Cap'n Kobold
Hero
The character may well believe that the sword is worth what the NPC is asking for it, but they are free to decide that they just don't want an extra-expensive sword, and ask the NPC if they have anything cheaper.Scenario: NPC sells weapons. He claims that his greatsword is of special quality (but the DM knows the guy is a liar), and wants to sell it to the PC at 5x the listed price in the PHB, even though in reality it's just an ordinary greatsword.
The PCs are interested to buy a greatsword, especially if it has special properties (and let's assume they cannot check it for magic properties and aren't proficient in smith's tools).
Now the NPC makes a deception check and rolls a natural 20, for a total of 27. Does that mean that the PC must now buy the sword at 5x the market price, even if the player behind the PC suspects that he's being deceived? I would consider that player "forced" to buy that sword.
I think that the player should have freedom to refuse that sword at all times, no matter what the DM rolls. It's up to the DM to put up some decent roleplay. And in addition, the player can attempt to see through the lies with an Insight check.
Generally no. Because I have both the Characters' passive Perception and Insight available to be, even if I ask for a roll, the player may not know what it was for.Have you ever noticed any meta-game gotchas? Such as the PC knowing they just rolled Insight and experiencing a degree of internal dilemma? That might not be a strong, subversive or bad faith dilemma.
It might be something like - I may have been going to lean into not trusting this NPC, but now that I have rolled Insight it's hard for me to do that with a completely clear conscience, so I guess I better just trust them.
If I'm expecting to need that sort of thing, I have asked the players to make some D20 rolls before the session begins, and I will apply them to whatever checks needed.
However, most of my players are pretty good roleplayers and so that sort of precaution is generally unnecessary.