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In one of my last sessions, my players were about to begin their battle with the big bad of the story arc: a Hag who had taken over the body of the village herbalist and was quietly poisoning the residents with mushrooms.

While confronting the Hag, the party tried to get answers out of her, and the Sorcerer cast Hold Person. While holding her, the Sorcerer also rolled a 20 on an Intimidation check and told me what she said to intimidate the Hag. I couldn't think of any good reason that the Hag would be intimidated, as the body she had taken over wasn't hers, thus the Sorcerer's threats meant nothing. I told the Sorcerer that the Hag seemed to lose her composure a bit but ultimately wasn't shaken.

The Sorcerer seemed upset that nothing happened, especially with a nat 20. We weren't in initiative yet, so every few minutes I was rolling saving throws for the Hag to break out of Hold Person, which she eventually did. Then combat began.

My question is, what is the right call in this situation? Would it have been better to have the Hag actually be intimidated? Or should I have told the Sorcerer that the Hag seems like she can't be shaken and foregone the roll altogether?

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  • \$\begingroup\$ Another similar intimidation question and rolling a Nat 20 \$\endgroup\$
    – MivaScott
    Jun 4, 2022 at 16:34
  • \$\begingroup\$ What was the player's final result? If they have a +5 mod or higher on Intimidate, that would mean their final result was a 25 or greater, which could have pushed it into another difficulty class higher. \$\endgroup\$
    – Nacht
    Jun 6, 2022 at 2:08
  • \$\begingroup\$ Not an answer, but maybe expand on what could be intimidating when considering a situation like this. Could the Hag have actually been plausibly intimidated by the risk of losing the body and what that might mean to her ability to achieve her goals? Or was it truly low-stakes expendable to her? \$\endgroup\$ Jun 6, 2022 at 10:30
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    \$\begingroup\$ Intimidation is basically a threat - do X or else we'll do Y. Both the X and the Y are missing from the description. Those are key elements to determine if a roll should have been made let alone how to resolve that roll. \$\endgroup\$
    – vsfDawg
    Jun 6, 2022 at 12:12
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    \$\begingroup\$ "While holding her, the Sorcerer also rolled a 20 on an Intimidation check". Did you ask for this check or did the player just go for it? The Basic Rules state: "The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure.". Good further reading here: rpg.stackexchange.com/questions/167789/… \$\endgroup\$
    – StuperUser
    Jun 7, 2022 at 14:17

11 Answers 11

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Unless there was a relevant house rule, the right call was probably not to roll.

The first and most important thing to note is that a nat 20 has no special meaning on a skill check. If a result is impossible, then the roll doesn't change that.

Based on your description of the events, then it was probably impossible to meaningfully intimidate the hag under the situation as described since the hag was not and could not have been in real danger.

But generally if something is impossible with a nat 20 under the circumstances, the best thing to do is not to roll at all. Rolling works best when it is meaningful and hopefully creates a sense of either tension or excitement. Being told by the GM to roll and then being told the best possible roll changes nothing is frustrating.

Notably, you ask if you should have told the player to forego the roll so this next part probably doesn't apply to you. But I have been with some players that have a habit of rolling whenever the player thinks a roll is appropriate without waiting for the GM to call for a roll. In that case, skipping the roll as a practical matter can be hard. But this is something to be addressed in your session 0 or out of character. Either a GM needs to houserule that a nat 20 and nat 1 always mean something or the players need to expect to occasionally be told that some rolls were unnecessary no matter what the dice say. Failing to adopt one of those two options is likely to create some frustration.

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    \$\begingroup\$ This answer could be improved with a small example of how to narrate the roll being impossible, because it can also be frustrating as a player to be told they're not allowed to roll in a situation that doesn't immediately reveal why. \$\endgroup\$
    – William
    Jun 5, 2022 at 9:13
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    \$\begingroup\$ @William: Indeed, although perhaps not directly. In this particular example, the Hag could smirk at the threat, or roll her eyes: an experienced player would realize this is a sign, and become wary of the situation, as clearly something is going on that they do not quite understand. \$\endgroup\$ Jun 5, 2022 at 12:02
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    \$\begingroup\$ Isn't it somewhat meaningful in itself to find out that an enemy can't be intimidated? And on a low roll you might not have found that out, and tried it again in combat. \$\endgroup\$
    – towr
    Jun 5, 2022 at 16:03
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    \$\begingroup\$ One other thing worth noting is that a successful check doesn't have to directly "win" or "solve" the entire encounter, you could also give it a lesser effect to make it not completely meaningless. While obviously intimidating the hag into submission is impossible, maybe it could make it hesitate for a moment (perhaps it gets a bad initiative roll) or if the tone of your game fits some humour, perhaps the sudden aggression gets the hag slightly confused and still playing the village herbalist they hand over all their pocket chance or a potion recipe in hopes of getting the assailants to leave. \$\endgroup\$
    – Kryomaani
    Jun 5, 2022 at 22:14
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    \$\begingroup\$ Hmm not so bad. The player on getting a 20 is now certain that the Hag cannot be intimidated. \$\endgroup\$
    – Joshua
    Jun 6, 2022 at 3:21
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While Timothy's answer is correct, I'm copying my answer from another similar question as it is also relevant.


Natural 20 has no bearing on Ability Checks

The rules for Natural 20 state:

If the d20 roll for an attack is a 20, the attack hits regardless of any modifiers or the target's AC. This is called a critical hit, which is explained later in this chapter.

This is strictly for attacks. There is no such clause under Ability Checks:

To make an ability check, roll a d20 and add the relevant ability modifier. As with other d20 rolls, apply bonuses and penalties, and compare the total to the DC. If the total equals or exceeds the DC, the ability check is a success — the creature overcomes the challenge at hand. Otherwise, it's a failure, which means the character or monster makes no progress toward the objective or makes progress combined with a setback determined by the DM.

So by the rules, just because the player rolled a 20 does not mean they suddenly get their heart's desire. It just means they did the best they possibly could.

Most DMs house rule that the skill check works on a sliding scale. So based on how much you exceed or are under the required DC guides how well you did. So if you only needed a 15, but totaled 23 on the roll/score you might get more than just a pass/fail.

This is a house rule, but it's a very popular house rule. So it's likely that the player feels jilted because they got the 20 when it really mattered but didn't suddenly become master of their domain.

In this case, the player made a very convincing argument. But the hag was still in no real peril. However, it would not be out of the realm of possibility for them to worry after a number of successful intimidation checks. The first one just made them realize they were dealing with a group of people that have the means to stop her.

Remember, if a Natural 20 succeeded on every ability check, there is a 5% chance you could intimidate the moon.

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    \$\begingroup\$ As the meme goes, the moon is unphased. \$\endgroup\$
    – Mary
    Jun 5, 2022 at 0:14
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    \$\begingroup\$ And if a natural 1 would fail everything you tried, you'd fall down the stairs 5% of the time you ever get in or out of your house. \$\endgroup\$
    – vsz
    Jun 7, 2022 at 19:41
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The player should have waited for the DM to ask for a roll (or not)

Your game seems to have gone down in the wrong order:

  1. Your player rolled
  2. Your player said what they were going to do
  3. You said what happened (or rather didn't happen)

However, the DM is supposed to ask for an ability check when the player plans to do something that has a chance to fail (meaning not something so easy to be guaranteed and not so hard as to be impossible). Before they roll, the player needs to tell you what they're doing so that you can ask for the roll, assuming the situation calls for it. This serves to prevent disappointing rolls like the one in your game.

The correct order would therefore be:

  1. The player says that they are going to threaten the hag
  2. You say that it's not necessary to roll, and describe the hag's reaction

This is the relevant section of the rules:

The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results. — Ability Checks

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    \$\begingroup\$ From the last sentence "or should I have (...) forgone the roll altogehter" it sounds as if the OP asked the player to roll for the check, so while what this answer says is of course correct, I think it may not be relevant to the situation at hand. \$\endgroup\$ Jun 4, 2022 at 19:36
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    \$\begingroup\$ @GroodytheHobgoblin I'm basing my answer off of what was said earlier in the post: "While holding her, the Sorcerer also rolled a 20 on an Intimidation check and told me what she said to intimidate the Hag". Maybe OP did call for the roll but without getting enough information first, though that wouldn't change my answer. \$\endgroup\$
    – Laurel
    Jun 4, 2022 at 19:44
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Only ask for a check if there is a chance of success, a chance of failure, and a consequence of failure

The PHB gives you guidance for this on p. 174:

An ability check tests a character’s or monster’s innate talent and training in an effort to overcome a challenge. The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results.

You only ask for a roll, if the outcome is uncertain, that is, if the roll has both a chance to succeed or fail. If that is not the case, you just can tell your player that what he tries does or does not work, without a roll. This way, you avoid the kind of frustration your player experienced when they did not succeed, even though they managed to roll the maximum possible result on a roll you asked them to make. Why make me roll at all, if I can't win? is a natural reaction for them.

Information value of rolls

Now, it is not quite that simple. That it is impossible for them to intimidate the "herbalist" (i.e. they do not get to roll) can give the players information that something is not quite right or not what it seems, information that the player characters do not have.

In a way, having them roll disguises this, because you effectively only have to disclose it when they roll very high, while they might be none the wiser when they roll badly. A high roll means the characters make a very convincing argument, and when there is no reaction to that, the characters might be able pick up on it, and suspect something is not right.

However, the rules tell you to not do that, and I also think the light is not worth the candle here. Players often tend to miss subtle clues. It does not hurt to let them have a bit of extra information here, they still need to spot it and think about why they did not get to roll at all.

The full rule when to roll

While we are at this, there is another aspect that is not covered by the guidance in the PHB: cases where there is a chance for failure, but failure has no real consequence.

You should not ask for a roll there either -- unless you rule a single failure means that they are not able to do the task at all. The characters can just retry until they get a high enough result, which just wastes everyone's game time and is boring.

Older editions even had a mechanic for this, called "Taking 20", which meant if you have no limit on retries, you can just declare you spend time until you get it as good as you could. See this excellent article, point 2, by the Angry GM (warning: swearing), for more in-depth discussion on this.

P.S. Intimidation might still work here

You are not sharing details of the situation the hag was in and the way the party threatened the herbalist to allow us to determine if there might have been a chance for her to be intimidated. There sure can be other reasons for her to be afraid than the death of her host. She might be concerned that the party will get wise about her and go after her in the end, for example.

You first need to determine if the threats can have any effect to scare her. If not, don't ask for the roll, tell the player that what he says has no effect. If yes, then have the roll.

Lastly, kudos to you for thinking about how to do this right. You'll never get everything right when you DM in the heat of action, and that is OK, nobody does. As long as you are trying to get it right and listen to the feedback from your players, you're on the right track.

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    \$\begingroup\$ I think this answer touches on an interesting way to handle this: if the players had every reason to believe it should be possible to intimidate the herbalist, one could narrate the result of the high roll by noting the fact that by any measure a normal herbalist should have been terrified by the display of force by the sorcerer, but this "herbalist" just looks unphased - or perhaps the hag might fake being scared! \$\endgroup\$ Jun 5, 2022 at 9:49
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People can be intimidated even when not in physical danger

Imagine you're in some reasonably safe setting, like a classroom or workplace. Imagine some great big muscled dude walks up to within two inches of you, and glares down at you, and doesn't say anything, just growls deep in his throat.

You're not in any real danger, because the authorities are right there, and if this dude tries anything he's going to prison, and he knows this and you know that he knows it.

But you're going to be intimidated anyway, because it's intimidating.

In the scenario you describe, the hag might not stay intimidated forever, but she could easily be intimidated enough to answer some questions for the group before the battle.

The GM's first responsibility is to run a fun adventure

It sounds like you understand that denying a player's move -- especially denying a player's move, that they set up with a spell in advance, and then rolled a nat 20 on! -- isn't fun for the player.

So the question you should be asking is not "is this the realistic thing to do here?" but rather "is there something else I could have done, that would have made the player feel satisfied, without compromising the plot?"

In your situation, I would've been delighted that my players had come up with a complex plan to learn more about the plot. I would've given them the answers they wanted.

It sounds like your real problem is your players shortcutting your boss fight

If I'm understanding correctly, the group won this whole boss fight before initiative was rolled. They cast hold person and the boss failed her save. Their next step could've been to make attacks on her with advantage and autocrit.

It sounds like part of your problem is your players were moving to the interrogation without doing the boss fight you had planned. So you spent the conversation thinking "how can I make sure the fight happens?" rather than "how can I reward the players for being clever?"

My advice for boss fight design is to either (1) give the boss some legendary resistance, or (2) give the boss some minions, so that a single save-or-lose spell won't end the battle.

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  • \$\begingroup\$ A person doesn't even have to be bigger or more imposing. Smaller and weaker people can and do bully larger and stronger people. Psychology is irrational. \$\endgroup\$
    – Beau
    Jun 5, 2022 at 10:40
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Mistakes were made

Natural 20's are one roll in every 20, or so. 5% chance. They happen fairly frequently. So why were your players excited about this one?

  • It happened after the Hag's vessel failed a saving throw, leaving the villain confronted by the heroes in a conversational situation (a very common and much loved trope of the genres of fiction D&D games are drawn from)
  • The sorcerer, who is charismatic, was the one who rolled the natural 20 on a charisma based check. In a situation where a charisma based check was entirely thematic and appropriate.

Many newer players also get excited over 'natural twenties' any time they happen for any reason. This isn't a bad thing. Getting excited over a game you're playing is a great sign that you're having fun.

In this scenario, where a lucky roll coincided with a specific situation where it should be relevant and that was already a tense scene, your players got excited because they expected these factors to lead to something interesting occurring. At least, that's what I surmise from information given - perhaps the rest of the party was just tapping on their phones etc and not interested at all and the sorcerer rolls 18 social checks at every mouse the party encounters along the way.

But the situation sounds dramatic. I'd guess players were interested. So that's the first mistake.

Not utilizing player interest. If players are interested in a situation, or its outcome, going 'uh, nothing happens' is a sure way to not only lose that interest but also make them less interested in the game as a whole. Even if you don't know why they are interested, try to make use of that interest in some way. Introduce a character, have something exciting happen, drop some lore, whatever. You have the attention of the group. Use it.

The second thing i'm more sure about, and that's

Refusing a dramatic offer. The sorcerer player gave you a dramatic offer, a narrative offer, a roleplaying offer, whatever you want to call it - they laid a premise, started a scene (via their actions) and then tossed the ball to you to continue it. Your continuation 'she doesn't seem intimidated' is lacking detail and offers no easy recourse to continue the scene. It's like shutting the door in the face of someone - they will, mostly, leave. If someone then climbs in a window that's pretty rare. Sometimes you should refuse player narrative offers - like when you don't have time, they've had too much spotlight, or the rest of the party isn't interested etc. But in this scenario? When the other party is a major villain, the whole party is there, and it's a classic type of scene that people love? Do something with it. Anything. Spit in the sorcerer's face, have the possessed body bite its tongue, whatever, just don't do 'nothing'.

Finally, there's;

Success or failure is binary. 'Either the hag gets 'intimidated' and then she is ??? defeated? something, or the hag doesn't and isn't'. That's the binary thinking. It goes further. 'If the player succeeds on the roll, good things happen, if not, bad things'. That's another binary thinkingism and they often both happen at the same time. Success always good, failure always bad, single state outcomes, dependent on die roll. That's a major mistake. It makes the game much, much more boring than otherwise. You can make lots of mistakes and still run a fun game, but this one sucks so much fun out of the game it is quite infamous.

Succeeding at a task can make the character's life harder. Climbing into a prison window for example, and then through the window... the character is now in a deep prison cell with no way out but a harder check. Hiding from the sounds they heard (that is their friend come to stealthily find them), success causes them to hide.. from their friend. Great.

Failing at a task can make a character's life easier. They want to Deceive the baron into thinking they aren't sympathetic to the orcs? They fail, and the baron, seeing through this sellsword's ruse, tells them that he too would like to negotiate a peace rather than kill off the orcs. Succeeding there would have left them without a powerful ally (who would think they were just more bloodthirsty racists, and not include them in his plans).

In this situation, you have all kinds of options. Success at intimidation could lead to all kinds of outcomes for the party.

  • the Hag calls in a favour and a Young Black Dragon is sent after the party to remove this threat to her wellbeing. She's scared! So she uses up that valuable favour. And now the party has 2 boss fights to contend with instead of 1. (although she might leg it if they turn out to be strong enough to kill a Dragon)

  • the Hag surrenders, claims she has some excuses for what she was doing, but repents and is now willing to help the party in exchange for mercy. Still a fight scene if they say no, but now they could maybe end up with a kooky potionmaker npc Hag they keep having to keep an eye on so she doesn't steal children

  • the Hag leaves the area. She's still a danger, still developing that mushroom plague or whatever, but now the party can't easily find her. She's a problem for later and will turn up somehow - ideally in some interesting way, like the actual big bad has enslaved her and that's where his poison fog doom timebomb thing came from. A 'your choices in the past created this future situation' thing.

  • the Hag gets very worried! She creates a plan to kill the PCs as soon as possible. Basically what you were going to do anyway but instead of cackling about how she is unkillable she looks terrified and yells 'die! die!' a lot and focuses her attacks on the sorcerer.

  • the Hag gets very worried! Instead of dismissing the PCs as impotent fools, she sets up a plan to poison them using children and a special mushrooom and a complex ruse involving stew.

There's lots of places you can go with it that aren't 'uh... you win' or 'nothing happens', and all of them are far more interesting than either of those options.

Finally, outcomes of checks being binary (yes or no) is bad thinking. You want degrees of success for all kinds of reasons, and you want different outcomes possible dependent on circumstances and also to create interest. If every time someone rolls Intimidate the opponent is either cowed and helpful or angry at you and nothing in between it's weird, awkward, and not interesting. If they show a range of reactions from servility to anger to confusion to 'yeah sure I guess, I don't want trouble' to changing their opinion of the character (like, positively) to assuming you're related to some other threatening force in their life (like a criminal organization) and sending the police after you, etc, it is both more interesting and more believable and helps extend the barebones 5e skill system.

Bad reasoning for having the skill automatically fail - This isn't exactly a 'mistake' per se, but your reasoning indicates that your game might lack verisimilitude - aka, making sense. Lack of verisimilitude is one of those major mistakes that tends to torpedo games.

This is due to your reason for having the intimidate check autofail - the Hag not being physically present. I can threaten someone over the phone. That's what is happening. The sorcerer is threatening the hag over the phone. It's still scary. 'I'll come over to your house and kill you' is scary. They don't need to be physically there for it to be scary. That's something that players would generally expect from a world - that threatening to come over to someone's house to kill them is scary. If that's not the case, and you haven't shown them why this person is unfazed by credible death threats, it seems off.

Lacking verisimilitude is brutal for any game, and you should generally go as far as you are able to try to make sure things in your game make sense to basic logic.


The party is going to go places, and as the DM it is your job to build the roads. Those don't have to be roads of success and glory and fame and fortune. They can be roads of bitter failure. But they have to exist. Players doing things should be part of the story -they are protagonists, their actions, choices, and even thoughts, feelings and attitudes - should be important. If players do things and it does not affect the story, you've dropped the ball as a DM.

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  • \$\begingroup\$ This is the correct response. D&D is mostly an improv session, which means you usually want to reply with 'and then' to keep the scene going. Just because the PCs aren't a mortal threat right now doesn't mean they won't be a threat to the hag's plans, or that they won't be a mortal threat 3 hours-2 weeks from now when the PCs might be in the same physical location as the hag. \$\endgroup\$
    – VHS
    Jun 5, 2022 at 19:20
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I'm gonna go with neither.

Would it have been better to have the Hag actually be intimidated?

Or should I have told the Sorcerer that the Hag seems like she can't be shaken and foregone the roll altogether?

These aren't your only two choices.

One thing to keep in mind with skill checks is ultimately the player has to choose which skill to use, and they don't have all the information. You can deny them the use of that skill in the situation if it makes no sense, but that's a bit agency-inhibiting. Just because it's a stupid thing to try and can't possibly succeed doesn't mean a character won't try it. Some of the most interesting and hilarious moments in stories come from exactly that.

So my advice is: don't be too quick to deny a skill check, but try to have a few tidbits of information in your encounter design that the players don't know that you can use to pay off wildly successful stupid actions, or punish wildly unsuccessful ones.

I had a similar case just a few weeks ago. An army was attacking the keep that my heroes use as a base. The attack started with an invisible giant suddenly appearing and blocking the drawbridge and portcullis from being closed.

One of the players tried to Persuade him to surrender, and rolled a nat 20. Now, this giant was never going to simply be persuaded to give up, but trying this was consistent with the character's backstory/class (Oath of Redemption Paladin) so I wanted to reward the good roll and the good role-playing. Just because actual persuasion couldn't be the outcome doesn't mean I couldn't reward the character for interesting play and a good roll. So the giant engaged with him briefly, laughing at him and berating him for being cowardly and trying to talk his way out of a beating. But in that exchange he gave up some critical info about the rest of the threat; how soon the enemy would be here and some general info on their forces.

Similarly, Intimidation may be meaningless to a hag inhabiting someone else's body, but a particularly strong intimidation attempt, and its' obvious failure, might make the hag overconfident and cause her to say something useful. Not because she was intimidated, but because the player was interacting in the best way they could think of, and they rolled amazingly well.

I can't actually intimidate the moon, but what's the better story?:

  1. Nothing happens, or
  2. Your audacity catches the ear of the moon goddess, who sends an avatar down to see what all the fuss is about.
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Casting Hold Person should have triggered initiative

You write:

We weren't in initiative yet, so every few minutes I was rolling saving throws for the Hag to break out of Hold Person, which she eventually did. Then combat began.

First, Hold Person has a duration of only one minute. So at most you should have waited for one minute before the Hag got out of Hold Person.

Second, and maybe more importantly, casting Hold Person is a hostile action, and trying to do so should trigger initiative. There are in depth discussions about when exactly combat begins, and what counts as surprise when one side without warning takes hostile action. But even surprise is just a preliminary step before rolling initiative and entering round-based combat. See the rules under Combat Step by Step (PHB, p. 189):

  1. Determine surprise. (...)
  2. Establish positions. (...)
  3. Roll initiative. (...)

It may be that you rule the hag was surprised by the casting, and did not get to act on her own turn, but she still would be in initative order then and get to re-save every round.

See my other answer for how then resolve the intimidation roll, which could happen on the following round.

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Roleplaying solution:

The hag is impersonating someone. She might well have pretended to be intimidated (while divulging only irrelevant information).

The roll would be there to fool the player, who without a roll would wonder what's going on. If you let him roll, understand as the GM that the hag is not intimidated but can judge if she thinks the intimidation attempt is pathetic or would work on the person she's impersonating, and then act accordingly.

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There's already some great answers here, but I wanted to add a bit more advice.

Hold Person won't affect a hag. Hold Person only affects

a humanoid that you can see within range

but while you didn't say what kind of hag it was, with the exception of one humanoid hag in Tomb of Annihilation, hags are generally Fey, or for Night Hags, Fiends, thus would not be affected by Hold Person.

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Ask the player to roleplay their intimdation before asking for a roll

A lot of answers are saying something along the lines of "if the hag can't be intimidated then you don't roll" and this is true, but maybe the player has something up their sleeve that you haven't considered. Perhaps the player wasn't going to physically threaten the hag but take some other approach you hadn't thought of. Just because you can't see how to do it doesn't mean the player can't see a way. As DMs we often over look other solutions, thats how our players keep us on our toes.

If the player goes the route of physical threats then you can tell them not to bother rolling and have the hag give their reasons for not caring (or they figure it out once the hag leaves the body, then you can debreif the players on why the hag couldn't be intimidated by violence).

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