Base Class: Rogue
Attacks from their scimitars or horsebows can catch enemies unaware or leave them off balance for allies to follow up with heavier strikes. Most armies and caravans will attempt to hire Outriders to ensure their way is clear if they can afford the price. Criminal organizations use them to make covert deliveries and keep lookout when necessary.
Light Cavalry
Starting at 3rd level, you gain proficiency with scimitars and Animal Handling, and you can add double your proficiency bonus to any ability check you make in Animal Handling. If you are not wearing medium or heavy armor and are mounted on a creature that is not wearing medium or heavy barding, your mount can use your Stealth modifier for any Dexterity (Stealth) check it makes, and when you use your Cunning Action to Disengage, your mount gains the benefit of the Disengage action as well.
Harrying Strike
Also at 3rd level, you are skilled at striking multiple enemies quickly. When you deal Sneak Attack damage to a creature on your turn, you can immediately move up to half your speed without provoking opportunity attacks and make a weapon attack against another creature. If you are mounted, your mount can move half its speed instead, and neither you nor your mount provoke opportunity attacks.
On a hit, the creature takes the weapon's damage and half the number of Sneak Attack dice for your level (round up). You can use this ability a number of times equal to your proficiency bonus and regain all uses when you finish a long rest. When you reach 9th level in this class, if you roll initiative and have no uses of this ability remaining, you regain one use.
Forerunner
By 9th level, you are as light on your feet as you are in the saddle. Your movement speed increases by 10 feet. If you are mounted, your mount's movement speed increases by 10 feet if you are not wearing medium or heavy armor and the mount is not wearing medium or heavy barding.
Stunt Riding
Also at 9th level, any mount you are riding gains the benefit of your Evasion feature, and if your mount is hit by an attack, you can use your reaction to half the damage it takes.
Beleaguer
By 13th level, you can create openings in enemies for your enemies for allies to exploit. When you use your Harrying Strike, the creature you dealt your Sneak Attack damage to is left open to attack. The next time a creature other than you makes an attack against it before the start of your next turn, they have advantage on the attack roll. If the additional attack you made as part of the Harrying Strike hit, the target suffers the same vulnerability.
Overrun
At 17th level, you are a master of keeping your enemies off balance. When you use your Harrying Strike, the creature you dealt your Sneak Attack damage to takes an additional 3d6 damage and must make a Strength saving throw (DC = 8 + your Dexterity modifier + your proficiency bonus) if it is Large or smaller. On a failure, it is knocked prone. If you are mounted and dealt the Sneak Attack with a melee attack, they have disadvantage on the saving throw.
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