Highwayman

"The road is mine, and so is your purse. Stand and deliver!"

Highwaymen are daring rogues who live by speed, steel, and spectacle. They are the masked legends of the open road—part thief, part folk hero—known for their ambushes, dramatic escapes, and the fear they strike into the hearts of the wealthy and corrupt. Whether slipping through city alleys or vanishing into the woods, a Highwayman is always one step ahead of the law and two steps ahead of their mark.

Highwayman Subclass Features
Level	Class Feature
3	Intimidating Scoundrel, Flintlock Training, Mounted Rogue
9	Terrifying Bandit, Mounted Imperiousness
13	Smoke and Flash Powder
17	Legend of the Road, Master of Fear

Level 3: Flintlock Training

At 3rd level, you gain proficiency with flintlock pistols and other black powder weaponry. Whenever you make an attack with a flintlock pistol, you may treat it as a finesse weapon for the purpose of Sneak Attack.

Level 3: Mounted Rogue

At third level you have an uncanny bond with your trusty steed. You can cast Find Steed once per long rest without expending a spell slot.

At third level your mastery of mounted combat allows you to move swiftly and strike fear into your foes. While mounted, you gain the following benefits:

• Advantage on Dexterity (Acrobatics) checks to stay mounted in precarious situations.
• You may use Charisma instead of Strength when making checks to control mounts.

Intimidating Scoundrel

You gain proficiency in Intimidation, and if you already have proficiency, this ability grants you expertise.

Level 9: Terrifying Bandit

As an action, choose one creature within 30 feet that can see and hear you. That creature must make a Charisma saving throw (DC = 8 + your Dexterity modifier + your proficiency bonus).

• On a failed save, the creature is frightened until the end of your next turn or until it takes damage—whichever comes first.
• You can use this feature a number of times equal to your proficiency bonus, regaining all expended uses after a long rest.

Mounted Imperiousness

While mounted, you have advantage on Intimidation checks.

Smoke and Flash Powder

As a bonus action, you can throw a specially prepared flash powder bomb at your feet.

• Smoke Cloud: A 20-foot-radius sphere centered on you becomes heavily obscured with thick smoke for 1 minute.
• Blinding Flash: All creatures within 30 feet who can see the flash must make a Constitution saving throw (DC = 8 + your Dexterity modifier + your proficiency bonus).
• On a failed save, the creature is blinded for 1 minute. It can repeat the save at the end of each of its turns.

Immediately after using this feature, you may take the Dash or Disengage action as part of the same bonus action.
You can use this feature a number of times equal to your proficiency bonus, regaining all expended uses after a long rest.

Level 17: Legend of the Road

When you roll initiative, you may immediately make a Charisma (Intimidation) check contested by the Wisdom (Insight) of each creature of your choice within 60 feet that can see or hear you.

• On a success, the creature is frightened of you for 1 minute.
• While frightened in this way, the creature has disadvantage on attack rolls and ability checks while it can see you.
• A frightened creature can repeat the saving throw at the end of each of its turns, ending the effect on a success.

You can use this feature once per long rest.

Level 17: Master of Fear

You gain the following benefits while interacting with frightened creatures:

• Advantage on attack rolls against frightened creatures.

When you deal Sneak Attack damage to a frightened creature, you can reroll any 1s or 2s on the damage dice.