How do you prep/run stealth missions?

Come next weekend's game, my 10th level party* intends to assassinate the evil Lizard Emperor in his forward operating base within the jungle. They know it's full of lizardfolk warriors and dinosaurs, and that his mage advisor Nataxl is actually a night hag in disguise. The night hag is a secondary target, either for assassination or subduing and forcing to craft a particular magic item for the PCs.

During this week, they're devising their plan while I'm trying to prepare. Obviously, I want to include all the PCs without it being reduced to a bunch of Dexterity (Stealth) checks to see if they gain surprise or are noticed. I've attached the map I'm using for the Lizard Emperor's camp.

What are the best ways to prepare and run a sneaky assassination mission?

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The party includes:
  • Lizardfolk Rogue 6 (swashbuckler)/Warlock 4 (raven queen) who's stealthy as hell, has a special bird companion, and has magic items aiding in disguise
  • Grung Druid 10 (circle of the land) with the Hand of Vecna and making good use of pass without trace
  • Goblin Paladin 9 (oathbreaker)/Sorcerer 1 (wild magic) who is good with undead and has a small squad of goblin allies
  • Human Wizard 7 (divination)/Rogue 3 (mastermind) with an owl familiar, a crystal ball, and excellent at divination-based recon
  • NPC Artus Cimber, an archer wielding the powerful Ring of Winter
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Some notes I've made so far...
  • Players will want to recon the heck out of the forward base. I'll need a bunch of detail, but I'm concerned my players will go overboard here (I've seen them do it before) and then there's less time for executing the plan, and the rest of the session can feel rushed. So maybe I can come up with some kind of recon check which determines how much recon they can get through magic/familiars/scouting before realizing they're pushing too much and risk getting discovered if they try any more...
  • What if getting noticed is like the "click" of a trap, and then the player gets to react? For instance, the guard might only have noticed an unusual shadow or heard something or be about to turn their head. So the players get a reaction to save themselves, if they think fast.
  • Creating opportunities to hide should be important – extinguishing lights, distracting patrols, controlling weather, taking down and replacing a key sentry, etc. Successfully create the opportunity to hide? OK, you're hidden, no need to roll dice.
  • Stealth checks should be an option of last resort – if you need to make a Stealth check something has gone wrong and you're at immediate risk of discovery / the alarm being raised.
  • Though perhaps an initial group Stealth check (averaged) determine how close to the heart of the forward base the PCs get without being spotted. So perhaps I design 3 concentric rings of security – the outer camp (DC 10), the mid-camp (DC 20), and the inner camp (DC 30) – and their group Stealth check (averaged) determines how many they bypass. Though based on their Stealth scores and pass without trace it's pretty clear that an averaged result would be the mid-camp.
  • Because my party has scry + teleport tactics at their disposal, think of some advanced defenses vs. magical infiltration. Line of sight to the center of the base might be limited to prevent teleporting in. A lantern of revealing being used to scan for invisible creatures or scrying sensors (though its range sucks).
  • Make a random table with snippets of conversation – some humorous and some useful – for PCs to overhear. Stealth-based video games seem to do this well. And every time I've seen a player running a sneaking PC who comes across unaware enemies, they always want to eavesdrop.
  • Reinterpret Inspiration as a flashback mechanism to allow a player to say "Aha! But I remember when I…" and then describe some bit of planning their PC did that the players never actually planned for. This is borrowed from the Leverage RPG, but I really like it for D&D where plans rarely seem to survive actual play.
  • Think up several complications/twists, around one per PC, which I can spring to keep the players on their toes or use when something goes dramatically wrong.
 

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iserith

Magic Wordsmith
I would just do a set amount of specific challenges, perhaps 2 per PC (excluding NPC), that make sense for the adventure location and all point toward infiltration mechanically.

For any given challenge, at worst the PCs get progress combined with a setback on a failure until they've accrued a set number of failures (perhaps half the total number of challenges?) at which point the jig is up and they fail to achieve their ultimate goal, whatever that means in context.

The better able you're able to insert challenges in where they make sense (rather than follow a linear script), the better, so I recommend more abstracted ideas you can fit into the situation as it unfolds. To that end, just making a list of "infiltration complications" would be the way to go in my view.
 
I would just do a set amount of specific challenges, perhaps 2 per PC (excluding NPC), that make sense for the adventure location and all point toward infiltration mechanically.

For any given challenge, at worst the PCs get progress combined with a setback on a failure until they've accrued a set number of failures (perhaps half the total number of challenges?) at which point the jig is up and they fail to achieve their ultimate goal, whatever that means in context.

The better able you're able to insert challenges in where they make sense (rather than follow a linear script), the better, so I recommend more abstracted ideas you can fit into the situation as it unfolds. To that end, just making a list of "infiltration complications" would be the way to go in my view.
Thanks iserith. So sounds like you're alluding to a sort of skill challenge approach with "Schroedinger's complications"?

How were you imagining success/failure playing out at the individual challenge level vs. the overall mission?
 
Obviously, I want to include all the PCs without it being reduced to a bunch of Dexterity (Stealth) checks to see if they gain surprise or are noticed.
Minor thing you probably already know: if you do go with stealth checks at some point, do a group check. IIRC, they're still in 5e, and they provide a reasonable chance of a mixed group of highly/semi-/un- skilled characters actually succeeding at, well, something.
(ah, I see you're already planning on that)

also a good idea:
Reinterpret Inspiration as a flashback mechanism to allow a player to say "Aha! But I remember when I…" and then describe some bit of planning their PC did that the players never actually planned for. This is borrowed from the Leverage RPG, but I really like it for D&D where plans rarely seem to survive actual play.
Because my party has scry + teleport tactics at their disposal, think of some advanced defenses vs. magical infiltration. Line of sight to the center of the base might be limited to prevent teleporting in. A lantern of revealing being used to scan for invisible creatures or scrying sensors (though its range sucks).
I suppose you could assume that hag has set some stuff up, assuming non-combat magical abilities not in her stat block, perhaps. Maybe, if she has any reason to suspect the caliber of opposition coming for them, she could have a deal with a night hag to screw with scrying/divination, invade dreams of resting casters trying to recover spells, or other dirty hag tricks.
There's also all the classic ghetto tricks to foil invisibilty et al. The lizardfolk are likely comfortable on swampy ground, anyway, so choosing soft ground for their camp will also make it hard for anyone to approach without leaving very obvious footprints, they can incorporate bogs/quicksand and the like into their defenses, keep animals with keen hearing & smell and pay attention to them, etc...
 

iserith

Magic Wordsmith
Thanks iserith. So sounds like you're alluding to a sort of skill challenge approach with "Schroedinger's complications"?
I hesitate to call it a "skill challenge" because that comes with a lot of baggage. Here I propose just a series of obstacles to overcome which may or may not call for an ability check, depending on what the players decide to do about the obstacles. Adjudicate like any other action per the rules, but make the failure state always be progress combined with a setback instead of "you failed so now they're onto you."

How were you imagining success/failure playing out at the individual challenge level vs. the overall mission?
Without getting into specifics as to your scenario, basically any given obstacle cannot trigger a failure for the overall challenge. It's the accumulation of failure that snowballs into an undesirable result. A failed attempt to overcome an obstacle might instead be "success, but the next obstacle is harder" or "success, but it costs you some resources."
 

Bacon Bits

Explorer
In my experience, infiltration types of missions are not difficult to prep for as long as all you do is what the NPCs themselves actually have to do. That is to say, set up rough schedules of what the guards will be doing, what countermeasures the NPCs will have, and what the numbers of reserves look like and what happens when the alarm is sounded. Then you treat the entire mission as one block of XP.

Simply put, trying to force encounters to go a certain way with stealth and infiltration will just often not work because the my players almost never do things the way that you think they will. They will come up with multiple ideas that you never even considered so you won't have any plans to address. One of them will have disguise or illusion magic and walk right past your guards. Or they'll use charm magic to make friends out of enemies long enough to get what they want. Or they'll split up with one party causing a distraction while the others get what they're looking for. Or they'll have a timed distraction. Or they'll make a coordinated strike and hit fast and hard.

Don't think about what the party can do, per se. Think about what kinds of things the NPCs would be interested or could feasibly stop. Sure, the PCs can teleport and use scrying. Do the NPCs actually have secrets that could be scryed? Do they have other enemies that are known to teleport? How paranoid are the NPCs What kinds of threats do they already routinely face? What simple things can they do? Do they have perpetual light spells? Alarm spells? Arcane lock? Glyph of warding? Guards and wards? Symbol? Forbiddance? Note that many aburation spells are rituals. What kind of escape plan do the NPC leaders have? What do they care about the most? Who do the NPCs know that would sell or give them resources?

This kind of prep is when the DM gets to roleplay. You get to think like the NPCs and make plans and formulate them. Use your resources as best you can, and don't pull punches if the PCs walk into your preparations (but do have potential backups in mind if the PCs suddenly can't succeed). IMO, don't think so much about challenging the players as much as you are thinking about playing the NPCs correctly. You can always adjust the latter to fit what the former requires.
 
Minor thing you probably already know: if you do go with stealth checks at some point, do a group check. IIRC, they're still in 5e, and they provide a reasonable chance of a mixed group of highly/semi-/un- skilled characters actually succeeding at, well, something.
(ah, I see you're already planning on that)
Thanks Tony.

Yes, I know it seems like a deceptively simple question. Stealth mission? Make a group Stealth check! But I've seen stealth-based missions go wrong often enough to want to head off common errors at the pass, and instead make this something that engages all the players, builds tension, respects their planning but encourages them thinking on their feet, and with multiple possible outcomes for how the assassination goes down.

Also, at a certain point rolling a Stealth check, as a group check or otherwise, is not really satisfying. We know who the high Stealth characters are, we know that with pass without trace they can get numbers that will eclipse most opposition, so barring exceptionally bad rolls or ridiculously high monster's passive Perceptions they're going to succeed a group Stealth check.

So my idea to have them roll a group Stealth check up front to see how many "concentric rings of defense" they bypass is meant to do a couple things:
1. It scratches the player's itch/expectation to roll for Stealth. Psychologically, it sets the stage that you've already rolled Stealth...and now the adventure begins. Hopefully, this will be enough to counter my players' tendency to reach for dice when they say they want to sneak past a sentry.
2. It fast forwards past (some) defenses that my very detail-oriented players could easily get lost in countering, performing reconnaissance of, or otherwise mucking with.
3. It establishes that they're working together and this is not a scenario where the lone wolf – in our case, the lizardfolk rogue PC – is going off on his own.

I suppose you could assume that hag has set some stuff up, assuming non-combat magical abilities not in her stat block, perhaps. Maybe, if she has any reason to suspect the caliber of opposition coming for them, she could have a deal with a night hag to screw with scrying/divination, invade dreams of resting casters trying to recover spells, or other dirty hag tricks.
She is a night hag, currently disguised as a lizardfolk mage. She does know about the PCs and that they're dangerous, but she has other matters occupying her attention, like further insinuating her way into the Lizard Emperor's court & trying to find a magical shadow that she bound but has since escaped.

I've established that this night hag made pacts with goblins, turning them into redcaps. The theme I've got for her is "grotesque alchemist" who promises to make creatures better, stronger, more beautiful, or whatever with her brews, but her foul transformations only lead to tragedy.

There's also all the classic ghetto tricks to foil invisibilty et al. The lizardfolk are likely comfortable on swampy ground, anyway, so choosing soft ground for their camp will also make it hard for anyone to approach without leaving very obvious footprints, they can incorporate bogs/quicksand and the like into their defenses, keep animals with keen hearing & smell and pay attention to them, etc...
Yes, the camp is set up near water. The 10th level party does have magical flight capabilities, though at some point they will probably land (based on past stealthing) to approach on foot and avoid being spotted.

Footprints is an interesting point that usually doesn't come up when sneaking. Chances are the party will have pass without trace going, so it becomes a moot point.

The enemy lizardfolk have blood hawks (reskinned as archaeopteryx) which have Keen Sight.
 

Beleriphon

Totally Awesome Pirate Brain
I think what you want to do is look at the ultimate goal, and then place reasonable challenges in the way that make it seem stealthy, without having to use said mechanics.

For example, can the group draw a patrol off to create a hole in route long enough to do what they need? So if the patrol comes by a point every hour, then if they can get that patrol out of the picture then now they have a two hour window before anybody notices.

As a thought, getting to the Lizard Emperor probably shouldn't be hard, its the getting out alive that presents the problem. Lets pretend for a second they get into the camp, kill the Emperor, I'm assuming that isn't going to be quiet given the presence of a night hag. So, now we have a bunch of middling level PCs surrounded on all possible sides by enemies. How do they out is often more important than how to get in.
 
She is a night hag, currently disguised as a lizardfolk mage. She does know about the PCs and that they're dangerous, but she has other matters occupying her attention, like further insinuating her way into the Lizard Emperor's court & trying to find a magical shadow that she bound but has since escaped.

I've established that this night hag made pacts with goblins, turning them into redcaps. The theme I've got for her is "grotesque alchemist" who promises to make creatures better, stronger, more beautiful, or whatever with her brews, but her foul transformations only lead to tragedy.
That is just made of awesome.

She needs to find some way to get the PCs to find the shadow for her (like play out a scene when she notices they're scrying that makes them think it's in their best interest or something).

If the players /have/ figured out what she is, it'd be amusing for her to substitute a fake or actual lizardfolk mage for herself at an opportune moment. Challenge them to 'dispel her disguise!'
 

aco175

Explorer
I might make some skill challenged based on what the PCs would know when they reconed. Give they some choices on how to enter and proceed. Perhaps they notice a hole in the wall that they could sneak through, or a short distance covered with fine sand to detect invisible creatures. The owl may notice the first and the thief may notice the 2nd. Give them 4-6 options and let them choose the best path.
 
In my experience, infiltration types of missions are not difficult to prep for as long as all you do is what the NPCs themselves actually have to do. That is to say, set up rough schedules of what the guards will be doing, what countermeasures the NPCs will have, and what the numbers of reserves look like and what happens when the alarm is sounded. Then you treat the entire mission as one block of XP.
Thanks Bacon Bits.

Well, the hard part is prepping what the NPCs do in sufficient detail and verisimilitude! At least, that's my experience. I'm definitely planning to do a rough camp schedule, table of possible complications, table of overheard snippets of conversation, what happens when the alarm is triggered, total camp forces, and try to address some magical countermeasures to scry+teleport (these are the hardest for me).

Simply put, trying to force encounters to go a certain way with stealth and infiltration will just often not work because the my players almost never do things the way that you think they will. They will come up with multiple ideas that you never even considered so you won't have any plans to address. One of them will have disguise or illusion magic and walk right past your guards. Or they'll use charm magic to make friends out of enemies long enough to get what they want. Or they'll split up with one party causing a distraction while the others get what they're looking for. Or they'll have a timed distraction. Or they'll make a coordinated strike and hit fast and hard.
Oh! Maybe I wasn't clear? I certainly wasn't trying to force them to go a certain direction. The assassination plan was embraced by the players themselves. At the end of our last session they were presented with a couple options: (1) Assassinate the Lizard Emperor at his forwarding base camp where his defenses will be less extensive than in his capital city, (2) Stop a ritual by the Lizard Emperor's warlock emissary attempting to summon a demon lord, (3) Form an alliance with smaller lizardfolk tribes and wage war against the Lizard Emperor's Akabkan confederacy, and (4) Try to sow discord within the Akabkan confederacy to get the various evil lizardfolk power groups fighting amongst themselves. They discussed and choose #1.

Also, the sheer opposition of the camp is far in excess of what the party can handle – I telegraphed this through allied NPCs sharing some info to the players, and because I have a pretty good handle on their upper limits based on past encounters. This seems to have dissuaded them from a head-on assault. For your reference, once the PCs bypass the three concentric rings of defense, the camp (if encountered all at once) probably amounts to 120,000 adjusted XP. For reference, my party with their NPC allies have an adventuring day XP budget of around 50,000.

Don't think about what the party can do, per se. Think about what kinds of things the NPCs would be interested or could feasibly stop. Sure, the PCs can teleport and use scrying. Do the NPCs actually have secrets that could be scryed? Do they have other enemies that are known to teleport? How paranoid are the NPCs What kinds of threats do they already routinely face? What simple things can they do? Do they have perpetual light spells? Alarm spells? Arcane lock? Glyph of warding? Guards and wards? Symbol? Forbiddance? Note that many aburation spells are rituals. What kind of escape plan do the NPC leaders have? What do they care about the most? Who do the NPCs know that would sell or give them resources?
Do the NPCs actually have secrets that could be scryed? Yes, absolutely.
Do they have other enemies that are known to teleport? No.
How paranoid are the NPCs? Very. The Lizard Emperor has schemes within schemes, and his forward camp is at the fringes of his territory, a few miles from a sacred site revered by multiple lizardfolk tribes.
What kinds of threats do they already routinely face? The general territory – the Valley of Dread – has numerous threats like goblins, pterafolk, spirit nagas, undead, dinosaurs, etc.
Do they have perpetual light spells? Alarm spells? Arcane lock? Glyph of warding? Guards and wards? Symbol? Forbiddance? Potentially alarm, but none of the others. The warlock emissary is not present (he's back in the city). The night hag disguised as a lizardfolk mage "Nataxl" is an innate caster with at-will detect magic & magic missile, and 2/day each: plane shift (self only), ray of enfeeblement, & sleep. Being a hag, I can give her "weird magic" that suits her theme. Also, the Lizard Emperor can innately cast 1/day each: darkness, pass without trace, & silence. And his two sub-chiefs – who I'm still writing up stats for – might have 8th level ranger spellcasting, meaning up to 2nd level ranger spells, of which alarm would qualify.

What kind of escape plan do the NPC leaders have? The Lizard Emperor can become invisible in dim light and darkness, so he would use that to escape until he could reach one of the few quetzalcoatlus mounts/out-fliers. The night hag simply will cast planeshift or use Etherealness to escape...though is a way for the PCs to convince her not to flee (if they're not trying to kill her).

What do they care about the most? The Lizard Emperor wishes to unify/conquer all lizardfolk tribes, destroy any rival lizard kings, and then conquer the land to take it away from humans/goblins/undead and establish lizardfolk on top. The night hag is trying to recover a magical shadow of the god Semuanya that escaped her magical binding; she is concerned this failure will inspire derision from her coven sisters, or possibly punishment by her master Acererak. They are camped by the sacred site – Semuanya's Birthing Stones – to make sure the fractured god Semuanya is not restored, and also hoping to incite local tribes to being first aggressors in order to justify seizing the sacred site.

Who do the NPCs know that would sell or give them resources? The Lizard Emperor and his forces are already well-supplied by the Akabkan lizardfolk confederacy & their capital city. The night hag may have traded with her coven sisters for weird magics.

This kind of prep is when the DM gets to roleplay. You get to think like the NPCs and make plans and formulate them. Use your resources as best you can, and don't pull punches if the PCs walk into your preparations (but do have potential backups in mind if the PCs suddenly can't succeed). IMO, don't think so much about challenging the players as much as you are thinking about playing the NPCs correctly. You can always adjust the latter to fit what the former requires.
As you can see, there's a lot of moving parts. One of my challenges is distilling all this into actionable usable things at the table that support the player's desire for a stealth-focused assassination mission.
 
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I think what you want to do is look at the ultimate goal, and then place reasonable challenges in the way that make it seem stealthy, without having to use said mechanics.

For example, can the group draw a patrol off to create a hole in route long enough to do what they need? So if the patrol comes by a point every hour, then if they can get that patrol out of the picture then now they have a two hour window before anybody notices.

As a thought, getting to the Lizard Emperor probably shouldn't be hard, its the getting out alive that presents the problem. Lets pretend for a second they get into the camp, kill the Emperor, I'm assuming that isn't going to be quiet given the presence of a night hag. So, now we have a bunch of middling level PCs surrounded on all possible sides by enemies. How do they out is often more important than how to get in.
Thanks Beleriphon. Yes, I'm thinking along those lines of establishing challenges (complications as @iserith recommends) that feel "stealth-themed" but don't involve Stealth checks. My hunch is that each challenge/complication might cover one "zone" of an abstracted map, at least until the group gets to the heart of the camp.

Yes, absolutely, part of the challenge is getting out alive and also making sure none of the enemies tie the assassination to the friendly lizardfolk tribe (the tribe of the lizardfolk PC which did the initial recon and has sent two lizardfolk warriors along with the PCs at their request).
 
I might make some skill challenged based on what the PCs would know when they reconed. Give they some choices on how to enter and proceed. Perhaps they notice a hole in the wall that they could sneak through, or a short distance covered with fine sand to detect invisible creatures. The owl may notice the first and the thief may notice the 2nd. Give them 4-6 options and let them choose the best path.
Thanks aco. By choices of entry, do you mean things like (1) Fly over, (2) Aquatic ambush, (3) Disguised as captives of lizardfolk, (4) Stampede distraction, and so forth?

See, I was thinking that any and all of those tactics might be used over the course of gaining entry. So they might fly past the outermost defenses, but then land to avoid being spotted, some might hide in the water to approach from one direction, while the others sneak in to some dinosaurs and try to upset them as a distraction, and then if the lizardfolk PC and the human PC get spotted together, the lizardfolk PC might think fast and pretend to have caught the human. Separating everything out as a distinct skill challenge of its own seems like it might artificially discourage this kind of organic integrated approach, doesn't it?
 

Spohedus

Explorer
Regarding your concern about them going overboard with recon, I would start the session with "You have successfully spied out the base over X hours or days and determined the following weaknesses to exploit.....". Gap in the guards, environmental weakness (river, etc), daily delivery, whatever. Give them 3 or 4 choices of things to exploit and let them roleplay which way to play it.

I like the idea of making it easier to get in, but much harder to get out. That's better story telling since the initial invasion will be filled with player-induced tension ("how do we avoid bringing the place down on our heads!"), while the latter half will have them puckered up good to get out alive.
 
Regarding your concern about them going overboard with recon, I would start the session with "You have successfully spied out the base over X hours or days and determined the following weaknesses to exploit.....". Gap in the guards, environmental weakness (river, etc), daily delivery, whatever. Give them 3 or 4 choices of things to exploit and let them roleplay which way to play it.

I like the idea of making it easier to get in, but much harder to get out. That's better story telling since the initial invasion will be filled with player-induced tension ("how do we avoid bringing the place down on our heads!"), while the latter half will have them puckered up good to get out alive.
Thanks Sphoedus. Oh man, I am so tempted to do that "after spying for X hours/days you learn..." There's a couple reasons I'm on the fence...

First, the night hag may use Nightmare Haunting on a caster PC, preventing that PC from getting a long rest. I'm on the fence whether or not to do this. The night hag would know that the PCs were in the general area (the Valley of Dread), but she would not yet know their current location in a cave of friendly lizardfolk (one of her sisters knows, but hasn't yet communicated that), and she certainly doesn't know the PCs are planning a bold assassination on the Lizard Emperor's forwarding base camp. It's a risky move and until now the party has been fairly cautious. For instance, they faced one of the hag's sisters many sessions ago, attempting to ambush her, and nearly the whole party was put to sleep (thanks to dust mephits cooperatively upcasting sleep & that hag using enhanced component to upcast sleep), leaving it up to the druid PC to soothe that hag's ruffled feathers and convince her to spare the party in exchange for tribute.

Second, my players are very detail oriented. In other words, I can rarely describe a scene without being bombarded by questions. It's not a bad thing – what else am I doing as DM if not answering the player's questions? But it can get excessive. For example, even with your approach, I could say something like "ok, there's a slow-moving swamp river running through the camp" and then I'd be getting hit by: (1) Ok, I'll send my arcane eye underwater. What do I see? (2) I want to scout ahead of the party before we decide to go this way, popping up intermittently like a crocodile. (3) How deep is the river? How wide? Are there any reeds? (4) If I have a light on the bottom, will we be able to see, and will a creature on the surface see the light? ...and so on, you catch my drift. It's very hard for me to present options without my players turning over each option with a barrage of questions asking for clarification and detail.

Third, one of my players wants to plant a friendship tree between his race (grung) and the friendly lizardfolks they're staying with. This is a side thing to wrap up some story threads, explain a plant growth spell cast in exchange for an elixir of regeneration, and provide one last "gathering of the fellowship" before this very dangerous mission. Rather than interrupting the flow of the assassination with dramatic role-play (not my players' forte), I told the player we could open the session with that scene he proposed.

Ideally, I'd love for the players to tell me their recon strategy in advance, but the realities of work, school, and family life mean that I rarely get much information from them in advance beyond the bare minimum. For example, even after I posted my question here, my players questioned their original plan to go forward with the assassination and had a whole vote off thing where they ultimately confirmed that, yes, they were sticking with the assassination plan. If past is anything to go by, I'm doubtful if I'll get much more than that from them. That's OK. It just means I need to get creative with how I fairly but expeditiously handle recon.
 
I hesitate to call it a "skill challenge" because that comes with a lot of baggage. Here I propose just a series of obstacles to overcome which may or may not call for an ability check, depending on what the players decide to do about the obstacles. Adjudicate like any other action per the rules, but make the failure state always be progress combined with a setback instead of "you failed so now they're onto you."

Without getting into specifics as to your scenario, basically any given obstacle cannot trigger a failure for the overall challenge. It's the accumulation of failure that snowballs into an undesirable result. A failed attempt to overcome an obstacle might instead be "success, but the next obstacle is harder" or "success, but it costs you some resources."
I see! You're supporting a fail forward approach to stealth missions?

Let's see if I can correctly offer a specific example incorporating that general principle... A PC attempts to use animal friendship on a lumbering dinosaur (to get it to move, thus providing cover for the party to hide behind), but the dinosaur succeeds on its Wisdom save. The spell doesn't work and the dinosaur begins baying in agitation. Several lizardfolk guards come over to investigate.

At this point, the party retreats back into the jungle... which makes the approach of the lizardfolk guards seem like a non-complication. Now the PCs just circle around to another positions – like the one the guards just abandoned – and try to slip in there.

Or is that a bad example?
 

aco175

Explorer
My group tends to be action oriented in that I can give them a few things they see and they ask a few questions and may do some scouting to gain a few options not already discovered, but they will act after only a few minutes of discussion. Your group appears to be a bit different than mine.

I guess I would prepare a few ideas that I think they may pursue and ad-lib the rest. I try to keep the group together, but if they wish to try to infiltrate in several directions I think that that just means greater chances of being found out.

You always have great ideas here so it should be fine.
 

iserith

Magic Wordsmith
I see! You're supporting a fail forward approach to stealth missions?
Perhaps not for all, but in this case it seems like a reasonable choice for what you are trying to accomplish as what you seem to want to present is a more dynamic scene. (I also use "progress combined with a setback" since that is laid out in the D&D 5e rules. "Fail forward" is a term that can be confusing as many people will define it differently.)

Let's see if I can correctly offer a specific example incorporating that general principle... A PC attempts to use animal friendship on a lumbering dinosaur (to get it to move, thus providing cover for the party to hide behind), but the dinosaur succeeds on its Wisdom save. The spell doesn't work and the dinosaur begins baying in agitation. Several lizardfolk guards come over to investigate.

At this point, the party retreats back into the jungle... which makes the approach of the lizardfolk guards seem like a non-complication. Now the PCs just circle around to another positions – like the one the guards just abandoned – and try to slip in there.

Or is that a bad example?
Typically, "progress combined with a setback" is used for a failed ability check, but there's really nothing stopping you from using it when narrating the result of the adventurers' actions in other situations. Presumably, the lizardfolk in your example represent a new complication for which the PCs must declare some new actions in order to overcome it. That might just be retreating back into the jungle, but can they do so unseen and unheard as suspicious lizardfolk search the area?

In truth, I do not in any way concern myself with actions the players might take. I just focus on presenting interesting complications that follow in the situation. I highly recommend it.
 
Typically, "progress combined with a setback" is used for a failed ability check, but there's really nothing stopping you from using it when narrating the result of the adventurers' actions in other situations. Presumably, the lizardfolk in your example represent a new complication for which the PCs must declare some new actions in order to overcome it. That might just be retreating back into the jungle, but can they do so unseen and unheard as suspicious lizardfolk search the area?

In truth, I do not in any way concern myself with actions the players might take. I just focus on presenting interesting complications that follow in the situation. I highly recommend it.
Yep, definitely trying to prepare interesting complications that are suited to a stealth-based mission.

But there's also a point where those two things meet – actions the players might take, and presenting interesting complications. In order to be interesting, the complications I present need to be meaningful challenges based on the PCs' capabilities and strategies/actions the players lean towards. A DM needs to think of both, right?

For example, my players have taken to using pass without trace frequently while their PCs are sneaking about the jungle. This gives +10 to their Dexterity (Stealth) checks. The PCs have Stealth scores of lizardfolk rogue +13, human wizard/rogue +7, grung druid +1 (uses enhance ability for advantage on Dex checks when sneaking, so actually more like +6), and goblin paladin +1 (usually Helped by the wizard/rogue who's a mastermind, so that's advantage, so actually more like +6). And that's not counting a few other spells. That means that the lowest Stealth checks the PCs can roll are 24, 18, 17, and 17, which beats passive Perception scores of the lizardfolk (13). And if treated as a group check, they always succeed against a Perception check or 17 or less.

Another example is that my party has a crystal ball which allows them to cast the scrying spell at will (given 10 minutes). One of them can also cast teleport using the Hand of Vecna. This means they can scry the Lizard Emperor's routine and try to teleport in while he's at his weakest. And so as part of my prep I need to include a schedule which accounts for what the Lizard Emperor is doing, say, hourly throughout the day. This sort of defined schedule isn't something I'd normally include in my prep – the PCs' capabilities and possible actions necessitate that I adjust my prep to account for that.
 

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