D&D 5E Rolling Without a Chance of Failure (I love it)

Often I see the following DM advice:

"Don't ask for a roll if failure isn't interesting."

I totally understand this advice.

As a player, though, I disagree. I love to roll. In most situations, I'd choose to roll a check than not roll and automatically succeed. Even when failure isn't interesting.

In my experience, this guideline often leads to my DM saying, "Oh, your character has a high History bonus, so I won't make you roll for it."

Though that makes sense narratively... I've invested in History! I want to roll!

However, I understand that a failed History check really isn't fun. Just saying, "You don't know anything about that" doesn't really lead to interesting narrative outcomes.

In the game I run, I almost always ask players to roll. I've tried to find ways to always make failure a little interesting, even when success is guaranteed.

Here are some examples:

A rogue is trying to pick a lock. It's not a difficult lock, and they have time, so I'll tell them "you are going to succeed, but roll to see how effortless it looks." On a low roll there's a lot of sweat and broken lockpicks. On a high roll they pick the lock with a bent paperclip and a wad of chewing gum.

A barbarian is trying to cut a chain in two. They're a barbarian, they'll get through it in time. I'll have them roll an attack roll to see if it makes a loud noise or not, alerting creatures in the dungeon.

A character with the Soldier background is commanding a lower-ranking guard to move aside. Because of their background feature, they will succeed. But I'll have them roll a Persuasion or Intimidation check to see what the guards think of them after - are they in awe, or suspicious, or annoyed?

Do you ever do this? Rolling even without a chance of failure?
My main problem with this is (a) it's not always easy to come up with "flair" or a "stylish" way of doing things (I would know, I've been working on that very thing for my DW game, more below), and (b) several of these sound like special punishments that only come up because the character has relevant talent/expertise. Now instead of having the reward of success for investing heavily in something...they get new forms of failure? That doesn't sound right at all to me. E.g. the guard being "suspicious" of the order sounds like a much worse problem than simply refusing to obey, or similarly breaking the chain with a loud noise sounds like a punishment for rolling badly at something one is good at--if the weenie wizard tried, they'd either get simple success or simple failure, not "and now you alert the whole place to your presence!!"

Now, it's possible it's just these specific off-the-cuff examples, that is, these weren't given the kind of thought that you would give in the moment. But I find that it's a big risk with this sort of thing, where a high degree of skill or ability with something no longer translates to being "good" at it, but rather to being even more swingy at it, which is...not to my taste. Out of curiosity, do you also enjoy things like the Wild Magic table for chaos sorcerers?

So, I have created house rules for playing "Legendary" characters, cribbed from a friend's game who did the same thing, but expanded. Basically, DW normally caps out at level 10. After level 10, you're supposed to either retire the character or swap to a new playbook and start again. That's...not interesting to me. So I reused and expanded these rules for playing high-level characters, where XP becomes essentially a bennie point system and advancement becomes more open-ended. As a result, several characters now roll with large bonuses on many rolls, which can take some of the fun out. I began tweaking things.

For a bit of background, DW offers three grades of result: a miss/fail (6- from dice+mods), partial success (7-9), or full success (10+). I have altered this by adding a new grade, which I call "superlative" success, where full success is now 10-12 and superlative is 13+. A superlative success doesn't just give you what you want, it actually adds unexpected advantages, unveils hidden information, or otherwise makes things Just Better. This is...not as easy as it sounds. Some things it works cleanly, e.g. if full success still forces you to only choose 3 things from a list of 5, then superlative success gives you the whole list. But others, especially Discern Realities, were more of a challenge, but I've found something I think works.

I also modified the Undertake a Perilous Journey roll, expanding it in a way that makes sense for our game and (if you'll forgive me patting myself on the back) actually manages to make sense as a new consideration that wasn't relevant before the characters became Legendary. Specifically, the standard Perilous Journeys require people to fill three roles: Scout (prevents you getting jumped by baddies), Trailblazer (navigator/orienteering guy, makes sure you don't get lost/take too long), and Quartermaster (logistics person, makes sure you have enough to eat and resources to get to where you're going). Due to the party makeup, the players were acing all three roles consistently. I added a new, fourth role: Trickster (still unsure about the name), whose job is to conceal the party's movements from anyone who might be tracking them. In the past, this wasn't a concern, because the party wasn't a big enough deal for people to track them most of the time. Now, however, they have Big Secrets and plenty of reasons for Bad Guys to tail them and monitor their movements. Choosing to ignore the Trickster role is less directly dangerous than the other two, but has potential long-term risks, appropriate for a high-level game.
 
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I sometimes don't call for a roll because it will automatically succeed. Sometimes I call for a roll because they may get more information or get the task done more quickly.

Conversely I call for rolls because I don't want the players to know the roll has no effect. Apparently this is borderline blasphemy, but if someone indicates they're doing an insight check to detect if someone is lying I'll ask them to roll. If the insight is lower than the NPCs deception or the NPC is not trying to be deceptive.

In other words the role of rolling is that it should be consequential to the game. That can happen many ways. Not revealing information to a player that the PC should not know, seeing if they can achieve more than expected, adding an air of mystery.

Ultimately though it's more about making the game fun, not following some hypothetical"correct" way of playing
 

We use mostly "ignoring the dice" because we like logical actions to have logical consequences, and rolls slow down the game, but sometimes on or our DMs will call for a roll for a "quality" of result, which is something that lots of RPGs have but D&D has consistently ignored.
 


I've noticed that my players will roll without me asking - for example, "I'm going to make an arcana check to know something about X" rolls - tells me the result. Which I have no problems with. It's active on the players part, doesn't really take any time and, even if the roll doesn't really matter (success was guaranteed, or there was no consequence of failure) everyone comes out happy.
If the player simply declared they’re going to make an arcana check to know something about X, that doesn’t give me enough information to determine if the roll matters. I can’t know if success is guaranteed or there’s a consequence of failure when I don’t know what the character is actually doing in the fiction.
My advice would be to encourage your players to roll without asking. They know their characters, they know the rules of the game. Let them do it. I try to climb this wall, 15, do I climb it - is to me a perfectly fine way of doing things.
Perfectly fine for you, sure. Wouldn’t work for me, for the reason I explained above, among others.
Then again, I always encourage DM's to dump as much workload as possible off onto the players.
This is the opposite of dumping the workload on to the players. Calling for a check is trivially easy. Establishing what the character is doing in the fiction that the check is being used to determine the outcome of is… well, it’s not hard either, but it’s more work than simply calling for a roll based on what the player established their own character is doing (and more work still than not calling for a roll because what the player established their character is doing has no possibility of or consequence for failure). Moreover, it puts me in the position of having to narrate what a player’s character is doing, which is a line I prefer not to cross.
 

Absolutely. If there are multiple plausible outcomes, and the players will enjoy rolling, I establish the possible outcomes and ask for a roll.
Would not”multiple plausible outcomes” constitute a consequence for failure - i.e. getting one outcome instead of another?
 


I like the idea that if you are sufficiently skilled, the roll determines whether you a) succeed, or b) succeed and get a bonus. That way, the roll is still consequential even though the chance of failure is nil.
I usually prefer progress combined with a setback, but this is the same concept, just with more generally positive outcomes, and I’m all for it.
 

Would not”multiple plausible outcomes” constitute a consequence for failure - i.e. getting one outcome instead of another?
Eh, I think everyone means “consequence other than just not getting anything special from the situation” in these discussions.

Sometimes all the possible outcomes are success, with different details, or moving the story in slightly different directions, helping inform future “consequence” elements like an “unnecessary” Persuasion check helping inform how people at court view the characters involved in that check, and color their reactions later on, or even adding weight to one side of a decision about an NPCs future and what path they will take in the future.

They can also be used to add characterization for PCs and NPCs, to establish social dynamics, and other forms of soft influence on the game.
 

Moreover, it puts me in the position of having to narrate what a player’s character is doing, which is a line I prefer not to cross.
Oh, fair enough. I have no problems doing that though.

I rolled a 15 on my arcana check, what do I know about this monster?

Me: (looking at the monster and figuring, yup, that's good enough) You know X, Y and Z.

Player: I climb up the wall, 15 Athletics.

Me: You scramble up the wall with ease.

It helps that pretty much my entire group also DM's other games, or has in the past, so, they all know the drill. And, no one is too fussed about this sort of thing. Like I said, I much, much prefer, "I search the room, Investigate X" than, "I look around the room... pause for me to tell them to make the roll that they know they're going to make 99% of the time anyway... roll... pause while I tell them the result... move on."

I just find the notion that you can't understand what the player wants from context frankly baffling. It's not like we're all new DM's who've never played before. You know exactly what the player is trying to achieve most of the time, and, if I don't, I'll just ask.
 

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