Surprise Attack within Party

[deljzc]

That's not the only circumstance in which a creature can be surprised. If you're in a peaceful situation with non-hostiles, then one of them drawing a blade and attacking while the others are in conversation can also count as a surprise attack.

What you could also do, is have the level of the Rogue be equal to that of the players. Don't make it a combat opportunity by giving the Rogue a guaranteed means of escape (either extra movement, or jumping onto a riding cart, or whatever). Instead, make his attack a poisonous one - one that isn't easily healed. Then you also have a nice plot hook where the party has to find a way to cure their party member.

I agree. I'm going to have to redesign the original NPC a bit to balance things out. Just making it a level 2 rogue does wonders. That's only 1d4 + dex damage. Any way you see to get advantage anywhere? He could attack during an encounter, then his "within 5' of an enemy kicks in" maybe. Adding poison might be difficult since his weapon is "borrowed" from the characters. If anything, I could run a "chase" scene using some of the alternate rules out there on the web. Those can be fun.

I have to say, there's a big difference in this scenario between a 2nd level rogue and a 3rd level rogue/assassin. Maybe too much.