Scoundrel

Rogue Subclass: Scoundrel

Level 3: Dirty Tricks

You’re adept at surprising targets using unexpected methods.

Bag of Tricks: You gain proficiency with improvised weapons; and you keep small bags various materials on your person such as ash, ball berrings, nails, pepper, rubble, salt, shattered glass, wood splinters, and other seemingly random material to use in combat. You can carry up to your Rogue Level of these bags on your person and ignore weight or space requirements, and you can replace used bags with materials you find in the area during a Short Rest without cost.

On your turn, during combat, you may use your Cunning Action and use one bag in your Bag of Tricks to damage or potentially Hinder opponents. Any opponent within a15-foot cone from you, in a direction you choose, must succeed a Dexterity Saving Throw or take your Sneak Attack Dice in damage and suffer a Disadvantage on any attack or skill check until the start of your next turn.

Opponents who succeed the Saving Throw take half damage and do not suffer Disadvantage, and the DC to save is 8 + your proficiency bonus + your charisma modifier.

Stunning Strikes. During the first round of each combat, you have Advantage on attack rolls against any creature that hasn’t taken a turn. If your Sneak Attack hits a target during that round, the target must make a Constitution Saving Throw or be Stunned until the end of your next turn.

Level 3: Master Schemer

You gain proficiency with the Deception Skill if you don't already have the skill, or you gain Expertise with the Deception Skill if you do.

You also gain an Advantage to any Investigation or Perception Skill Check when attempting to gather information.

Level 9: Infiltration Expertise

You are expert at the following techniques that aid your infiltrations.

Masterful Mimicry. You can unerringly mimic another person’s speech, handwriting, or both if you have spent at least 1 hour studying them.

Master of Disguise. You gain Proficiency with a Disguise Kit if you do not have it, and you gain the ability to use a Disguise Kit to cast the Disguise Self Spell and perfectly resemble another humanoid creature that you have studied for the duration of the spell. Anyone attempting to see through the illusion must make an Intelligence Saving Throw at a Disadvantage to do so. The DC for the saving throw is 8 + your charisma modifier + your proficiency bonus.

Level 13: Scoundrel's Luck

You can change any D20 die roll for any creature you can see within 120 feet or for yourself into a 20 or into a 1 with a wiley grin and a sly wink.

You must take a Short Rest before using this ability again.

Level 17: Contingency Plan

When you run out of luck, you always have a way out. You deceive, intimidate, or persuade a wizard to create a Teleportation Circle inside of your Rogue's Bastion or some other safe location as well as a special trinket that is magically linked to that Teleportation Circle and that you keep on your person. If things go horribly wrong, and you are not Incapacitated, you may activate your trinket and open a portal from your present location to the Teleportation Circle and make a hasty escape.

Level 3: Dirty Tricks

Dirty Tricks

You’re adept at surprising targets using unexpected methods and gain Proficiency with improvized weapons.

Bag of Tricks: You keep small bags various materials on your person such as ash, ball berrings, nails, pepper, rubble, salt, shattered glass, wood splinters, and other seemingly random material to use in combat. You can carry up to your Rogue Level of these bags on your person and ignore weight or space requirements, and you can replace used bags with materials you find in the area during a Short Rest without cost. Or, you may pick up anything at hand that might be used as an Improvised weapon such as a bottle, chair, mug, etc..

On your turn, during combat, you may use your Cunning Action and use one bag in your Bag of Tricks or improvised weapon to damage or potentially Hinder opponents. Any opponent within a15-foot cone from you, in a direction you choose, must succeed a Dexterity Saving Throw or take your Sneak Attack Dice in damage and suffer a Disadvantage on any attack or skill check until the start of your next turn.

Opponents who succeed the Saving Throw take half damage and do not suffer Disadvantage, and the DC to save is 8 + your proficiency bonus + your charisma modifier.

Master Schemer

You gain proficiency with the Deception Skill if you don't already have the skill, or you gain Expertise with the Deception Skill if you do.

You also gain an Advantage to any Investigation or Perception Skill Check when attempting to gather information.

Master of Disguise

You are expert at the following techniques that aid your infiltrations.

Masterful Mimicry. You can unerringly mimic another person’s speech, handwriting, or both if you have spent at least 1 hour studying them.

Master of Disguise. You gain Proficiency with a Disguise Kit if you do not have it, and you gain the ability to use a Disguise Kit to almost perfectly resemble another humanoid creature that you have studied for one hour. Anyone attempting to see through the your disguise must make an Perception Skill Check at a Disadvantage.

The DC for the Skill Check is 8 + your charisma modifier + your proficiency bonus.

Scoundrel's Luck

You can change any D20 die roll made by you or someone you can see into a 20 or into a 1 with a wily grin and a sly wink. You must take a Short Rest before using this ability again.

 

Contingency Plan

When you run out of luck, you always have a way out. You deceive, intimidate, or persuade a wizard to create a Teleportation Circle inside of your Rogue's Bastion or some other safe location as well as a special trinket that is magically linked to that Teleportation Circle and that you keep on your person. If things go horribly wrong, and you are not Incapacitated, you may activate your trinket and open a portal from your present location to the Teleportation Circle and make a hasty escape.