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


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Thanks I missed this. I am running Flames of the Falcon for Greyhawk with 2024 rules and converting on the fly. I normally don't have a problem but this module trilogy is presented a bit weird.
 


To add to what @Azzy quoted above (which is derived from the 2014 rules, DMG p237):
DMG 2024 (p 28) said:

Trying Again
Sometimes a character fails an ability check and the player wants to try again. In many cases, failing an ability check makes it impossible to attempt the same thing again. For some tasks, however, the only consequence of failure is the time it takes to attempt the task again. For example, failing a Dexterity check to pick a lock on a treasure chest doesn't mean the character can't try again, but each attempt might take a minute.

If failure has no consequences and a character can try and try again, you can skip the ability check and just tell the player how long the task takes. Alternatively, you can call for a single ability check and use the result to determine how long it takes for the character to complete the task.

A key to avoiding the whole trying again cycle... whether the same PC or various party members is to heed this advice regarding ability checks in the DMG:

"Only call for a roll if there is a meaningful consequence for failure." 2014 p237
"The DM and the rules often call for an ability check when a creature attempts something other than an attack that has a chance of meaningful failure. When the outcome is uncertain and narratively interesting, the dice determine the result." 2024 p10

If a player wants to risk accumulating consequences for their PC/party with multiple failed attempts, well, that's their prerogative.
 

If a task can be tried again and again until it succeeds without any costs or consequences - don't let them roll, just let them succeed and be done with it.

I usually let them reroll, but each attempt costs time and time matters in most of my games. There are also other consequences for failure. For example attempting to open a door could be accidentally too loud and guards come to see what causes a ruckus.
 

Is it in the rules anywhere? Or is it up to the DM?
It is task dependent. Failing while climbing a cliff, especially if it's a cumulative skill challenge, can be dangerous. Failing to persuade someone might make it impossible for them to trust you again in that moment. Heck, even when failing to pick a lock the first time, I have seen DMs say, "You tried, but it just eludes you. It could be the lighting, the rust on the lock, or something is jammed in it. But you can't pick it." And therefore, negate any future attempt in that specific setting. I don't see any problem with this.

I personally like two standards when dealing with skill checks: Some skill checks require you to have proficiency before attempting, and consequences, however minor, should be the result of a failure. The reason for the latter is, there are a host of spells, class abilities, and species-oriented abilities that help or negate skill checks. So, when the exploration pillar of the game does appear, it should have a clear purpose, a natural consequence, and an alternative if the skill check is needed to continue the plot.

In the end, the skills are so broad, that their specificity is what matters - a sometimes yes, sometimes no situation.
 

It is task dependent. Failing while climbing a cliff, especially if it's a cumulative skill challenge, can be dangerous. Failing to persuade someone might make it impossible for them to trust you again in that moment. Heck, even when failing to pick a lock the first time, I have seen DMs say, "You tried, but it just eludes you. It could be the lighting, the rust on the lock, or something is jammed in it. But you can't pick it." And therefore, negate any future attempt in that specific setting. I don't see any problem with this.

I personally like two standards when dealing with skill checks: Some skill checks require you to have proficiency before attempting, and consequences, however minor, should be the result of a failure. The reason for the latter is, there are a host of spells, class abilities, and species-oriented abilities that help or negate skill checks. So, when the exploration pillar of the game does appear, it should have a clear purpose, a natural consequence, and an alternative if the skill check is needed to continue the plot.

In the end, the skills are so broad, that their specificity is what matters - a sometimes yes, sometimes no situation.

Personally I like the flexibility. Let's say I have a cliff face or old half-ruined castle wall that is not terribly difficult to climb. Something that someone proficient in athletics likely won't fail. But if you really blow it then it's more dangerous. Fail by less than 5 climbing that not-very-steep cliff and you make it to the top, it just takes longer to get up. Fail by more than 5 and give me another check. Fail again and take 1d6 damage as you fall down 10 feet taking scrapes and strains as you go. Repeat until you get to the top or give up.

I'll be sure to describe what the characters perceive as the level of risk in these scenarios but I like that we can have a bit of wiggle room because to me it feels more realistic. Similar to how I handle lockpicking but when lockpicking there's no chance of harming yourself.
 

Personally I like the flexibility. Let's say I have a cliff face or old half-ruined castle wall that is not terribly difficult to climb. Something that someone proficient in athletics likely won't fail. But if you really blow it then it's more dangerous. Fail by less than 5 climbing that not-very-steep cliff and you make it to the top, it just takes longer to get up. Fail by more than 5 and give me another check. Fail again and take 1d6 damage as you fall down 10 feet taking scrapes and strains as you go. Repeat until you get to the top or give up.

I'll be sure to describe what the characters perceive as the level of risk in these scenarios but I like that we can have a bit of wiggle room because to me it feels more realistic. Similar to how I handle lockpicking but when lockpicking there's no chance of harming yourself.
Interesting. I am a much more of a success/failure type of DM. No gradients for me. It overcomplicates the game in my opinion. Also, I don't really like a whimsy DM as a player. What's the DC? 15? Cool. I rolled 14+2=16. Success. But I have seen it done in gradients, and it is really good for some DMs and players. No knock, just not my cup of tea.
For example, your castle wall. I might, as a DM, start by saying it's tough. You can only attempt it if you have proficiency in acrobatics or athletics. Maybe only you can spot the route up or can adjust your body enough to succeed on the first deadpoint maneuver. Then, if you succeed, you can coach others how to get up because you know the route, or you can help them by lowering a rope, or you can place pitons into the wall to help them. If they succeed, great. They can help others. If they fail, they take fall damage.
Of course, for this example, if I am requiring them to "scale the castle wall" I am going to build in one or two other ways into where they need to be. Alternative skill paths, to me, are key.
 

Interesting. I am a much more of a success/failure type of DM. No gradients for me. It overcomplicates the game in my opinion. Also, I don't really like a whimsy DM as a player. What's the DC? 15? Cool. I rolled 14+2=16. Success. But I have seen it done in gradients, and it is really good for some DMs and players. No knock, just not my cup of tea.
For example, your castle wall. I might, as a DM, start by saying it's tough. You can only attempt it if you have proficiency in acrobatics or athletics. Maybe only you can spot the route up or can adjust your body enough to succeed on the first deadpoint maneuver. Then, if you succeed, you can coach others how to get up because you know the route, or you can help them by lowering a rope, or you can place pitons into the wall to help them. If they succeed, great. They can help others. If they fail, they take fall damage.
Of course, for this example, if I am requiring them to "scale the castle wall" I am going to build in one or two other ways into where they need to be. Alternative skill paths, to me, are key.

It doesn't come up very often, but the DC for any check is always going to be a bit arbitrary isn't it? After all if I want to make a wall climbable I'm not going to make it an impervious sheer ice wall. So most of the time, even with a wall they really should be able to climb, there will be other options to achieve their goal.

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.
 

If a task can be tried again and again until it succeeds without any costs or consequences - don't let them roll, just let them succeed and be done with it.

I usually let them reroll, but each attempt costs time and time matters in most of my games. There are also other consequences for failure. For example attempting to open a door could be accidentally too loud and guards come to see what causes a ruckus.
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". Plus if they get the roll, on that impossible lock the first time, they are truly proving themselves legends in the fiction of the world.
 

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