Bandit

You survived by taking from others -- robbing travelers on lonely roads, ambushing merchant caravans, or demanding "tolls" from those passing through your territory. Perhaps you were a desperate soul with no other options, a member of an organized gang, or even a sanctioned outlaw working under the protection of a corrupt noble. Whatever the circumstances, you learned how to identify easy marks, set up ambushes, divide spoils, and disappear before the authorities arrived. Now you've moved on to adventuring, but old habits die hard.

Ability Score Adjustments: +1 Dexterity or Charisma, +1 on any other ability

Skill Proficiencies: Intimidation, Stealth

Tool Proficiencies: Thieves' Tools

Languages: None

Equipment: A dark cloak with a hood, a face covering (mask or scarf), a set of common clothes, a signal whistle, 50 feet of hempen rope, and a belt pouch containing 10 gp

Feature: Ambush Expertise

Once per long rest, when you are in terrain with natural cover (forest, hills, ruins, etc.), you may ambush one creature that has not yet taken an action in the current combat. You gain advantage on your first attack roll against this creature. You also add a bonus of 1d4 points to your damage roll on this attack.