Silent Conniver

Based heavily on The Silent from Slay the Spire.

Silent Connivers are especially deadly rogues who specialize in poisoning their foes with vile concoctions and ensuring you always have the upper hand, even if the enemy doesn’t know it.

Adroit Accuracy

At level 3, your accuracy is unparalleled, and you fight with a bit of magic.

Adroit Accuracy: You gain the Archery fighting style, and this bonus applies to thrown weapons as well. Your thrown weapons have a minimum damage die of 1d6.

After a long rest, you may assign one weapon to return to your hand whenever it is thrown, or arrows from a quiver to return to the quiver when fired.

Thrown weapons benefit from the Crossbow Expert feat’s passive of not imposing disadvantage on thrown attacks made on enemies within 5ft.

Cunning Action: Accuracy: You may use your Bonus Action during your turn to give you advantage on your next attack.

Poisoner’s Implements

Also at level 3, you gain access to poisons you can apply to your weapons.

Poisoner’s Implements: You become proficient with Poisoner’s Kits. 

When you finish a long rest, choose a weapon. You coat this weapon in a specially created poison that lasts the whole day. The poison is magical in nature, costs nothing to craft, and can be cured like any other poison.

Any time you attack an enemy with this weapon, they are inflicted with Silent Poison, which causes them to take 1d4 poison damage at the start of their turn for the rest of combat or until cured. This stacks twice, for up to 2d4 poison damage at the start of their turn.

In addition, when you Sneak Attack someone inflicted with Silent Poison, you deal the poison damage that is currently applied to them. (Ex: Sneak Attacking someone you’ve applied 2 stacks on will roll 2d4 poison damage in addition to your sneak attack damage. These dice are also doubled if you critically hit.)

Outmaneuver

At level 9, you gain a few tricks up your sleeve…

Outmaneuver: When Initiative is rolled, you can use your Reaction to immediately make an attack from where you’re standing (this may be a Sneak Attack if the conditions are right), and add +3 to your Initiative roll. 

Deadly Poison: You can now stack Silent Poison on an enemy up to 3 times.

One Thousand Cuts: After making a ranged attack with your action, you can choose to use your Bonus Action to make another ranged attack that always hits, but only deals damage equal to your Dexterity modifier. This attack can apply Silent Poison.

Escape Plan

Escape Plan: After you finish a long rest, you craft two poisonous smoke bombs. 

You can use these at any time you wish for a Bonus Action. Upon use, you apply one stack of Silent Poison and Blindness to all enemies within 10ft of you. The Blindness lasts for one round. 

You may then move as though you had used Disengage.

If your DM permits, you may carry any extra Escape Plans into the next day. Otherwise, they become nonfunctional after you finish a long rest.

Tuck and Roll: When you use Uncanny Dodge, you can further reduce damage taken by your Dexterity modifier plus your Constitution modifier.

Vile Poison

Catalyst: Your attacks that use your action will always deal additional Silent Poison damage to enemies with stacks of the poison, whether or not it’s a Sneak Attack.

You can stack Silent Poison up to four times now.

Malaise: Once per long rest, when you successfully attack an enemy, you can give that enemy vulnerability to poison damage for two rounds. This condition can be cured with a Lesser Restoration spell.

Wraith Form: When you use your Escape Plan, you become Invisible for 1 turn.