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Message: <blockquote data-quote="merwins" data-source="post: 7052571" data-attributes="member: 6829883">How would you rule this, or want it to be ruled? Enemy: Orc that's smarter and stronger than the average orc. Player character: Warlock who has cast Darkness on a mobile source that she's carrying. She also has Devil's Sight. Player character: Arcane Trickster with a FamiliarOrc outside the Darkness assesses the situation and figures out that the Warlock is likely in the center of the Darkness. Rushes in to attack. His initiative is after the Darkness is cast, but before the Trickster acts.  Trickster on the outside of the Darkness sends his Familiar in to Help him attack. Easy decisions: Warlock has advantage on all targets. Trickster has disadvantage on all targets. Familiar can't attack. More difficult decisions: Determining where combatants are inside the Darkness. Determining whether the Familiar is allowed to Help when it can't see. Determining if the Trickster can be helped when he can't see anything in the Darkness. RAW: Help for attacks doesn't require sight, just the 5 ft proximity. Would you allow the Trickster to negate his disadvantage on attacking the Orc within the Darkness? Why or why not? And what happens if the Trickster misses his shot? No consequence/risk for the Warlock in the Darkness? What would you rule? I'll post my compromise solution tomorrow. As with all compromises, no one was unhappy or happy, but we got past the rough edges on the encounter. There's going to be a LOT more of this. I expect my players to get creative with their abilities.</blockquote>

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