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Message: <blockquote data-quote="merwins" data-source="post: 7054346" data-attributes="member: 6829883">So, just to close the loop, here's how I resolved the situation: The familiar can do exactly what the orc did. Rush in, and attempt to find the opponent using sound, movement and their intuition as to where the "center" of the darkness is. The part that stuck in my craw was that the familiar could potentially help the Trickster with no consequence to the Warlock. Both the Orc and the Warlock are equally difficult targets, and potentially in very close proximity. And I don't think 5E has rules for firing blindly into melee -- If you miss target X, what about target Y? So I gave the Trickster player a choice. They could take the standard disadvantage for firing into darkness OR they could negate the disadvantage with their familiar. BUT, if they negated the disadvantage (increasing their chance of hitting the Orc) and they failed, they'd have to make a second attack roll for friendly fire against the Warlock, reflecting the greater likelihood that their arrow would find any target. Just one of many possible solutions, but my players were content with it.</blockquote>