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I think I've gotten the wrong end of the stick when it comes to what and when the DM should be calling for rolls when the party is exploring a dungeon.

Picture your typical D&D dungeon crawl. There's winding passageways, a handful of monsters on the prowl, one or two traps and a couple of secrets. My party, understandably, wants to move stealthily, keep an eye out for traps, and watch for secrets. We're playing in roll20 with dynamic lighting on, so they can only see a few squares in all directions, making travel treacherous.

As it stands I end up having them advance a few squares at a time, calling for a new perception check every time they find a new passageway, asking for stealth checks every now and again and having the rogue roll to look for traps each time they wander down a new hall.

This feels clunky, repetitive, and subject to goblin dice. The more they roll, the more likely it is someone will fail badly enough to be spotted by a monster or fall prey to a trap. However, running the entire dungeon on a single set of rolls seems to be against the whole spirit of dungeon crawling; why bother to explore a dungeon at all when a single roll has determined your fate?

I'm aware of the rationale behind long empty hallways in premade maps. In an ideal world you'd design a dungeon crawl that was only rooms, and parcel out your checks per room. But what about a cave system? There's no "rooms", per se... the whole map IS long, possibly empty "hallways". Sometimes you really are trying to navigate a large area with no obvious beginning or end.

I'm sure I'm missing something here... when, and how often, should players be rolling when dungeon crawling?

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Passive checks are your friend

First, you can probably replace nearly all of your checks with passive perception (PHB 175):

A passive check is a special kind of ability check that doesn’t involve any die rolls. Such a check can represent the average result for a task done repeatedly, such as searching for secret doors over and over again, or can be used when the DM wants to secretly determine whether the characters succeed at something without rolling dice, such as noticing a hidden monster.

This is usually done for perception, but you can also employ these for things like stealth as well. Passive checks let you automatically deal with all of those... passive rolls.

Only call for rolls when they matter

DMG 237 sums this up nicely:

Remember that dice don't run your game- you do. Dice are like rules. They're tools to help keep the action moving. At any time, you can decide that a player's action is automatically successful. You can also grant the player advantage on any ability check, reducing the chance of a bad die roll foiling the character's plans.

Parse your dungeon crawl into specific scenes

You can avoid repetitiveness by clearly delineating the dungeon crawl into individual scenes. You allude to this issue when you talk about a dungeon that's only rooms. Basically, instead of thinking of the dungeon in physical terms, you should think of it in game scenes, and gloss over the unimportant parts.

For example, in a dungeon crawl I've run in roll20, sometimes I will just reveal a hallway or an empty room and say "there's nothing in here". Likewise, I don't move avatars or reveal areas on the map until it's actually relevant--I only use the map when the map is necessary. Doing so saves a lot of time that would otherwise be wasted rolling dice for no good reason. You can still create a sense of tension by throwing in a handful of red herrings, too.

Once your dungeon is set into scenes, you can make scenarios that matter. Instead of having your players stumble through a dark cave, rolling along the way, you can say "You grope through the darkness for a time, making good progress. In the distance, you notice the glow of a campfire...". You might notice that movies do this a lot: a character might be navigating a cave or dungeon, but viewers don't see all of it--only the parts that are somehow significant.

By viewing your dungeon as a series of important scenes, you can make every die roll somehow significant, and therefore streamline your dungeon crawl.

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  • \$\begingroup\$ All good points! However, given your last section, how do you handle it from a physical perspective? As in, if your players would need to move their tokens around the map, do you just not reveal the map until there's combat that would require it, or do you move them in a large jump to the next relevant area, or...? \$\endgroup\$ – Alex Apr 1 '18 at 0:44
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    \$\begingroup\$ @Alex That seems like a separate question involving tokens and maps; these are not the default for 5th edition, but instead an optional rule. I would recommend asking how to handle tokens when long halls or tunnels are on the map as another question. \$\endgroup\$ – David Coffron Apr 1 '18 at 0:55
  • \$\begingroup\$ @Alex I've edited my answer to address that, but basically yes. I don't think it's necessary to keep the map constantly updated. \$\endgroup\$ – Icyfire Apr 1 '18 at 2:37
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One thing you can do to reduce the amount of back and forth turn-based advancement is to make a Party Token that everyone has control of and for which they share sight. Have the party elect a mover for the token. PCs can still do any rolls they need to, but you have eliminated "Bobby Moves and Acts, Sheila Moves and Acts, Diane Moves and Acts, Eric Moves and Acts, Hank Moves and Acts" from the equation.

As the party token advances, at any point a character can call out that they are looking for secret doors or ask about some feature they see. Keep all of their tokens handy for quick placement in case of an encounter, preferably tucked away behind a dynamic Lighting curtain.

It's a lot more abstract, but if you feel the need to role-play long hallways and intersections, it can really cut down the interplay.

Two more things: First, avoid the pressure to keep everyone in initiative-based movement. Describe the party as a whole and let players ask for an action as they need it. Second, remember passive checks, this is the sort of thing they are made for.

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    \$\begingroup\$ While I've never used roll20 I have always effectively worked with this sort of system. The party indicates how they are arranged, everyone retains their position relative to the leader unless they say they are doing something else. \$\endgroup\$ – Loren Pechtel Apr 1 '18 at 21:27
  • \$\begingroup\$ As soon as minis are on the table, virtual or no, the great temptation is to go with turn-by-turn action. \$\endgroup\$ – keithcurtis Apr 1 '18 at 21:38
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Design your dungeons to invite action

Rather than having meaningless long corridors, make the corridors meaningful.

I accomplish this by having regular patrols in dungeons where it makes sense or giving some surprise encounters in caves that I can spring on the party when they take too much time in an area. After a bit of these (when the party struggles to stay alive with the limited resources they end up with after all the extra encounters), they realize that moving quickly can also have advantages.

Also, consider a time incentive

This question has many good answers about a related issue involving the drawl of certain playstyles. If your party spends 30 minutes moving to the next hall, maybe the ritual they were trying to stop has already finished and they have to flee from the demon prince that was resurrected, and later be chastised by the king who sent them on the quest. Perhaps the king's diviner was scrying on the party and informed the king that they were too careful in the dungeon, prizing their own well-being over the well-being of the kingdom.

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    \$\begingroup\$ as a player I have come to expect that NPC actions always progress at the speed of plot and neither haste nor tardiness effect the eventual timing. Although some combats are easier if entered rapidly, denying the opponent a chance to fully buff. The choice between a head-long charge at the archmage and a painstaking gradual advance could prove critical. \$\endgroup\$ – Jasen Apr 1 '18 at 2:38
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    \$\begingroup\$ That's a playstyle choice for the DM. In my world, that would absolutely not be a valid assumption. My NPC actions proceed at the speed of what the NPC can do, by the rules of the game, and characters can absolutely make their jobs harder by giving the NPCs plenty of time to prepare, or easier by proceeding with all due haste. \$\endgroup\$ – Phil Boncer Apr 1 '18 at 16:06
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How I handle situations like this:

When you enter terrain like this you make one check. I save that check for the next situation where it's needed. At that point I have them make new checks unless they failed the check and the consequences aren't immediately known. (Thus not revealing that there was some hidden consequence.) I also have new checks after things like fights or breaks at the table.

Combine this with treating the party as a single unit in non-combat situations and such exploration goes quickly unless they hit terrain where they can't make up their mind.

I've also had the party respond to a maze with "we're following the right wall". Extra walking but it played faster. Since they were actively trying to clean out the dungeon wandering encounters weren't a downside. In the end I didn't even try to map the maze for them. (And never threw a maze at that group of players again.)

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