D&D 5E (2014) Can you retry a failed skill check? How long?

I know I'd be a bad parent because my philosophy as a DM is "a skill check represents you trying your best: your best wasn't good enough". If you think you can get a 20 on that theives tools roll to unlock the door, then you shoulda thought of that before you rolled the dice the first time.

The only exception I'll make is if your "best" mechanically changes: if you're under the effect of a buff that changes your aptitude in that arena, or you've since leveled up and gotten better and more practiced at that skill.
 

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The main area where I have different DCs in mind is with knowledge checks. You may recognize a holy symbol of Set automatically, a DC 15 and you realize it's not the standard version you've seen before, a DC 20 and you recognize what's different about it and get an idea of what it implicates and so on.
Yes, I have written that into adventures for key knowledge checks. For example, a simple history success gives them x knowledge, but a hard history success gives them x + y knowledge, and an epic success grants them x + y + z knowledge. If you have the time to do it for adventures, I find it very beneficial.
 

my philosophy as a DM is "a skill check represents you trying your best: your best wasn't good enough".
I do something similar but with a variation: I say "The skill check represents your best attempt under the current circumstances. If you want to try again, you'll have to change something to give you different odds." Depending on what they come up with, I might give them a bonus to the second roll. (Saw this idea online somewhere, but I can't remember where now.)
 

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".
 

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".
The door doesn't get to try to force you open in return, unless it's a mimic.
 

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".

I'd be perfectly okay with people making multiple attempts to open a door if I think they have a chance to open it. The reasons I would ask for checks in that case is if I want to know how many times they slamming against the door in case someone might hear it or if there's some immediate time pressure.

If it's too difficult to open (and I may ask the highest number they can get if I'm not sure), I'll just let them know they do their best and the door doesn't give at all.
 

The door doesn't get to try to force you open in return, unless it's a mimic.
I'm not sure I understand why there's a difference. I mean, I get that you feel that there's a difference, and that you're not alone in thinking that.

To my mind, trying to climb a cliff when there's a risk of falling isn't much different than attacking someone who can hit you back if you fail to defeat them. There's a consequence for failure.

But combat is typically resolved with many rolls, and nobody thinks anything of it that some rolls fail. You keep at it or you die.

Then suddenly, with an ability check, you do get the "no, sorry, can't try again". Back in my AD&D days, I never gave this much thought. I was told that if I failed a Thieving skill check, I couldn't do it again until I leveled up. Fail a spell learn check? Get more Int.

Fail a Bend Bars/Lift Gates or an Open Doors check? Usually the same.

It wasn't until later, when I started playing characters with more Non-Weapon Proficiencies (and later skills) that I started to considering something was strange with that mindset. It makes sense for a computer game, but as most of the people I gamed with started caring more about "verisimilitude" and "the game making sense" (as dubious as that can be sometimes), I started pointing out that this sort of thing doesn't make much sense either.

"You fail to find the book you're looking for in the library." The DM said.

"Can I keep looking?"

"No, you just can't find it."

"Unless it's not there, I'll find it eventually, right?" I replied.

And I got pushback for asking these kinds of questions. Again, people do think there's a difference, but I don't really grok what that is.

I had some friends who were into LARP (I don't recall which one), and they would explain that, in the LARP they were part of, if you test an ability against a player or NPC, and failed, you weren't allowed to try again- it was now a known fact that they were better than you. So if you tried to punch a guy and he dodged, he'd continue to dodge every punch. So you had to switch to a weapon or give up.

I didn't quite get that either, since it eliminated luck, but then again, that's a diceless sort of game.

Sports teams have spent a lot of money on research as to why players perform better some days than others. Why the same batter, against the same pitcher, on the same field, can be "on fire" one game, but mediocre the next.

What people keep pointing out to me is that a skill check might not be one swing at bat. It might be three. Or an entire inning. Or an entire game. Or an entire series. And that on a long enough timeline, the results of a d20 will eventually end up average.

But it's not like passive scores are used in games like that. If I make a downtime check for something that happens over the course of a week, it could be one roll of a d20. Then the next time, even if nothing changes, well, the result can be wildly different.

A lot of DM's hated it during the 3.x/PF1e days when you could take 20. They felt you should always roll. They'd often deny you the opportunity (IME) not by stressing how long it took, but by saying "well, something can happen if you fail". Because that's all take 20 was modeling. It was a shortcut for retrying again and again until you got it right.

Because if you search a room, one would hope you eventually find what you're looking for (granted, I have met some oblivious people, but not being able to make the check in the first place, or not being able to take 20x as long is a real possibility sometimes).

And today, well, there have been a lot of arguments about passive Perception (as an example) and that it should never be invoked. It's not a floor, and you can't just walk around and expect to passively seen hidden things, even if your passive is through the roof (the arcane gyrations made to prevent Observant from doing anything useful that I've seen are wonders to behold).

Heck, when I pointed out that advantage/disadvantage raises and lowers passives, I remember being told (by people who had played 5e a lot longer than I had at that point) that I was smoking something, despite it being right in the PHB!

I can see that people want high stakes on rolls. They want the non-combat part of the game* to be pretty much pass/fail and move on. I just don't see why. Especially when most of the rolls that are being asked to make seem a bit pointless.

DC's are often inflated to the point that you'd have to be a Rogue with Expertise to hit them, checks can be proficiency gated, DM's will rule that you can't be Helped, they'll grumble about Guidance, but when the high level Fighter sneers at AC 19, well, that's just how the game is.

*Unless you can make an ability check in combat routinely. Like 2014 Grapple. Surely nobody would say that, having failed to Grapple someone once, you couldn't try again? Or free yourself from one?
 

There is something to a roll. Even for something like a lock pick. Players derive huge satisfaction from a good roll even if in my mind "the roll doesn't matter"
If they just can roll again until they succeed without any cost the roll doesnt matter, not just in my mind, but as a matter of fact. But when I know that the roll doesn't matter I don't even let them roll, so the players don't even know they could've had a huge satisfaction from a nat 20 or something like that. Let me rephrase that: I don't build locked doors in my adventure if I know they can reattempted several times without any cost and consequences. I only build locked doors when there is a chance of getting caught or other consequences.
 

I know I'd be a bad parent because my philosophy as a DM is "a skill check represents you trying your best: your best wasn't good enough"

I do something similar but with a variation: I say "The skill check represents your best attempt under the current circumstances. If you want to try again, you'll have to change something to give you different odds."
I never understood this. For the me best a character tries is represented by his ability score plus proficiency score. The dice represent the external circumstances, luck, the weather whatever. For me a character doesnt' need to change something or at least nothing meaningful. In case of opening a door I would be satisfied with "I try a different angle with my lockpicking tools", but IME for DMs with your style this would be NOT enough.

As I interpret it:
Static bonus: Character skills and training, what the character did in the past
Dice: Random circumstances the character cannot influence. (because a player literally cannot influence the dice)
ADV/DIS: Approach/Angle, what the character can influence right now.

So for me trying with a different approach can change if the roll is ADV, normal, or DIS, but theoretically they can attempt it again and again. Because rolling untill it is successfull is boring you need to have consequences/costs. For climbing or jumping over a chasm its easy and natural for most DMs: you fall.

But with more abstract challenges many DMs have problems to think of interesting consequences. But they don't want autowins so it get arbitrarly said: "no, you cannot attempt again" which for me sounds like a crutch / expedient solution for not designing an interesting challenge.
 

It's interesting that in the game, attacking an enemy and missing, but being allowed to attack again, even though the circumstances (your offense skill and their defense skill) are unchanged is perfectly cromulent, but trying to force open a door makes some people go "well, you gave it your best shot, but you can't open this door unless you come up with a better approach".
Let me start with what I said before. Each skill check is unique, and therefore, might not follow the same logic. But...

I would argue the bolded above is not true. Combat is dynamic. After missing your attack, there are other PCs attacking, there are possible NPCs attacking, there are also creatures attacking. On top of that, in most combats targets and PCs are moving. And in some combats, environments move or shift. Then there is the fact that the target might lose hp, get hurt, gain a condition, etc. All of that is very different from trying to break a door that does not move and made of the same material. (Not sure the door example is a good one, as most in here already said they allow multiple attempts.)
 

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