TLDR: My most experienced player (2 years) was trying to retrieve his stolen spellbook in a crowd. He cast sleep "on the merchant." I asked him to read the spell out loud (although I knew it was an area of effect), he did, then I asked him "so what point are you casting it on, the merchant?" He said "Yes, right on the merchant." It put the merchant and his teammate to sleep and almost put him, the caster, to sleep... as the guards were approaching. He got mad saying, "Why didn't you ask if I wanted to put my teammate and myself to sleep?" I told him, "I don't want to question your creativity or a scheme you were planning, I just wanted to confirm the mechanics of what you were doing."

Question: I know there is no bright-line rule or line in the sand, but how much "hand-holding" is appropriate for non-new players (2 years). Am I required to confirm the consequence of every action a player takes? (Eg. Someone fleeing who forgets to take disengage... do I always avoid opportunity attacks by telling the player... "Hey, you forgot to disengage... do you want to?"). I am rooting for my players but want to let them play the game... not me coach them. I'm not a coach. I also know that if when declaring their action I walk through the result with them, it creates the possibility for them to "fish" for what the "best" result is... rather than have that authentic action they took. It's like chess... once you declare your action... its your action. Now if someone is thinking out loud what they want to do... I'm not going to hold them to the first thing they say... they are thinking. But if you declare your action that's that, I would think.

Thanks for any input/thoughts!

Narrative (If you care to know):

Last night I had a session and the Party was approaching Baldur's Gate (lvl 2). I've played with this group for two years in a homebrew campaign but now we are playing Descent Into Avernus. As they approached, the rogue wanted to use his criminal contacts background to connect with a thief. They talk, he gets information on the town using Thieves Can't. I was really impressed and in the moment I wanted to convey to the Party that Baldur's gate is unsafe and dangerous (especially in the outer-city) while allowing the Rogue to "flex" with his connection to the thief.

The thief ends the conversation with, "Remember, this area is my turf, I run the jobs here. Good luck getting inside!". The other three players, including a wizard, were watching from afar at the rogue talk to the thief in the alley. I rolled a sleight of hand check (19) contested by both the Wizard's passive perception (15) and his roll (10)... and I tell the Wizard he detects his spellbook was stolen.

What I thought would happen would be the Rogue would tell the thief that the Players were with him and could he get/order the spellbook back (which he would have no problem). I wanted to reward the rogue for initiating his background and thieves can't by preventing the theft and the wizard being grateful to the rogue.

Instead, they freak out and the wizard rolls an investigation check to find the footprints immediately, the rogue rolls a survival check to track the footprints. I had them go in a circle around the building back to the alley where the Thief had been. They see the thief pawning the item at a merchant in the bazaar, then run off. The party runs up to the Merchant, assumes he's in on the scam without talking to him, and one of the players ignites a firebolt in her hand and tells him, "Give us the lantern! I'm counting to three, or else..."

The Merchant thinks he is being robbed, and tries to grab his cart of wares and run. They throw a firebolt searing his back. The Wizard then runs up and says, "I cast sleep on the merchant." The players are in a crowded bazaar and they are within 5-10 feet of the merchant. I ask the Wizard to read me the spell (I know its an AoE and he doesn't get to choose the creatures, but I want him to make sure he reads it). He reads it aloud and I say, "Ok, at what point are you casting the spell, on the Merchant?" He responds, "Right on the merchant."

I say ok, and it puts the Merchant to sleep, the teammate who cast firebolt to sleep, and almost puts him, the wizard, to sleep. I think he got upset and said, "well I would have cast it in an area where it would have only impacted the merchant... I wanted the spell on him meaning to effect him." I told him the players were kind of all around the Merchant, how would he have done that. He tells me he would have done it in the air so only an edge effected the Merchant. He then says, "I'm an intelligent wizard, its not reasonable to assume I would put myself to sleep." I told him, "I don't know what you are planning. I can only ask you mechanically what you are doing, which you did. I thought maybe you were going to try and deceive the approaching guards by having you all asleep when they arrive... I don't know... but I don't want to cut your creativity short."

First, I would, even with experienced players, drop hints, like: 'you know, that you are within the area of the spell if you do that? Are you sure?' Especially when the players are a bit in a panic situation, I would be generous with the mechanical discussion.

Second, this is just my gut feeling, if you expected the group's thief to solve the spellbook stealing more easily, did he really get the information in the scene he needed, in order to figure out, that the other thief did that?

Sounds a bit like your players did not get the hint the way you intended. It is just guessing, but maybe you did not inform the group's thief clear enough? 

First, I would, even with experienced players, drop hints, like: 'you know, that you are within the area of the spell if you do that? Are you sure?'

Yup or I would say "OK centering it on the merchant would give you this radius" and lay down a template or show them on a sketch or something.

It doesn't matter how experienced the player is. If he's not cast the Sleep spell before, which plenty of experienced players may not have, or hasn't cast it before in 5e, he may not know all the effects. Some spells say "creature" some say "all objects" some say "enemies" or "targets." Keeping which one says what straight is something even vets like Matt Colville and Matt Mercer can't do. And if you watch their streams with highly experienced players, the players are often confused on what the abilities of their characters do at higher levels. The rules are complex. No one can keep them all in their head. And the player might well have assumed you would know he only wanted to nip the edge of the radius onto the merchant.

I agree with the "Unless you say it, it doesn't happen" rule in general (kind of like the "touch/move" rule in Chess). But... this seems a little hardcore. It violates common sense that a wizard would knowingly cast his own sleep spell on someone and put himself in the radius by accident. The wizard class has a high INT requirement so -- even if the player is too dumb to realize it, the character wouldn't be.

I don't think there is ever a problem with saying something like "thats fine, just to confirm you know you are in the AOE, right?" and go from there. Even if you have a map in front of you sometimes distance can be difficult to judge.

Also, in my campaigns a few of my players characters often make character mistakes, not player mistakes. I had a player recently very nearly accidently kill another during some fantastic RP and I quickly asked "You both know that X could die if you do that, just to be sure" they both said yes so I let them proceed.

I don't think it breaks immersion to ask the question, you don't need to offer further advice or clariication unless they ask you for it.

While I feel it's cheesy to just cast the sleep on the whole party, I feel that it's equally cheesy to cast the spell in the air to just hit the merchant. It just seems like a bad spell to cast when you're in the area of effect.

Yes, casting sleep in that circumstance is a terrible idea because of its relatively indiscriminate nature. 

But the thing is, so much of D&D is open to DM ruling. So as DMs, one job we often have is to tell the players how we interpret spell rules. So it is only fair to tell a player if sleep is cast here, this is probably what will happen. The character would know how the world works, but the player may not.

I wouldn't just spring this on them. And I wouldn't be coy by asking "where are you centering the spell?" I would tell them why I want to know.

EDIT: Also, you say they are 2nd level. It's early in the campaign, right? So early on you can say things like, "OK, I will allow a retcon here, but in the future, know how the Sleep spell works and plan accordingly. There will be no more retcons." I promise the player will never screw this one up again.

Quote from RockRollDie >>

I don't think there is ever a problem with saying something like "thats fine, just to confirm you know you are in the AOE, right?" and go from there. Even if you have a map in front of you sometimes distance can be difficult to judge.

Also, in my campaigns a few of my players characters often make character mistakes, not player mistakes. I had a player recently very nearly accidently kill another during some fantastic RP and I quickly asked "You both know that X could die if you do that, just to be sure" they both said yes so I let them proceed.

I don't think it breaks immersion to ask the question, you don't need to offer further advice or clariication unless they ask you for it.

First, thanks to all for the feedback!

If the stakes were as high as killing another player, I would certainly bring up their express intended result. The risk in this case was being captured by Captain Zodge in the campaign who needs their help to root out Cultists... so I viewed it to be a non-lethal risk, they just got to choose how they came to interact with Captain Zodge pursuant to the campaign module (eg. simply approaching the gate and requesting entrance into the city in exchange for their services).

I thought that by having him link the spell into Roll20, reading it (he read the AoE and it was on a VTT where he could see exactly how close he was). The player is my twin brother who is an Engineer. I don't want to cross-examine him when he is declaring his action (I'm an attorney and I don't want to sound hyper-technical). I let him read it out loud to make sure he understood it and then asked again where he wanted to place it. I do also think there is a responsibility on the DM to analyze the perceived communication versus what may have actually been communicated (that's why I had him read it).

The feeling that I could tell him, "Hey, you know that you are in the aoe"... that's my point... how far do I hold a player's hand and when am I starting to play the game for them? Do I warn a player every time in the panic of a situation they are going to face an opportunity attack?

Again, its like if I'm watching two players play chess and caution them every time they are considering a move.

I know its a spectrum and I do not want to create a false dichotomy of all or nothing... absolute silence or hovering over the player's every decision... I guess I'm just trying to find where others would have fallen on that decision in the spectrum. Regardless, the underlying decision should be in the spirit of having the players enjoy the game... but part of the game is making mistakes and enjoying how to react/recover from things not going how you expected.

Thanks again for the feedback!

D&D is not chess. You all play together, DM and players. Stating consequences of actions and letting the player realize that is ok. 

The feeling that I could tell him, "Hey, you know that you are in the aoe"... that's my point... how far do I hold a player's hand and when am I starting to play the game for them? Do I warn a player every time in the panic of a situation they are going to face an opportunity attack?

You warn when it is reasonable.

For a new player, I would absolutely warn that they could face an opportunity attack. I would not say "you will," but rather, I would remind them that, as a general rule, under these circumstances it could give the other character an opportunity to attack them as a reaction. For a more experienced player, I'm not sure if I would do that -- I think it would depend on circumstances. Part of the unknown of the player is what the enemy's melee range is. Something that has a melee range of 10' would cause AOs in parts of the battle map where a smaller creature with less reach would not. THAT is something that must be found out by trial-and-error during the battle. Although I hate to invoke Critical Role for things because their way of doing this is not "the right" way, I happen to like how Mercer handles AO questions in that show. When one of his players (who have been playing with him for years) looks at the map and says, "If I move away from here will they get an attack of opportunity?" he will answer with, "They might. Try it and see." Which of course means, yeah, probably... but again, you can only know this by trial-and-error.

Spells, however -- a wizard should not have to do trial-and-error to find out how big the radius of his own spells are. Surely he wouldn't hit himself with his own AOE -- as a courtesy I would point this out.

Years ago a friend of mine said there are two primary models of DMing -- the DM as angry god, and the DM as the players' best friend. In my group, we always went with the best friend model. Be the players' best friend. This doesn't mean don't challenge them, or protect them from suffering realistic consequences of their characters' actions. But there is no reason as their best friend, you couldn't point out what those consequences will be FIRST, rather than letting them suffer them without realizing what was going to happen.

"He should have known." Maybe. But as his best friend, does that matter? What would his best friend have done?

Quote from Voras >>

D&D is not chess. You all play together, DM and players. Stating consequences of actions and letting the player realize that is ok. 

It isn't chess. And the DM is playing the game with their players, not playing the character with their players or for the players.

If an action is a 6 second moment in combat, do you go over consequences for 2-3 minutes allowing the Player to analyze  or let them make an authentic decision?

Here's a different example (Spoiler) IF YOU HAVE NOT SEEN Critical Role Season 1 up to Episode 97... Spoiler below

I keep the following in mind:  Players are not their characters.  Their real life stats do not match their characters.  If they are supposed to be particularly stupid/intelligent, charming/obnoxious, wise/foolish, I do NOT expect them to automatically do that.

If they fail to play stupid, obnoxious, foolish appropriately, I tend to ask them "Is X smart/charming/wise enough to do that?" when I am not sure if they are role-playing their weakness enough. 

Similarly, if their character is smarter/more charming/wiser than they are in real life, I have them roll Int/Cha/Wis checks and give them a hint if they make the roll.   They should not be punished for not having a 20 Int/Wis/Cha in real life.

But  I NEVER tell them no they can't say/do that.  Instead I let them get away with more when I think they are role-playing well, and get harsher/stricter if they are not.

Quote from BioWizard >>

The feeling that I could tell him, "Hey, you know that you are in the aoe"... that's my point... how far do I hold a player's hand and when am I starting to play the game for them? Do I warn a player every time in the panic of a situation they are going to face an opportunity attack?

 

You warn when it is reasonable.

...

 

Years ago a friend of mine said there are two primary models of DMing -- the DM as angry god, and the DM as the players' best friend. 

 

Even though I quoted only a portion of your response, I read the whole thing and really appreciate it. As a lawyer when I see "reasonable" i think subjective rather than objective... which is open to interpretation... which of course is why I ask the question because there isn't a bright line rule and sometimes its 'iffy".

Like I said in another response, I don't like or want to create a false dichotomy. The Angry God vs. Player's Best Friend is a dichotomy. I think there can be an in-between. I view (not that it is correct, just how I view it because its how I prefer it)... the DM is a neutral arbiter of the game/rules who is secretly rooting for you. 

I guess my hints are more subtle... aka "Hey could you reread that spell out loud for me?... Great, so tell me where you want that point again?" I'm not interfering, just giving them an opportunity to ask questions for clarification (which I would give if he asked) or be specific in their intent to their action.

Thank you again for your input!

Quote from Mog_Dracov >>

 

Similarly, if their character is smarter/more charming/wiser than they are in real life, I have them roll Int/Cha/Wis checks and give them a hint if they make the roll.   They should not be punished for not having a 20 Int/Wis/Cha in real life.

But  I NEVER tell them no they can't say/do that.  Instead I let them get away with more when I think they are role-playing well, and get harsher/stricter if they are not.

I REALLY LIKE THIS! Thank you. I think this is exactly what I was looking for. THANK YOU!

(Edit: Also, my brother/player is incredibly smart, but I get what you are saying... its almost like a passive intelligence or intelligence check to see how much you help them)

In this case, the question I have is - instead of saying things like "read the spell out loud" why didn't you just say what the effect would be? "If you cast it on a point centered on the merchant, the people in the AOE would be (whoever that would be - the merchant, the party, etc) - is that what you meant, or did you want to find a spot so that the merchant's the only one in the area?" 

I mean, that sounds like you were trying to get the player to realize that. But why didn't you just say it? 

Dunno, maybe in this crowded of a place it was impossible to cast sleep "on the merchant" (i.e. place the AOE so that the merchant and only the merchant was the one hit). But that's the kind of thing that's hard to communicate unless you say it directly, instead of hinting that something's wrong with the course of action the player's taking but not telling them what...

(For what it's worth, thinking about how my games have gone, when I'm playing theater of the mind combat, "I cast [AOE] on [enemies A B C]" has always been how people describe placing AOEs - sometimes they have to ask clarifying questions to understand exactly what enemies they can and can't target at the same time, but in the absence of a grid, that's always how the description ends up...)

When I do Theater of the Mind, players generally ask things like "How many bad guys can I get in the fireball?

And in response I say things like "Only 2, unless you are willing to include your ally the Rogue in which case you can get 3 plus the Rogue"

I think there can be an in-between. I view (not that it is correct, just how I view it because its how I prefer it)... the DM is a neutral arbiter of the game/rules who is secretly rooting for you. 

That's kinda the same thing as the DM as your best friend. The "secretly rooting for you" part gives it away. You put challenges in front of the players that you hope they'll overcome. And you work hard to make sure everyone has fun. That's what DM as best friend is. 

Now back to the matter at hand... as the players' best friend (and brother in this case) -- your goal isn't, or shouldn't be, to trick or deceive by lack of information or clarity, your players into doing something that, if their character had realized what they were doing, they wouldn't have done. Your goal should be to put all the relevant information the character would be able to know in front of the player, and let the player RP out the reaction to that information.

I think everyone needs to step away from the specific example. It's not wrong as a DM to want your players to make a decision without you needing to amend it. Sometimes it needs to happen though. The group I play in routinely reminds the DM if he forgets about a negative situation affecting one of our characters, and in return, he points out advantages or difficulties we should realize.

Now for the specific example with Sleep. This bothered me so much, I had to come up with a houserule to test. I can't count how many times someone has cast an AoE centered so specically and perfectly, to hit maximum enemies and no allies. It's been done by characters and monsters barely smart enough to judge individual threat potentials, let alone to employ superior strategic tactics. I am thinking whenever a character needs to be this specific about positioning an AoE, they need to save against there own spell DC for the spell  being cast. They always use their main casting stat for the purpose of checking against the DC regardless of what stat the spell save normally requires. If they fail this check by more than 5 points, every additional point is a target missed or an ally struck. Start at the focal point of the AoE and reposition it to reflect as closely as possible.

This might seem ridiculous to some people but, casting Sleep on one target that is completely surrounded would require a metagaming placement of the sphere so the bottom of it perfectly hits about head high and conveniently curves enough not to affect characters just 5 ft away. To me, this is ridiculous.

he group I play in routinely reminds the DM if he forgets about a negative situation affecting one of our characters, and in return, he points out advantages or difficulties we should realize.

This is how it should be. This is what happens when the DM and the players are each other's best friends.

casting Sleep on one target that is completely surrounded would require a metagaming placement of the sphere so the bottom of it perfectly hits about head high and conveniently curves enough to affect characters just 5 ft away. To me, this is ridiculous.

I see what you are saying. And in an IC-sense, I agree with you. However, not to the extent that I'd be willing to make up a house rule to deal with it. I feel like in such a case, again... we are all friend here (at the table or VTT). Can't we all agree that being this precise is a little unrealistic, and maybe ask the player to come up with a more reasonable choice for the character? Again, if we are friends and get along, and if the player is actually RPing, this would not be objectionable in the least.

Quote from Wtfdndad >>

Now for the specific example with Sleep. This bothered me so much, I had to come up with a houserule to test. I can't count how many times someone has cast an AoE centered so specically and perfectly, to hit maximum enemies and no allies. It's been done by characters and monsters barely smart enough to judge individual threat potentials, let alone to employ superior strategic tactics. I am thinking whenever a character needs to be this specific about positioning an AoE, they need to save against there own spell DC for the spell  being cast. They always use their main casting stat for the purpose of checking against the DC regardless of what stat the spell save normally requires. If they fail this check by more than 5 points, every additional point is a target missed or an ally struck. Start at the focal point of the AoE and reposition it to reflect as closely as possible.

This might seem ridiculous to some people but, casting Sleep on one target that is completely surrounded would require a metagaming placement of the sphere so the bottom of it perfectly hits about head high and conveniently curves enough not to affect characters just 5 ft away. To me, this is ridiculous.

I am trying to think of a similar idea. I don't like that in character you couldn't be precise as you can be looking from a bird's eye view on a grid. My thinking was similar in they do a stat check. E.g. wizard rolls INT and if it fails the DC then they roll a 1d4 and the area moves by 1or2 tiles north/east/south/west. With the implied rule that it happens every time they cast an AoE but in practice we only roll when it the movement would effect the outcome. 

While I can see your point, I don't feel that the player asking for an opportunity to allow their character to do max enemy enveloping damage with a superbly places AoE is out of line. Expecting it to be flawless every time is the problem.

Just like there is a solution to the guy that loves to range attack enemies engaged with allies(see below), I would have an optional rule for the guy who likes to AoE with possible Friendly Fire mishaps.

Hitting Cover

When a ranged attack misses a target that has cover, you can use this optional rule to determine whether the cover was struck by the attack.

First, determine whether the attack roll would have hit the protected target without the cover. If the attack roll falls within a range low enough to miss the target but high enough to strike the target if there had been no cover, the object used for cover is struck. If a creature is providing cover for the missed creature and the attack roll exceeds the AC of the covering creature, the covering creature is hit.