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Message: <blockquote data-quote="Esker" data-source="post: 7936746" data-attributes="member: 6966824">Gloomstalker and Assassin pair really well together: the extra initiative boost helps you get that first round advantage, and then you also get an extra attack during that round when you have it. Plus, being invisible in darkness vs creatures who rely on darkvision means I'd pick up your ASI at 4th first, but then taking your next three levels in ranger for Gloomstalker is not a bad idea at all, IMO (and once you're to ranger 3 you may as well go to ranger 5 for extra attack).You do miss out on 2d6 sneak attack dice, so for levels 5 and 6 you'll be slightly behind where you'd be as a straight assassin, but at Ranger 2 you do get that fighting style; the extra +2 to hit from archery style is certainly welcome on a rogue, even if it's diminished slightly when you already have advantage. You can also get Hunter's Mark, which helps close the sneak attack gap.At ranger 5 you can pick up Pass Without Trace, which would really help your party get surprise. Healing Spirit is another great 2nd level ranger spell.</blockquote>