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It's clear that we should roll Insight versus Deception (I guess) , but what should be rolled against Persuasion or Intimidation checks? Is the answer to this question different for NPCs and PCs?

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The DMG says:

Some DMs prefer to run a social interaction as a free-form roleplaying exercise, where dice rarely come into play. Other DMs prefer to resolve the outcome of an interaction by having characters make Charisma checks. Either approach works, and most games fall somewhere in between, balancing player skill (roleplaying and persuading) with character skill (reflected by ability checks).

So don't feel you need to involve a roll at all. You can handle this with pure roleplaying.

It goes on to outline a suggested system whereby you use the situation and the PCs' initial interaction to determine if they are friendly, indifferent, or hostile followed by a Charisma check where DC 0, 10, and 20 give different results depending on that attitude.

e.g. A friendly NPC will help, providing there is no risk or sacrifice on a 0 and will take a significant risk or sacrifice on a 20. A hostile NPC, on the other hand, will only help if there is no risk/sacrifice on a 20 … and will actively oppose the PCs on a 0.

Note that since it is a flat DC, the NPC doesn't roll anything.

Is the answer to this question different for NPCs and PCs?

Most players find having their agency taken away to be not fun. Forcing them to have specific behaviour or take specific actions with rules (be it through Charisma checks or spells like Charm Person or Dominate) is best avoided. Roleplay the persuasion instead.

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  • 2
    \$\begingroup\$ This is the answer I would give. I would add that while "always roleplay" is a perfectly fine solution to maintain player agency, it's not the only one - in fact there is one which is in line with the rest of your answer. Specifically letting the PC target of the persuasion attempt copy the DM loop: (1) PC decides whether they could ever be swayed about this (2) PC (explicitly or just in their head, I prefer the latter) sets one or more DCs for the check, defining what hitting each would mean (3) persuading PC makes the roll (4) target PC reacts. \$\endgroup\$ – Vigil Jul 15 at 9:11
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Nothing, probably

5e diverges from the "I use X skill" mentality. You describe what do you do, then the DM might ask you for an ability check, then the DM describes what happens.

Making arguments under pressure is usually a Charisma check, with or without proficiency bonus (DM's choice), as Charisma is "measuring force of personality" according to the PHB.

However, if one PC is trying to persuade the other one, DM is not involved at all! Instead of saying "I'm trying to persade Fred not to do this" to the DM, you might say "Fred, I don't think it is a good idea" to the Fred's player himself. You don't need to roll anything in this case, neither does Fred (unless your DM says otherwise), moreover, it is a perfect opportunity for some roleplaying.

An addition from comments (@aherocalledFrog): Some players could see their character going either way when being persuaded by another player, and can choose to leave it to chance. If they do decide to roll something to see if their character is persuaded, they can ask the DM for recommendations, but it's up to them.

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  • \$\begingroup\$ Some players could see their character going either way when being persuaded by another player, and can choose to leave it to chance. If they do decide to roll something to see if their character is persuaded, they can ask the DM for recommendations, but it's up to them. \$\endgroup\$ – aherocalledFrog Jul 16 at 2:15
  • \$\begingroup\$ @aherocalledFrog fair point \$\endgroup\$ – enkryptor Jul 16 at 8:55
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Insight is a perfectly fine skill to use in this situation...if you feel the situation warrants an opposed roll

Not all social interactions require ability checks, nor do they all require opposed rolls.

The DMG has a good section on how to run social interactions without requiring opposed rolls which is worth a read. It also includes this advice (emphasis mine):

Some DMs prefer to run a social interaction as a free-form roleplaying exercise, where dice rarely come into play. Other DMs prefer to resolve the outcome of an interaction by having characters make Charisma checks. Either approach works, and most games fall somewhere in between, balancing player skill (roleplaying and persuading) with character skill (reflected by ability checks).

If you feel and opposed roll is warranted in the situation, then Insight is a fine choice.

The PHB defines Insight as

Your Wisdom (Insight) check decides whether you can determine the true intentions of a creature, such as when searching out a lie or predicting someone’s next move. Doing so involves gleaning clues from body language, speech habits, and changes in mannerisms.

If someone is trying to persuade a PC or an NPC to act a particular way, being able to discern the true intentions of the creature should certainly inform how persuadable the person doing the persuading is.

Alternatively a general Intelligence check,

An Intelligence check comes into play when you need to draw on logic, education, memory, or deductive reasoning.

or a general Charisma check (emphasis mine):

A Charisma check might arise when you try to influence or entertain others, when you try to make an impression or tell a convincing lie, or when you are navigating a tricky social situation.

might also be appropriate to call for given the situation.

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