Take lock picking for example. To pick a lock in 5e, the books explain that the character makes an ability check and applies their proficiency bonus from the tool (thieves' tools in this case). I call this a tool check for simplicity.
If the player is in a safe, comfortable place and they are attempting to pick a lock (let's say a wooden strong box they found on their last adventure), and they have all the time in the world, they successfully pick it. They just do. No rolling. Why? Because they will eventually get it open.
What if the player is trying to open that same locked strong box in a dungeon with dangerous random encounters? Then every attempt costs time. Lost time in a dungeon means torches burn away, light spells expire (not that this matters in 5e in particular), and there are chances of a wandering monster interrupting the distracted character. The DM can call for a roll here. On a failure, time passes, resources dwindle, danger approaches.
Tangent - What do the Rules Forbid and Permit?
What if the character doesn't have proficiency with a tool?
The way 5e is written, 5e very rarely, almost never states what is not permitted. It almost always states what is permitted. I think this is by design. If so, this is good to know about the books because it helps us understand them better.
If you don't have proficiency, RAW, you simple can't apply the proficiency bonus to an ability check. The rules don't state that lacking proficiency forbids characters from attempting actions or using tools.
The only instance I can find in the core books that forbid a player from attempting an action without the right proficiency is DMG, page 102, under Locked Doors, "...doing so requires thieves' tools and proficiency in their use." This appears to be an inconsistency in the game's instruction and possibly due to an oversight.
How Difficult is an Action
D&D 5e gives DMs instruction about choosing a difficulty class (DC) from pages 238 to 239. Let's look at some.
- Quote: "It's your (the DM's) job to choose a difficulty class for an ability check or saving throw when a rule or adventure doesn't give you one. Sometimes you'll want to change such established DCs."
I read this to mean that the GM may always choose the difficulty class when they believe it's appropriate. If you're running a published adventure or a monster from the monster manual, you may change an established DC.
- Quote: "Think of how difficult a task is and then pick the associated DC from the Typical DCs table."
This means the DM decides how difficult a task is, and DMs do so using a scale that the game gives:
- Very Easy (DC 5)
- Easy (DC 10)
- Moderate (DC 15)
- Hard (DC 20)
- Very Hard (DC 25)
- Nearly Impossible (DC 30)
The DMG is written like it's advising you to pick a word, not a number. It says "...think of how difficult a task is, and then pick the associated DC from the...table." The number is associated with the word. It tells you your game can be completely functional if you stick with Easy (10), Medium (15), Hard (20).
Objective vs Subjective Difficulty?
Objective difficulty means standardizing DCs for everything with the expectation that the DM is intended to use them. Subjective difficulty means that the difficulty is subjective to an individual's feeling or belief. As previously discussed, the DM chooses DCs when none are provided, and the DM may change a DC established by an adventure or rule.
When you choose a DC when there is none, you are evaluating the action yourself. When you evaluate an established DC, you may change it. The game trusts you and gives you the authority to do this.
Changing Established Game Content
Remember my tangent about how D&D 5e is written to be permissive rather than restrictive?
Page 6 of the Monster Manual has a sidebar that reads "Feel free to tweak an existing creature to make it something more useful to you." Then it refers you to the DMG. Page 273 on the DMG has a Section Creating a Monster and a subsection Modifying a Monster.
You're given guidance here, but no restrictions. The pattern in 5e is that the books repeatedly give guidance, examples, and procedures, but then returns authority to the DM.
This should go without saying, but the author's intent is not anything goes. Remember RAI? The DMG reminds you that changes to statistics change the monster's CR. The game still intends for you to adhere to their Challenge Ratings (CR) system. It gives you tables and explanations to understand the design logic of D&D 5e.
If You Fail, Do You Fail Forever?
Can players repeat failed actions? Short answer: Some but not all.
DMG, page 237, under Ability Checks, ability checks are defined as a test to determine whether a character succeeds at a task. That's it. One task. In fact, this section of the DMG explicitly tells you that players can repeat a task, and to save table time, you can assume that a player who spends ten times as long on the task automatically succeeds.
Note that this portion of the book resolves some situation in your game where players want to repeat checks ad nauseum. This works for things like picking locks or tying knots unless the character is in a rush, under pressure, or in danger.
This section of the DMG also says that no amount of repeated checks can turn an impossible task into a possible task, and, in some cases, failing a check makes it impossible to make the same check to do the same thing. It also says that you can decide if initial failure makes repeated checks more difficult.
How do you know which checks can't be repeated?
Short answer: DM judgment.
How do you judge this? Consider that this is not just a game, it's also a fiction and a setting. Ask yourself what makes sense within the fiction and the setting?
Let's say a player wants to pick a lock in a dungeon. As already discussed, you may call for a roll. If you fail to pick a lock in real life, you simply fail. The lock doesn't break. Neither does the tool. This action can be repeated.
Let's say a player wants to disarm a trap in a dungeon. On a failure, the trap springs. That means the player logically gets one try. The action cannot be repeated unless the trap is reset and needs to disarmed again.
Were you to tell a player no they can't repeat an action, consider you justification. Would you tell them that they can't repeat an action because it's already been done? What changed that prevents them from repeating it? Would you tell them "that's the way the game is played." That justification would be arbitrary and contrived, and the player would justifiably not be satisfied by this ruling.
How about making a knowledge check? Note that the PHB uses the word "recall" rather than "possess" in the descriptions of knowledge skills (arcana, history, nature, religion). Meaning we roll int (knowledge) checks to determine if a character recalls knowledge, not whether a character possesses knowledge. This allows for a possibility that any knowledge can be possessed by any player character, but success of recall varies.
The definition of an ability check (DMG page 237) is for a task, therefore recalling knowledge is a task. I would rule that knowledge is one of those cases where failing a check makes it impossible to make the same check to do the same thing as previously discussed. In other words, failing a knowledge check means you can't recall the knowledge until you try something different or something within the fiction changes. Maybe you hear a new rumor or piece of lore and you can justify "maybe this jogs my memory. I try to recall knowledge." That works for me.
How about for repeated speech checks? Read your DMG pages 244-245.
- Quote: "Once a charisma check has been made, further attempts might be fruitless or run the risk of upsetting...the subject creature potentially shifting its attitude...Use your best judgement."
I think that portion "Use your best judgement" is the game giving you its trust.
Is the Character Aware That They Failed?
Have you had this experience? "I roll stealth. Uh oh, natural 1. Guess I'm detected!"
First, that is called metagame thinking or metagaming. The player is aware of the concept of an ability check, a die roll, and a natural 1, but the character isn't. Reference DMG page 235 Metagame Thinking.
Second, when / how does the character become aware that they failed a task? I would also like to point out that page 237 of the DMG defines ability checks as a means to determine success or failure for a task. This definition does not state whether or not the character is aware of success or failure.
So how does a character know if / when they failed (if it's not obvious)?
We're talking about the moment in the game when the outcome of a task is revealed.
Option 1. One preferred way to handle this is to hide the rolls from the players; The character finds out when the player finds out. Make a roll when the player declares an action and save that roll for when (or if) it's needed.
Option 2. Consider this: As a DM you don't just decide whether a roll is needed for a task, but also what moment during the game to call for a roll. If a player says "I sneak", you don't have to call for a roll until there's someone or something that can perceive the player character. Then either call for an opposed roll (stealth vs perception), call for a stealth roll vs a DC, or use passive skills, or whatever.
When the failed roll becomes relevant within the game, then you reveal consequences. That's how the character finds out (if the result is not obvious).
Deciding Consequences
The game does not prescribe consequences (outcomes) for success or failure of every action. Sometimes failure means failure, but what happens on a failure is based on the context of that moment in your game. The consequences ought to be what would logically happen on a success for failure within the context of the fiction or setting.
Avoid punitive consequences or gotcha's.
Page 174 of the PHB, the last sentence under Ability Checks reads "...failure, which means the character...makes no progress towards the objective or makes progress combined with a setback determined by the GM."
Did you miss it? RAW, failing an ability check doesn't automatically mean nothing happens or that no progress is made.
Page 242 of the DMG, under Resolution and Consequences, it reads "You (the DM) determine the consequences of attack rolls, ability checks, and saving throws. In most cases, doing so is straightforward...As a DM, you have a variety of...approaches...to make things less black and white." It then lists several options:
- Success at a Cost
- Degrees of Failure
- Critical Success or Failure
These is a core rule, not an optional one, not a variant. I've never played with these rules. I've never heard anyone talk about degrees of failure or succeeding at a cost in 5e. It's very oddly overlooked in discussion about D&D 5e.
Trusting the DM - DM Resolutions and Descriptions
The GM is supposed to be fair, neutral, and consistent. You're not going easy on the players or making the game difficult for them. Arbitrary, contrived, inconsistent, or capricious rulings diminish trust in the GM.
Once you decide how to resolve an action, you describe it. Your DM descriptions are your players feedback about their actions in the world. DM descriptions need to be objective and clear. If success or failure is supposed to be a mystery until the consequences are revealed, that's fine if it's understood; otherwise, the DMs descriptions should not be ambiguous. "The knot is secure" or "The knot is loose", not "The knot looks good to you" or "You think the knot is secure". Ambiguous descriptions lead to players attempting to repeat actions just to make sure they're safe. Ambiguous descriptions lead to players being suspicious of DM descriptions. That's not cooperative or collaborative play.
Conclusion
Many new DMs approach the game as though the books are trying to provide complete procedures for every situation; however, D&D 5e expects DMs to exercise judgment far more often than they may realize. Honestly, I don't think D&D 5e is beginner friendly, but hopefully you now know that the rules and dice do not determine the game, the GM determines the game with the rules and dice as tools. The rules do not replace the DM's judgment, they support it.
I spent about 10 hours on this post. After writing a game of my own (Bright Dark 3d6 Role-Playing Game), I have a new appreciation for the amount of work that goes into writing a rule book, and by writing this post, I have a newfound respect for the 5e designers and the 5e game itself.
Related: If you're interested in reading more rules that might change the way you think about D&D 5e, I wrote The Authority of the GM / DM which lists many rules across the three core rule books with an explanation or interpretation.