I will allow a character Trained in a Skill or Tool to automatically succeed on a Skill check. This mostly depends on the situation the character is in, usually there is no direct threat or there is an important clue I want the player to find.
As an optional rule, if two characters are trained in a Skill that would help in their current situation, even if there is a looming threat (but not in combat), if they work together, they will automatically succeed, as well.
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