Roll it back just one second!

Nevvur

Explorer
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.

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"

or

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.

Do you let Jon cast guidance? Do you let Bob gain advantange from Tom's help? If so, does Bob roll an additional d20, or does he roll a new pair of d20s? Do you first look at the result of the current die roll to see if a bonus or advantage would even make a difference? Or perhaps you expect your players to be on their toes for such opportunities, and it's too late once the die is cast and the total declared?
 
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Case 1) is easy to resolve for me. Just tell the player that the 1st attack finished off the ogre and have them choose a new target for their 2nd attack and reroll (letting them use the same roll is too easy to meta-game).

Case 2) is trickier, and, unfortunately, I think the answer is "it depends." Sometimes the players are trying to game the system, sometimes they're not. You have to judge each case individually.
 

Case 1: If the player rolls his attacks together, then they both attack the ogre. If the second is wasted it is wasted. This has happened, and I haven't gotten any complaint about it.

Case 2: I would let John cast guidance. I wouldn't have a problem with Tom in general, but I don't think I would grant advantage for "double talking" in the first place. If I did let it work, I would just roll a second d20.
 

Anything that speeds up the game should be encouraged. To that end, if something they did to speed up the game needs to be walked back because it was surprisingly unnecessary, I allow it. This includes things like retroactive Guidance, the Help action, etc...

If I see someone I think is abusing the situation for an unintended benefit, I'll tell them to knock it off. If they persist, my game table doesn't have room for them - although I've only kicked out 2 players from my games between 1979 and the present.
 

In Case 1 I would let the player move to a second target - having said this I have never had a player roll 2 hits at once.

In Case 2 with the sneaking Rogue I would allow guidance to be cast as the interaction with any NPCs etc has not started, as the character is about to set off, where in the case of the guard the interaction is underway so how the players react would be what happens (there are always exceptions of course).
 

For Case 1, I do ask that things be rolled sequentially. It's of benefit to the player to do so anyway. I get no pushback on this.

For Case 2, it depends. Generally once the roll happens, the result stands. But when I'm playing online, I do permit certain reasonable allowances for delays caused by not being able to jump in as quickly as at a table.
 

Case 1) Speeding up combat is good, I'm not going to punish my characters for doing what makes the game go faster. Especially when you have things like higher level dual weapon fighters action surging. Just have different color dice and follow a standard sequence (in order: red, white, blue, etc).

Case 2) Generally no. There may be some abilities/spells that let you do this (I don't remember off the top of my head) but if you want to do guidance it has to be before the action happens. In some rare cases I'll allow a wisdom/intelligence check.
 

Case 2 is why Guidance can be a bit of a pain in actual play. Logically, they should be using it whenever they can, and that's most of the time. So do you have the player call it out every single time, or come to an arrangement where the group apply it automatically where possible? Even then you're going to hit edge cases where it's not clear whether it would be applicable.

For the assisted check example, it's a tough call. If Tom had rolled a natural 20, would Bob still be insisting upon retroactively helping him, or would he have his character getting on with something else instead? In the end you have to go with your gut and make the ruling that feels right at the time.
 

In my games, I let the players know the general health of a creature. It still looks healthy (>50%), looks bloodied (=<50%), doesn't have much left (~10%), or is critical (<10 how). So players have a pretty good idea of when it's safe to roll all of their attacks, or when they should roll sequentially. Since, when not rolling sequentially, we tend to roll the damage at the same time, extra damage is wasted (though I'll give it a cool description).

In the second case, I'd allow it. Things resolve much faster at the table than in game time. Presumably, the rogue let's the group know that he's going to scout ahead before sneaking off, even if it's not outright stated as such. Therefore, the cleric would have a chance to cast the spell first.

In the case of the guard, I'd sort-of allow it but require the assisting player to roll their own check. After all, that plan could easily backfire, with them contradicting each other's stories.
 

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.
Personally, I’d just roll with both attacks hitting the Ogre, and I wouldn’t make a big deal of narrating him Ready being dead by the time the second attack hits. It was the player’s choice to roll both attacks at once rather than waiting to see if the first attack hit. I can see why others might just tell the player that he dies after the first hit and give him the second attack back, but personally I’d rather just narrate the results and move on.

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"
”Ok, Bob, if you want to use that d4 you can roll it now and add it to your 15, or use it on a later roll if you like.”

Reasoning: this one is my fault for not offering the other players the opportunity to buff Bob’s character before asking for Bob’s roll. I’m not going to deprive Bob of a +1d4 because I was in too much of a hurry.

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."
”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. In fact, based on his description, it sounds like he and Bob have different goals and approaches, so I don’t feel giving Bob Advantage would be an appropriate way to resolve Tom’s action. Tom should make a roll of his own to see if his approach succeeds in achieving his goal, and it should have Disadvantage because the conflicting stories from Bob and Tom are going to set the guard on edge.

Now, assuming I had determined that Advantage to Bob’s roll was an appropriate way to resolve Tom’s action, I would have instead said, “Ok Bob, go ahead and make that second roll since I didn’t give Tom the opportunity to say that before you rolled. Tom, please remember just to describe your action, I’ll tell you what you need to roll to resolve it.”

Reasoning: this one is my fault again. I should have asked the other players if they wanted to say anything first before asking for Bob’s roll. I would want to verbally acknowledge my mistake, and also gently remind Tom to let me determine how to resolve actions.
 

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