Cloak and Dagger

You've honed your skills in the art of misdirection and knife fighting. Criminals and pickpockets typically follow this archetype, but so do rogues who prefer to keep out of harms reach and avoid attention when necessary. In addition to improving your subtly and knife skills, you learn techniques useful for bypassing sentries, dispatching your enemies, and deploying devices you normally couldn't deploy.

Hidden Blade

Starting at 3rd level, when you take the attack action with a dagger or dart, you simultaneously strike the same target with a hidden blade or dart.

When determining the damage you do for an attack you make with a dagger or dart, roll an additional 1d4 and add it to the total. The amount of extra damage increases as you gain levels in this class, 2d4 at 5th level, 3d4 at 11th level and 4d4 at 17th level.

You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you make a weapon attack with a dagger or a dart, and you don't have disadvantage. All the other rules for Sneak Attack still apply to you.

Misdirection

When you choose this archetype at 3rd level, you gain the ability to blend into crowds and direct attention away from yourself. 

When you have an ally or non hostile humanoid within 5ft of you, and no enemies within 5ft of you, you can Hide as a bonus action even if you are being directly observed. 

Tricks of the Trade

Starting at 9th level, you have obtained and learned to use specialized tools to assist you in your subterfuge and combat. 

You gain proficiency with blowguns. Additionally, attacking at long range doesn't impose disadvantage with thrown weapon attacks using daggers, nor ranged weapon attacks using darts.

You have learned 3 tricks of the trade, each of which you can use once per short rest. (You gain an additional use of each at 17th level)

Smoke Bomb: As an action, you can throw a smoke bomb up to 60ft at a target location you can see. A cloud of thick smoke pours out in a 30-foot radius sphere from the target location. The smoke's area is heavily obscured, but you can see normally through the smoke. Targets of your choice that start their turn within the smokes area of effect can take the Hide, Disengage and Dash action as a bonus action. The smoke cloud dissipates after 1 minute or until a strong wind (such as one created by Gust of Wind) disperses it.

Sleeping Dart: As an action, you produce a magical blowgun and make a ranged weapon attack against a target you can see. A creature hit with this attack takes no damage, but is instead affected by the Sleep spell. The DC equals 8 + your Proficiency bonus + your Wisdom modifier. This attack makes no sound, and if you use this ability while you are hidden you remain hidden.

Fire Cracker: As an action, you can throw a small pouch of blasting power up to 60ft at a targeted location you can see. The pouch ignites on impact, producing light and an audible noise that can be heard from up to 60ft away. Immediately after using this ability, you and any allies within 15ft of you gain advantage on the next Stealth check you or they make to hide or move silently. Additionally, creatures who can hear or see the fire cracker have disadvantage on their next Perception check to detect you and your allies, as their attention is drawn towards the small explosive device. 

Kill Streak

By 13th level, you have learned new ways to utilize your quick reflexes to chain multiple attacks together and produce deadly results. 

Dart Opportunity Attack. When a creature moves outside the normal range of your dart's attack range (20ft), you can use your reaction to make a ranged opportunity attack against that creature with a dart. 

Reactive Sneak Attack. When you hit a target with a sneak attack, you can use your reaction to immediately make another weapon attack. If this reaction attack hits, you can apply sneak attack again.

Bonus Sneak Attack. When you land a critical hit or you kill a target with your sneak attack, you can use a bonus action to immediately make another weapon attack. If this bonus action attack hits, you can apply sneak attack again. 

Master Stroke

When you reach 17th level, you have become a master of the Cloak and Dagger. You gain an additional use of each of your Tricks of the Trade abilities and they gain additional functionality.

Smoke Bomb. You and your allies can see normally through the Smoke Cloud's area of effect. Enemies that start their turn within, or enter the smoke cloud's area of effect on their turn, must make a Constitution saving throw. On a failed save, the target has the Stunned condition until the start of your next turn. On a successful save, the target’s Speed is halved until the start of your next turn. The smoke is unnaturally heavy and can no longer be dissipated by strong winds.

Sleep Dart. If you successfully hit a target with a sleep dart, but the target succeeds on its saving throw to resist the sleep effect, the dart inflicts poison damage equal to your sneak attack damage to the target. This poison damage ignores resistances. 

Fire Cracker. When you use your Fire Cracker ability, you can choose to instead throw a Blast Bomb. 

Blast Bomb. Each creature in a 20-foot-radius sphere centered on a point you can see within 60ft must make a Dexterity saving throw against a DC of 8 + your Proficiency bonus + your Wisdom modifier. A target takes force damage equal to your sneak attack damage on a failed save, or half as much damage on a successful one.