Skulker

Haunter of dimly lit passageways, shaded undergrowth and obliviously crowded streets, the skulker is well-accustomed to marking, trailing and incapacitating solitary prey. Whether they hunt for professional or more nefarious means, they carry out their operations with careful, calculating patience, and a total lack of sympathy for their quarry. When a skulker sets their crooked gaze upon a target, the creature is unaware that with every step they take, they are a silvered flash away from never being seen again.

Fade into the Crowd

Starting at 3rd level, you become adept at concealing yourself among the oblivious masses. You have advantage on Dexterity (Stealth) checks when attempting to hide behind or among multiple people. (This bonus does not apply if the people you are hiding among are also trying to hide.)

Stalker's Snare

When you choose this archetype at 3rd level, your surprise attacks become tailored to prevent escape. After a successful Sneak Attack, you may roll a D6 to determine a snare effect, choosing beforehand to add or subtract 1 from the roll's result. You may use this ability a number of times equal to your Rogue level, and gain all expended uses back after a long rest.

Once a creature suffers a snare effect, they cannot suffer another until the current effect on them is ended. The result of the roll creates an effect from the list below:

• 0-2: Crippling Laceration - The target must make a Constitution saving throw equal to 8 + your Dexterity modifier + your proficiency bonus, or have their movement speed reduced to a maximum of 10. At the end of each of their ensuing turns, they may make this save again, losing the effect on a success.
• 3-4: Ensnaring Strike - You have advantage on opportunity attacks against the target until the start of your next turn. 
• 5-7: Staggering Impact - The target must make a Constitution saving throw equal to 8 + your Dexterity modifier + your proficiency bonus. On a failure, they cannot take actions until the end of their next turn, and are knocked prone.

Superior Trailing

Starting at 9th level, your ability to remain unseen by your targets allows you to become all but invisible to them. As a bonus action, you can designate one creature that you can see. Until that creature leaves your sight, or until you use this ability again, you have advantage on Dexterity (Stealth) checks to avoid detection by that creature. If a currently designated creature moves more than half their movement speed on their turn, you may use a reaction to make an opportunity attack against them with a ranged or thrown weapon you are holding.

Tormenting Presence

By 13th level, you become a living nightmare in the minds of your targets. You gain proficiency in Intimidation, and your proficiency bonus is doubled for any ability check you make that uses Intimidation.

As an action, you may attempt to intimidate a creature within 60ft of you currently affected by your Superior Trailing. Make a Charisma (Intimidation) check contested by a Wisdom saving throw by the target. If your roll is equal or higher to theirs, they become frightened of you while they remain the target of your Superior Trailing. On their turn, they may use an Action to make another contested roll of this nature, losing the condition if their roll is equal to or higher than yours.

You can use this ability a number of times equal to your Charisma modifier. You regain all expended uses after a short rest.

No Escape

When you reach 17th level, you are able to cut down targets that attempt to escape you. When you make an opportunity attack, you can use your Sneak Attack against that target even if you don't have advantage on the attack roll, but not if you have disadvantage on it. In combat, you get a special reaction that you can take once on every creature's turn, except your turn. You can use this special reaction only to make an opportunity attack, and you can't use it on the same turn that you take your normal reaction.