if there's anything suspicious, for example), then the calculation flips. The rogue then becomes the best option, because she has the lowest chance of being detected, period.

• The rogue then becomes the best option, because he has the lowest chance of being detected, period. The rogue also has the best options for eliminating guards before they set off the alarm. – LastStar007 Apr 27 '18 at 9:11
• Create scenarios that require hands - such as doors. Not even locked doors, just doors that you can't squeeze under. – Phil Apr 27 '18 at 11:26
• +1 for hands. The Druid may be better at infiltration, but the Rogue can open locked coffers/drawers to peek at documents, place/remove documents, etc... If the objective changes from infiltration to gathering information, collecting proofs, etc... then the Druid is just outclassed. – Matthieu M. Apr 28 '18 at 20:22
• If you are going to gender your answer, you should at least get the gender right. because he has the best chance vs. if she does get caught – Mark Booth May 1 '18 at 9:46
• Great answer. Non-arcane rogues I believe are the only class in 5e that outside of HP/HD and ammo have absolutely zero resources. Any scenario that is sufficiently drawn out and complex should favor the rogue's endless skill repertoire. – Duncan Aug 28 '18 at 18:07

There are several options...

Breaking into things a Wild Shape won't fit into

Chests, desks, and other secured containers are too tightly fitted for a wildshaped druid to get past. Gotta pick the lock to get into it.

Dealing with Guards

A wildshaped druid must Sneak. They only get 2 Wild Shapes per short/long rest and (until much higher level) cannot cast spells in beast form. If they chose a form that is particularly sneaky and innocuous, it won't be well suited for combat. A Rogue, on the other hand, hits like a truck without interfering with their ability to sneak. They can sneak up on and suckerpunch a guard to leave them unconscious (or dead), stuff em in a closet, and move on. A Druid has no choice but to try to sneak past them.

Additionally, just because a guard may not be suspicious of a wildshaped Druid doesn't mean they'll leave the animal form alone. A guard may try to stomp on a spider or rat, take a shot at a bird because 'rations suck, I want variety.' And if they hit you, it's going to break your Wild Shape...and a Druid's best options here are flashy, loud, and likely to draw more guards. The options you mentioned in the post are good for a "Screw the mission and save your skin" moment. A Rogue that gets spotted has a reasonable chance of laying out his opponent before an alarm is sounded, and doing so quietly. Or taking out that opponent before it even becomes an issue.

So, sure...a guard may not flip out if they see a rat. But if there's a guard directly guarding the only entrance into where you need to be, he's not just going to stand there absently while a rat tries to run past him under the door. He's at least going to kick at it and make a ruckus. A Rogue, on the other hand, could drop the guard, then go through the door.

Other Hazards

You turned into a rat to sneak into a castle. Better hope none of the cats that live in that castle notice you. You turn into a small bird to scout around a camp in the middle of the woods. You aren't sticking to cover like a smart, real bird would. A hawk sees you and decides he wants a snack. These aren't things that would happen to a Rogue.

Clearing the path

A Druid can probably slip past a lot of traps, locked doors, and snares along the way. This doesn't help anyone trying to come up behind them. If a rogue is acting as an advance scout for the party, they are likely leaving a clear, safe path for the rest of the party to follow.

A Sneaky Rogue isn't expending resources

A Druid that burns their uses of Wild Shape to scout is a Druid that has fewer uses of Wild Shape for other things....this is especially important for a Moon Druid, who is more reliant of their Wild Shape for combat.

Sniping/Assassination

Druids aren't generally going to kill someone quickly with a bow or a blade. Rogues are good at that, though. If the goal of the stealth mission is for someone to end up dead, the Rogue is a lot more likely to pull that off without bringing the entire guard force in the area down on their head.

Other Skills

Rogues have LOTS of skill proficiencies, and access to Expertise. Beyond just Stealth, a Rogue focused on Breaking and Entering may also be exceptionally skilled at Perception, Investigation, and/or Sleight of Hand. Scouting is only worth so much if you have a poor Perception check. A poor Investigation check leaves you more likely to trip over a trap. A Druid in an innocuous beast form would be hard-pressed to even attempt a Sleight of Hand check

Summary

If the goal is simply "Look at the enemy. See where they are. Come back and report." Then yes...a Druid is often the better choice.

But if something needs stealing, or there are guards to get past, or you need the rest of the party to be able to follow you in, or you need them to actually accomplish something once they get in there...a Rogue is by far the best at independent operation.

Theft

Thievery is a good start... Sure the Druid might be able to turn into a spider, and crawl through a keyhole, but if the needed item inside a locked box wildshape won't help much, especially if there's a need to retrieve the item "quietly". Reverse theft can also be interesting (planting incriminating documents or such). Additionally if theft of information is needed, a spider probably won't be that great at searching through documents, and de-wildshaping to read go snooping through the kings ledgers would probably require a stealth check without any circumstance bonus.

Traps

Another area that Rogues often will shine is spotting and disabling traps. While a bat or spider probably won't set off the trap, they also likely won't notice it, much to the party's woe if they do come through later.

Detect Magic

If the area that needs sneaking into has any kind of Anti-magic or Detect magic wards the wild shape druid will be affected/set it off. The Rogue might need to leave their Cloak of Elvenkind behind, but they'll still be more effective than the Druid.

• There is no circumstance bonus in 5e – David Coffron Apr 26 '18 at 21:23
• @DavidCoffron it's changed name. Advantage/Disadvantage replace all the many and various circumstantial boni from previous editions – Leliel Apr 26 '18 at 23:50
• @Leliel Advantage/disadvantage don't function the same as circumstance bonuses did and they don't replace all the bonuses that were incorporated in circumstance bonuses – David Coffron Apr 27 '18 at 1:19
• I'd argue that a spider not needing a stealth check at all was a circumstance bonus. – aslum Apr 27 '18 at 2:37

Let Players Help

I'm currently playing that druid. We have a rogue and a ranger, yet I'm the team's most efficient recon because MAGIC.

A town or two ago, we had just hit level 4, and our rogue had picked up the Disguise Self spell. We needed a count of the surviving orc force in the town we were trying to liberate.

I could have said, "Okay, same as the last three times we scoped out a town, I turn into a cat and look around." That seemed boring and not fun, so instead I suggested the rogue disguise himself as an orc, and I'd follow him as his faithful mastiff.

It was a good time. The rogue got to be put on the spot for some roleplay. He did stuff that seemed kind of dumb (it was late and we were all tired); I limited myself to Looking Toward [location] and saying "Woof!"; the other players said nothing (their characters weren't present). There were some laughs, and we advanced the story in a way that I think everyone enjoyed.

I realize this wasn't a "roll the stealth dice" mission, but it illustrates my point: Some players are fine with the idea of using sub-optimal strategies if it means increasing player involvement.

Use a roleplaying reason instead of a mechanical one

The way you've described it is as a purely mechanical issue. I'm hoping that your players actually give their characters more to them than just a bunch of numbers to be crunched against an opposing set of numbers.

Specifically: Play to the emotions of the characters (or maybe the players). Let's presume the druid is typical and loves animals and the forest. What if the enemy to be scouted was a group who was destroying wilderness, cutting down trees, etc. But the party had to quietly scout the area and not let the enemy find out they were being scouted. Will the druid idly sit by while scouting and let the destruction continue unchecked? I think not! So the rogue needs to go instead.

You could reverse it as well. Make it something that the rogue would need to be there "in person". Perhaps talk to someone that only knows the rogue and doesn't trust anyone else.

Those are just examples, of course.

Consequences and Realism

Sneaking around as a squirrel means you may occasionally get hunted by hawks or foxes. Even if you give the druid appropriate chances to notice and react, that's still a complication that the players may decide they don't want. They could go with a somewhat larger animal to avoid that issue, but that's more likely to draw attention from the intended targets.

The targets aren't necessarily dumb. Even if they don't know that a druid is after them, they will almost certainly know that druids exist, and that familiars exist, and that animal control spells exist, and that they could be targeted by adventurers. They're (probably) not going to freak out from seeing a squirrel, but they are likely to start getting seriously concerned if they see one acting oddly - and if they put the right preparations in place (heavy scent of wolf, for example), then even approaching the camp all that closely is going to be pretty odd behavior for a small animal.

...and then you can combine the two, for even more realism. Easiest way to get persistent scent of wolf is to keep a few semiferal wolves around the camp - and those things will happily go after any small furry animals that come too close to camp. Most targets, knowing about things like druids and familiars, will even approve of such behaviors. Even if the druid does act properly (like scampering up a tree outside the bandit camp) once they're treed, the bandit might pull out a bow to shoot them down, for the sport of it.

That's not to say that you have to pull this sort of thing every time, or that you should pull this every time, but if you start throwing in complications when the druid fails his stealth check you'll very quickly wind up with a druid who's a bit pickier about when he volunteers to be party scout.

Create encounters that Wild Shape will not solve

Guards will attack random creatures. Pests such as Rats, Spiders, Cats, etc need to shoo. The guard doesn't like cats, and this particular guard has a bad habit of kicking them.

I imagine a guard would stomp out a spider. Guards like to have fun too..."Hey Jimmy, I bet you 5 silver I can slice that rat in two with one swing." "Well maybe, but I bet you 7 silver I can shoot this rat with my bow on the first shot!" Guards attack, which would force the druid out of wild shape and then...oh no, he's just a regular druid in the middle of the enemy camp? That isn't going to end well, especially on his own with no way of contacting the party.

Make the mission more than just stealth

Druids can only stay in wild shape for so long. Put on the time pressure after a combat so the Druid, who is almost out of Wild Shapes, won't be able to sneak around for 3 hours.

Thievery is difficult for small things

Spiders aren't great at stealing things. Neither are cats or rats. Even if the cat or rat is able to pick something up, no guard in his right mind would let a cat run off with the parchment detailing the evil plan to dominate the world.

Assassinations are even more difficult

Druids are crappy at assassinations. Sure, they can sneak in and sneak out, but that requires them to use both uses of Wild Shape, and they still have to kill the guy. Can the druid get some good damage on the evil General sleeping in his room? Sure, but he can't get sneak attack plus guaranteed critical hit damage like the Rogue can. The rogue could one-shot the general, but the druid is just going to make him angry, and then the guards are going to be called and then it's just a mess for the Druid.

Make use of traps

The spider crawling through this door unfortunately didn't notice that the door is trapped with a Glyph of Fireball...ouch.

The cat going down the corridor failed to notice the pressure plate in the floor and the pitfall under the rug...the cat has now taken an axe to the torso and then has been dropped down a 30' pit. I hope he has another use of Wild Shape to get out of there...

Spiders can't pick locks

What's that? The window is locked, you say? Well, guess the spider/cat/rat can't get in there. Hmm, what about crawling under the door? No, you can't do that because it's a well-made door that goes very close to the ground. Unfortunately you can't fit underneath it.

Perfect, you got inside and you are in the room with the secret plans you need to scout. Only one issue remains: it's locked inside a safe that weighs over 100 pounds. I guess your options are to drop out of wild shape and try to carry the safe out sneakily, or to try to drop out, get the safe open by force (which will certainly alert the guards in the next room) and the re-shape and book it. None of those sound like great options.

Anti-Magic and Magic Detection

Wild Shape is a form of magic, being quiet is not. Any form of simple magic detection spell that will alert the guards when magic is detected will give the Druid away, forcing them to abandon the mission and leaving them unable to return.

Sure, you can get into the enemy camp, but the instant you set foot in the headquarters a magical alarm sounds and you know the jig is up.

I imagine enemy casters know Detect Magic. No reason why the Druid-spider wouldn't instantly be noticed as he crawls his way into the room, because the enemy mage gets a blip on his magical radar and casts Lightning Bolt, Hold Person, Dominate Person, etc on the Druid.

Turns out, the enemy mage in question knows Sleep. Uh oh, the spider with 1hp was put to sleep instantly with no save...and he wakes up in a room, with 4 walls, roof and ceiling with seemingly no way out. Or, perhaps there is a stone door that the Druid can't possibly fit underneath. He is now a prisoner with no way to escape and is out of action until the party rescues him.

The Rogue has more contingencies in case he gets caught

The Rogue has a very good stealth mod, you mention. Rogues are also able to Dash as their bonus action. The Rogue was caught? No problem, they can simply run 90' each round until they're away. Enemies shooting at them? They can still Dodge and run 60' per round. They'll outpace those bows quickly.

Alternatively, once the rogue rounds the corner, he can simply re-stealth and try to continue to hide from there.

Rogues also do ridiculous damage so if somebody is about to notice the rogue but hasn't yet, the rogue can simply knock them out with non-lethal damage in a massive alpha strike, or they can kill them and hide the corpse.

Conclusion

Yes, Druids are very good at sneaking, but that's about all a spider/cat/rat can do. Throw something else into the mix and the Druid will find themselves in an impossible situation because they aren't a Rogue. Anti-magic also plays havoc with Wild Shape.

Another thing to consider is multi-party member missions. Design a stealth mission that requires at minimum 2 people. That way, the Rogue and Druid are forced to both take part. Maybe they have to split up at some point, maybe the door only opens if both handles are pulled at exactly the same moment, and the handles are across the room from each other.

Think dangerous

Your Rogue has +10 with Expertise, that means her level is in the 13-16 range. At this level the party has few reasons to confront mere bandits — their enemies (as well as the environment) are usually more serious and difficult.

Give them new challenges, where Wild Shape wouldn't be so effective for sneaking:

• People know about magic in a magic world. A decent guard knows there are spells like polymorph or disguise self. An elite one has to have measures of seeing a suspect's true form.

• There are no animals here, so any conventional animal raises suspicion immediately. For instance, the party is questing in the City of Brass.

• Anti-magic measures are a necessary part of good defenses. You can't just teleport into the heavily defended Evil Lord's castle. Keep in mind you don't have to limit your world with the Player's Handbook — these defensive measures can be out of the players' spell list; for example, there could be permanent anti-magic field at the entry.

• The environment is dangerous for a sneaky animal like rat, spider or owl. These animals are not invincible. This is also true for low-level campaigns. Rats have bad sight, many animals prey upon them, other rats protect their territory. Spiders are squishy and have bad sight too, and owl is a desired trophy for any hunter; owls are territorial as well and have their natural enemies.

Predators

Next time the druid turns into a rat, have him get attacked by an eagle. It swoops down and stuns the druid, carrying him off into the air before he has time to react.

Does the druid shape shift in the air? This would certainly alert everyone to their presence, and potentially kill the druid when the eagle drops him.

Maybe he waits until he gets back to the eagle's nest, on the side of a cliff. When the eagle lands, he quickly shifts back into human form and desperately clings to the side of the cliff. The eagle, initially startled by the shapeshifter, perceives the druid as a threat to his chicks and starts attacking him.

The group, meanwhile, is searching for their druid, but how can you track an eagle without a druid?

Next time he turns into a cat, he has to make a roll, or he gets distracted by a female cat and runs off to have sex.

• Generally, smiting your players by DM fiat (Instant eagle! Carries you off before you can do anything!) is the sort of thing that generates player resentment. Doing it in a way that takes control from the character is even worse. Doing it with sexual overtones is worse still, and can feel like harassment. – Ben Barden Apr 27 '18 at 20:58
• If you wanted to implement this idea, a less forceful way of doing this would be to introduce the eagle's flying overhead well before talk of shapeshifting happens. This becomes a quiet deterrent rather than a loud punishment. – ale10ander Apr 27 '18 at 22:23