A group of bandits travels through the forest towards their campsite. The rustling of leaves overhead as if a soft breeze was blowing. The rear-guard disappears, yet none of his fellows notice. The next in line falls soon after, his body disappearing into the foliage surrounding the trail. More soon follow, and the leader begins to panic as his men are disappearing from the trail, seemingly abandoning him. As the driver next to him is pulled up into the trees above, he flees through the forest. A rustling of leaves to his right catches his attention, and as he looks towards it, something rushes in from his left and he falls limp, a blade planted in his throat.

The Whisperleaf Interceptor is a highly trained tracker and hunter. Taken from their home in early childhood, the Whisperleaf Company trains them in the arts of stealth, assassination, non-lethal takedowns, and tracking. When a Whisperleaf Interceptor is hunting you, there is little hope of escape.

Whisperleaf Training

Your assignments take you through the wilds quite often, and as such you need to know how to survive and still implement your skillset. You have been trained to spot natural obstacles, hiding places, poisonous plants, and how to track a creature.

Gain proficiency in Nature and Survival.

If you already have Proficiency in one or both of these skills, you instead gain Twice Proficiency in the skill.

Designer Note: I could not figure out how to make the subclass auto-detect for proficiency and to apply Twice Proficiency and apply that instead. The easiest workaround to this is to add a custom item giving twice proficiency in the skills, provided you had proficiency in the first place.

Whisperleaf Combatant

The Whisperleaf Interceptor is trained in a unique blend of crossbow and blade utilization. Trained to be able to throw or strike with a blade and follow up with a crossbow bolt, or shoot first and stab second.

This blend of different attacks catches many foes off-guard. You get the Crossbow Expert feat for free, but it only applies to the Hand Crossbow. If you already have this feat, choose another instead. In addition to the normal effect of the feat, you can use the weapons in reverse as stated below.

• When you use the Attack action and attack with a hand crossbow, you can use a bonus action to attack with a one-handed weapon you are holding.

Lastly,  If you did not apply Sneak Attack this turn and struck a creature with attacks from two different weapons, you may apply Sneak Attack damage to the second attack, as your very erratic style will catch most foes off guard.

Falling Leaf Technique

Years of training in the canopies of forests, on rooftops, and on the support beams of ceilings has taught you how to make the most of falling or jumping from high up. 

If you would suffer fall damage, you may use your reaction to reduce the damage you would take by 5 times your rogue level. You always end up on your feet at the end of a fall.

Additionally, on your turn you may use the Falling Leaf Technique described below.

You may use part of your movement to voluntarily fall. Any distance fallen does not count towards your movement for the turn.

• During your fall, you may take the Attack Action.
• If successful, calculate the total distance you will have fallen, and halve the result. Add this number to your total damage dealt.
• If successful, you may apply Sneak Attack if you have not done so this turn.
• Lose your reaction for the turn.
• Reduce the fall damage you would take by 5 times your rogue level.

You choose an adjacent square to the creature struck to land in. Movement made after the fall does not provoke attacks of opportunity.

Example: A 10th level rogue jumps from the top of a 50 foot tall building (using 5 feet of movement to do so). During the fall, he makes a single dagger attack roll. He is successful, and rolls his damage, choosing to add sneak attack. He adds 25 to the final result of the damage (50 divided by 2). He loses his reaction, and takes 0 damage (10 rogue levels x 5 - 50 feet of fall damage negation), and uses the remaining 25 feet of movement to run from the scene.

Interceptor's Prey

Once per Long Rest you may designate a creature you can see as your Prey as a Bonus Action. The creature is marked as your Prey until you use this ability again, they die, or you dismiss the mark as a Free Action.

• The creature has disadvantage when attempting to notice you (Perception, Investigation), tracking you (Survival), or seeing through a ruse (Insight).
• The creature treats their Passive Perception and Passive Insight as 10 lower in regard to your presence or activities.
• You gain Advantage on Survival skill rolls to track your Prey.
• You automatically deal a critical strike on your first successful attack roll against the creature.

If you would reduce the creature to 0 hit points while they are marked as your Prey, you may instead leave them alive, but unconscious for a number of minutes equal to your Rogue level. Magical Healing will not wake them up but may bring them to a positive hit point total. You may wake them from unconsciousness whenever you wish.

Whisperwind Bladestorm

Once per long rest, you may take the special Attack Action known as the Whisperwind Bladestorm.

Using an Attack Action, designate a creature you can see through any means. If there is air around the creature, they can be subject to the Bladestorm. If there is no air present, the attack does not work and the ability use is refunded.

You assault the target with a hail of blades formed from the air around them. Make an attack roll with Advantage using your Dexterity modifier and Proficiency Bonus. If you succeed, you deal 1d6 points of slashing damage per Rogue level you have as a single instance of damage. This damage is physical in nature, but counts as magical for the purpose of overcoming resistance. 

You may apply Sneak Attack to this ability.

You cannot use this ability with the automatic critical feature from Interceptor's Prey. The automatic critical feature remains active on your Prey, even if this ability is your first attack against the creature.