Roll it back just one second!

Multiple attacks on one creature: I'm more of the mindset to encourage players to explain their action or bonus action (in order if dependent) before rolling for stuff. This means the players need enough info about the enemies to make good decisions, but also means there is that uncertainty if one opponent is near death and how lucky they feel their rolls are. Most of the time it pays to be over zealous with a dangerous monster and the policy adds tension due to that little bit of uncertainty.
(my personal preference on how to play)

Once a player rolls for something, and nobody pipes up while the roll is in progress, then the outcome is final on that roll. Even a,".... wait, wait, wait." or *finger held up*"Ummm" is good enough, so long as the die is either still rolling or the player trying to modify the results is not looking at it (looking at ceiling, blocking vision, etc.). I would then try to see if we went too fast for a roll or if the player was just a bit behind about thinking what to do (rectify for future).

I do not like
"I look around, trying to see if there are any hidden evil shrubberies"
*Entire party knows this character has a +6 to perception, one of the best among them*
"Roll for perception"
*clatter*..... *hisses through teeth* *looks at sheet*
"8"
"Actually, I was going to use my bardic inspiration"

(no modifiers unless good faith effort to not know what the roll is while explaining what you want to do)
 

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DM style questions. Just looking for insights and justifications on different approaches.

Case 1)

I've seen players and DMs alike resolve actions simultaneously when, by RAW, it should all be sequential. For example, a player with Extra Attack will announce, "I'm going to take a couple swings at the Ogre," then roll 2d20. It's expedient, I get that, especially for a big bag of meat like an ogre. Let's say both attacks hit, but you only needed one hit to KO him. Do you let the warrior move and keep the second attack roll to apply against another target? Ask for a reroll? Tell him the second attack was apparently spent hacking the monster into red mist?

At my tables, I enforce sequential resolution so it's not an issue. However, I'm a player at a table where some of the players do simultaneous attacks. The DM rides with it, and while it's not a deal breaker for me, it always bugs me.
In your example, the attack would "go to waste". But since the player is rolling their attacks at the same time, and then their damage at the same time, I only report the outcome of the total damage. "Your quick succession of attacks finish the beast off!" Does it really matter if the second attack went to waste? I generally try to avoid reporting HP numbers to my players. "He looks healthy!" "He looks a little roughed up." "He looks pretty bloody." "He's barely hanging in there."

Typically I will frame actions in "blocks". The player goes, declares what he does, who he does it to, and how much of an effect it produces. I will then respond to that and then provide a response, if there is one. IMO, a "turn" is so fast you may not know if it was your first punch that finished the beast or your second, or third. It's when you pause that you'll see the outcome.

Case 2)

DM: "Okay Bob, you said you wanted to sneak ahead and scout. Give me a Dexterity stealth roll."
Bob: Rolls, "15 total."
Jon: "Oh, I wanted to use Guidance before he snuck off"
Usually, I'll have Bob and Jon roll a quick initiative check. If Bob wins, sorry Jon, he snuck off before you could cast your spell. If Jon wins, Jon notices Bob before he leaves and casts the spell, and then I make Bob re-roll. Could be better...could be worse. That's a risk they'll have to take, otherwise I'll run the system as "Too late Jon." every time.

DM: "A guard turns the corner unexpectedly and looks at the two of you sternly. You and he all know you're not supposed to be in this part of the palace."
Bob: "I make up a story about getting lost."
DM: "Roll Charisma deception."
Bob: Rolls, "5 total"
Tom: "Hold on, I'm double-talking the guard to throw him off balance, granting advantage to Bob's roll."

In both cases, we're looking at the rapid mechanical resolution of an action before the other player got a chance to announce he wanted to render aid.
Same answer. Tom needs to show his PC was quicker than Bobs PCs mouth. If they don't like it, they can play the alternative system of "Too bad, so sad."
 

”Please just tell me what your character is doing, I’ll determine how best to resolve the action. I’m hearing that you want to confuse the guard by double-talking him?”
(assuming the Tom responds in the affirmative)
“Ok, please make a Charisma check with disadvantage. Add your Proficiency bonus if you’re trained in Deception.”

Reasoning: Tom’s role is to describe his character’s actions, not to choose which mechanics to use to resolve those actions. It’s not his decision whether or not his double-speak would give Bob Advantage.

Wait a second. Tom calls out using the standard Help action, giving you a narrative of what his character is doing, and you not only disallow it but you make up some penalized action in it's place?

Heck no.

Having a player helping moving things along by giving the game mechanics result as well as his narration is good play.
 

Wait a second. Tom calls out using the standard Help action, giving you a narrative of what his character is doing, and you not only disallow it but you make up some penalized action in it's place?

Heck no.

Having a player helping moving things along by giving the game mechanics result as well as his narration is good play.

Well, the help action is really for when you are in combat. Here you would just use the "working together" rules. They call out that working together is only productive in the right kind of task. I think it is fair if the DM wants you to narrate how you are helping in order to make that decision. I probably wouldn't require that myself though.

At my table I imagine this might go:
Bob: "I make up a story about getting lost."
DM: "Roll Charisma deception."
Bob: Rolls, "5 total... the guard looks skeptical"
Tom: "Whoops, let me chime in and back up Bob's story"
DM: "OK" Rolls another die, "That gives a 12. He seems convinced."

In my head that second die would be the advantage die, but I wouldn't feel any need to describe it that way at the table.

That would all be fine, but it would probably be more fun if the players opted to roleplay the interaction :)
 

Thanks to everyone who has responded so far. I do want to clarify that I offer up examples illustrating a concept in order to dissect the concept, not the illustration. I'm aware there are unaccounted variables that can turn them into automatic "It depends" rulings. No complaints on how anyone has answered the questions put forth. Some of them have been enlightening, others a little a surprising.
 

I'm with you on sequential actions. My group (when we played IRL) used to roll attack and damage simultaneously to save time. If an attack would/might kill an opponent I'll tell them to wait a moment while I do the math. If a player already rolled, it got re-rolled. Now that we play in Roll20, the macros make it very fast.

As for case 2, I generally don't call for the roll until absolutely necessary. In the first example, likely guidance wouldn't help the roll, since a minute probably already passed before the check was made. In the second case, I would RP out the situation, and once I needed to have the guard make a decision, I would call for the roll. If the other player never said anything, then too bad, because they don't get to help.
 


Wait a second. Tom calls out using the standard Help action, giving you a narrative of what his character is doing, and you not only disallow it but you make up some penalized action in it's place?
The help action is specifically an action in combat. Outside of combat, you don’t pick Actions from a list. You describe what your character is doing, and the DM adjudicates the results, possibly requesting a check or other dice roll to resolve uncertainty in the outcome.

Having a player helping moving things along by giving the game mechanics result as well as his narration is good play.
Nope. That’s a 30+ page argument I am absolutely not interested in having again.
 

The help action is specifically an action in combat. Outside of combat, you don’t pick Actions from a list. You describe what your character is doing, and the DM adjudicates the results, possibly requesting a check or other dice roll to resolve uncertainty in the outcome.

Right, outside of combat, it's "Working Together," provided the task is one that the character offering help could attempt alone and when, in the judgment of the DM, such assistance would actually be productive.
 

Right, outside of combat, it's "Working Together," provided the task is one that the character offering help could attempt alone and when, in the judgment of the DM, such assistance would actually be productive.

Precisely. And in my judgment, “double-talking to throw the guard off-balance” would absolutely not be productive to the goal of convincing the guard of Bob’s story. Ergo, it would not grant Bob Advantage. However, the outcome of Tom’s action is uncertain- does his double-talk throw the guard off-balance or not? But because Bob just gave an unconvincing story with his roll of 4, the guard would likely be suspicious of Tom’s doublespeak, hence the Disadvantage.
 

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