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Message: <blockquote data-quote="CapnZapp" data-source="post: 7366897" data-attributes="member: 12731">I'm the DM and I'm having quite the conundrum. My Rogue player is hopelessly behind in damage (the rogue class really is impossible to min-max the way the others min-max other classes), and even though I'm the DM I'm having trouble finding was to help.My goal is specifically to open up the window of a second helping of sneak damage.This is because I believe that would gel with my player's preferred playing style, which is very straight-forward. The entire business of optimizing opportunity attacks does not seem to engage him, and as far as I'm aware that's the only legit way of getting a shot at a second sneak.Yet, he's clearly disappointed everyone else outdamages him.We're playing a game with items, feats and multi-classing; and the rogue simply doesn't keep up.So now I wonder, what canon or even semi-canon ways are available to me to introduce a magic item that helps with this situation, drawing from both 5e and 3e magic items.Let me give you an example: the dancing weapon. In 3e it wasn't a stretch to allow this to make a sneak attack. But in 5e; not only is it outruled by RAW, the dancing attack happens on the Rogue's turn, so it really is a non-starter. Any other item or effect I could use?Ideally, I'm looking for another way to make an out-of-turn attack other than the opportunity attack (since this seems to be a difficult or underhanded concept).But in a pinch a magic effect that triggers an OA would do, since that opens up the possibility of a second helping of sneak damage, which would do wonders helping this character stand his ground against the rest.The Rogue really is frustratingly underpowered for such a squishy chassi; there are no feats, no class abilities and no DMG items that increase sneak damage! [emoji20](We jointly decided against the Assassin subclass - it simply will not enter play often enough to be justified)Anyway, any suggestions, any old d20 systems mastery, would be appreciated ☺</blockquote>

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