Brigand

Brigands practice larceny and combat on the highways, holding up travelers, merchants, and caravans at swordpoint and gunpoint. Often labeled as bandits and highway robbers, a brigand (as far as rogues go) is a cut above the average robber. Though stealth is an important factor of their jobs, brigands prefer a more aggressive approach, using ambushes to gain the upper hand and guerilla tactics to maintain it. Though bandits also practice these strategies, brigands perfect them.

Ambusher

Beginning at 3rd level, you can perform ambushes with greater success. After exploring an area up to 50 feet on any side for 10 minutes or more, you have advantage on Dexterity (Stealth) checks made to hide in that area. During those 10 minutes, you are planning out how to best hide yourself from potential targets or dangers. If you leave the area, you can maintain this benefit for 1 hour afterwards.

Guerilla Tactics

Also starting at 3rd level, you excel at fighting harried enemies, whether they are under assault or being threatened by a nearby foe. You can apply Sneak Attack damage to a creature that has taken damage from a weapon or spell attack since the end of your previous turn.
    Additionally, you have advantage on melee weapon attacks against a creature if another hostile creature is within 5 feet of your target.

Hit and Run

Also beginning at 3rd level, you are adept at stealing objects quickly under pressure. As a bonus action, you can use your thieves’ tools or an object to attempt to open or break a lock. You can also use your bonus action to pick up and stow an object.

Size Up

By 9th level, you have learned how to spot high-value targets and goods. While observing or inspecting cargo or humanoids for 10 minutes, you can learn the following information. To successfully observe a humanoid, you must succeed on a Wisdom (Insight) check contested against their passive Deception score (10 + the humanoid’s Deception skill bonus). Successfully observing a humanoid allows you to learn about any armor, weapons, or items the humanoid has equipped, but not about any of their belongings hidden in pockets or other containers.

Cargo
- The type of goods carried in select cargo,
- The approximate value of the goods, and
- How well-protected the cargo is (e.g. types of locks, packaging material, weight, etc.)

People
- How wealthy the person is, and
- What type of equipment the person has on them

Slip Through

At 13th level, you have learned how to aim your attacks through openings in an enemy’s armor, as long as you remain close to them. Whenever you attack an enemy wearing light, medium, or heavy armor, you treat the attack as if hitting its unarmored AC (10 + Dexterity modifier + proficiency bonus, unless indicated otherwise) or its natural armor, as long as you meet the following conditions:
- You are within 5 feet of the creature,
- You are attacking with a finesse weapon, and
- The enemy’s hit points are lower than its hit point maximum.

No Mercy

When you reach 17th level, you can brutalize an enemy to finish them quickly. If you take the attack Action on your turn to make a melee weapon attack against a creature, you can make an additional melee weapon attack against the creature. The additional attack can benefit from your Sneak Attack, even if you have already used it this turn; however, you cannot add your proficiency bonus to this additional attack.