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Message: <blockquote data-quote="Benjamin Olson" data-source="post: 7868790" data-attributes="member: 6988941">1. If more than one skill and/or tool is relevant I would either do two rolls with the success of one granting advantage, a lower DC on the other, or both, or else just say that just having proficiency in the one thing allows them to roll for the other with advantage, a lower DC etc, or perhaps just allows them to roll at all when it is something like proficiency in a musical instrument for a performance where, if they are not proficient, there is no way they could use it effectively (my guess is that this is how most musical performances are handled). Advantage is best (when +4ish seems appropriate) because then the player knows what they got out of the first success, unless I am actually telling them the DCs, which I rarely do, but if it is some sort of crafting thing they will do repeatedly I would.2. Players generally don't get to keep rolling on an ability check until someone succeeds. Where appropriate, one can take the help action to give another rolling on behalf of the group advantage. That said, if one person wants to attempt the same thing using a different skill or a different tactic with the same skill that's usually fine, and might make a lot of character sense. Also letting two people attempt separately is not as advantageous for them as just granting advantage to the one with the highest modifier, but it often makes sense character wise and makes play less of a bummer for the player who invested in a skill but still has a lower modifier than someone else in the group. Still, once you get past the second person they've got to have a creative new angle on the thing.3. It is almost always easier to deceive effectively by telling the truth in a misleading way than by lying outright, but fundamentally they are still being deceptive. Generally they should just get a lower DC or advantage on the deception check if it seems like this use of truth would make their deception more effective. However, in some circumstances misleading use of truth may fall more in the persuasion or even performance categories. Also you can just decide that for the purposes of this roll they are proficient in deception, if that is the issue. If, in an extreme example, they conceal their identity by giving X name they no longer go by from the life they left behind as a dirt farmer or whatever, they are presumably nevertheless hyper-proficient in saying "my name is X", and have proficiency with this deception even if they normally don't have proficiency in deception.</blockquote>

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