Ruffian

As a Ruffian you are well-versed in the use of underhanded tactics to achieve the upper hand in combat. You've honed your martial skills through your experiences trying to make a place for yourself in a violent and uncaring world, and have come to understand that there is no room for honour when it comes to matters of survival. Unscrupulous mercenaries and underground pit fighters will often follow this archetype, although it may include any adventurer who has had to learn how to fight from the school of hard knocks as opposed to formal training.

Any Tool Will Do

At 3rd level you have become adept at using whatever tools are available to get the job done. You gain the following benefits:

You are proficient with all improvised weapons.

You may add Sneak Attack dice to damage rolls for any weapon you are proficient with, regardless of whether they also have the finesse or ranged property. This includes unarmed strikes and improvised weapons.

Additionally, as a free action you may pick up and wield a small sized object you can hold in one hand as an improvised shield. Wielding an improvised shield increases your Armor Class by 2. Objects you may use are at the DM's discretion, however suggested examples of improvised shields include a chair, a bucket or a cloak which you are not wearing. You lose the benefits of this shield when you are incapacitated.

You can benefit from only one shield (be it improvised or otherwise) at a time.

Opportunist

At 3rd level, you may use a bonus action to prepare an attack against a creature you can see. Whenever the creature takes damage before your next turn, you may use your reaction to make a weapon attack against them with a weapon you are currently holding.

If an attack triggered in this way is eligible for Sneak Attack damage you may only roll half the number of Sneak Attack dice for your level (rounded up). For example, a 5th level Ruffian who uses this feature and can add Sneak Attack dice to the damage roll may only add 2d6.

Stunning Attack

Starting at 9th level, you have learnt how to temporarily stun your opponents by targeting their weak spots. When you hit a creature with an attack which meets the conditions for the Sneak Attack feature you may attempt to stun them instead of dealing the additional damage granted by that feature. Instead, the creature must succeed on a constitution saving throw or be stunned until the end of their next turn. The DC for this check is determined by rolling the Sneak Attack dice you would have rolled and halving the result (rounded up). For example, the number of Sneak Attack dice you may roll is still doubled if the weapon attack which caused it was a critical hit.

You may choose to use this feature after knowing the result of an attack roll but before you roll your weapon and Sneak Attack damage dice.

Art of Deception

At 13th level, when you use the Uncanny Dodge feature you may choose to feign a serious injury. As part of the same reaction you may make a Deception (Charisma) or Performance (Charisma) check. You may also choose to immediately go prone as part of this reaction to make this check with advantage.

Any creature whose Passive Insight is less than this check believes you to no longer be an immediate threat to their safety, although they may still choose to attack you or use an action to make an Insight (Wisdom) check with DC equal to 8 + your proficiency bonus + your charisma modifier. The next attack or ability check you make against a creature under the effect of this feature has advantage.

This effect ends for all creatures who can see you after you make an attack or cast a spell.

Improved Opportunist

When you reach 17th level, you have mastered the art of attacking creatures when they are down. Attacks you make using the Opportunist feature have advantage and may use the full number of Sneak Attack dice available for your Rogue level.