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Recently started DMing and, during the game, they captured a Goblin and attempted to pry information from him.

My question is, is every player allowed to roll intimidation/persuasion in an attempt to individually coerce the Goblin? On that note, if a PC fails their intimidation can they also roll persuasion after (although if I allow it I'd do so with disadvantage as they just attempted to coerce the creature in the polar opposite way).

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    \$\begingroup\$ You might want to look at this question or this question. \$\endgroup\$
    – Miniman
    Nov 4, 2015 at 22:17

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From the rules:

Working Together

Sometimes two or more characters team up to attempt a task. The character who’s leading the effort—or the one with the highest ability modifier—can make an ability check with advantage, reflecting the help provided by the other characters. In combat, this requires the Help action (see chapter 9). A character can only provide help if the task is one that he or she could attempt alone. For example, trying to open a lock requires proficiency with thieves’ tools, so a character who lacks that proficiency can’t help another character in that task. Moreover, a character can help only when two or more individuals working together would actually be productive. Some tasks, such as threading a needle, are no easier with help. (PHB5e p.175)

This means the character who is interrogating the goblin with the highest charisma modifier gets to make a check with advantage. No one else makes a check.

If the players switch up their tactics, then a new check is performed. It's up to you, as a DM, to determine when a new check can be performed.

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    \$\begingroup\$ I'd stress that it's up to you (DM) to determine if and when any check if performed--not just a re-check. The interrogator makes a check if the GM asks for one. "Working Together" doesn't supersede the general notion that GMs always are the one to ask for a check, not players. (Though we players might gently suggest that our situation might warrant a check.) \$\endgroup\$
    – nitsua60
    Nov 4, 2015 at 23:27
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    \$\begingroup\$ Players should be rewarded for ingenuity. If they can come up with a plausible cause (they took some effort to justify it), I'd be more inclined to include the effects of the rule. They might claim to be playing good-cop/bad-cop, or perhaps some special technique, or ... whatever. Going out of the way to encourage player teamwork fosters more teamwork, which is the main attraction of the game. \$\endgroup\$
    – phyrfox
    Nov 5, 2015 at 7:13

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