D&D 5E When To Roll Persuasion?

[Greenstone.Walker]

EDIT: I'll add that I realize this won't sit right with some people. Some of you probably think that a great plan, or great acting, or whatever, should somehow alter the odds of success. I also have played that way a lot, and sometimes still do, but overall I think I prefer to be the neutral arbiter, not the evaluator of how good somebody's plan/acting is.

I'm with Elfcrusher on this. It doesn't matter how persuasive the player is; if the character has low CHA then the character is not good at persuasion.

I've seen this abused three or four times. Highly persuasive people taking low CHA-type attributes but still trying social tasks, relying on their acting to sway the game. It usually succeeded, but when it didn't succeed, it ended in a tantrum.

I think the player skill vs character skill balance is tricky, because we do want our players to have some skills, particularly in the combat pillar.