As a bugbear, does your target have to have the "Surprised" condition in order for your Sneak Attack trait to trigger? @JeremyECrawford

— baby eatin, satan lover (@fartboss) August 3, 2018

The bugbear racial trait Surprise Attack does require the target to be surprised. That's what it means when it says, "If you surprise a creature …" #DnD https://t.co/YH8gKLAEWo

— Jeremy Crawford (@JeremyECrawford) August 3, 2018