Highwayman

Some rogues are called "swashbuckling rakes" by romanticizing nobles.  Others are called "bandits."  Rogues who emulate this archetype are the latter.  Robbers, thugs, muggers and brigands, Highwaymen are experts at forcibly parting folks from their livelihood.  Be it through violence or the threat of violence, Highwaymen know how to find their way in the world by taking from those less powerful.  Highwaymen are kings of the places where might is the only rule of law that matters.  The grungy back alley and the dusty back road are both the Highwayman's domain.  While some Highwaymen are reformed and use their skills for a new purpose, most are miscreants, or are at very least one bad day away from turning back to their old ways.

Stickup Expert

Starting when you choose this archetype at 3rd level, when you make an attack targeting a humanoid within 30 feet of you using a ranged weapon or a dagger, you score a critical hit on a roll of 19-20.  When you score a critical hit with a dagger against a creature within 5 feet of you, you can roll an additional 6d4 when determining the extra piercing damage the target takes.

If your Dungeon Master uses the rules on firearms in the Dungeon Master's Guide and your rogue has been exposed to the operation of such weapons, your rogue is proficient with pistols.  Being within 5 feet of a hostile creature doesn't impose disadvantage on your weapon attacks made using ranged weapons that lack the heavy property.

Bandit's Sense

Starting when you choose this archetype at 3rd level, you can add your proficiency bonus to initiative rolls.

Robber's Eye

At 9th level, you are a seasoned veteran when it comes to gauging whether or not a potential target is easy prey.  If you spend at least 1 minute observing a creature or group of creatures outside of combat, you can learn certain information about their capabilities and whether they will be compliant or not.  The DM tells you one of the following of your choice:

• If a creature is inclined to surrender if threatened.  The DM tells you certain, likely, unlikely, impossible or uncertain.
• The lifestyle of a humanoid creature.  The DM tells you wretched, squalid, poor, modest, comfortable, wealthy, aristocratic, or none of these.
• If a creature's CR is greater than half your level, greater than your level, or neither
• If a creature has class levels, and if the creature's total number of class levels exceeds half yours
• If a creature is proficient in the Perception skill

If you spend at least 10 minutes observing, the DM tells you one of the following:

• Which creature or creatures are the leadership of the group
• The purpose of a group of three or more creatures.  The DM tells you commerce, war, banditry, law enforcement, hunting, relocation, or none of those.

Hostage

By 13th level, you pose a grave danger to those you gain the upper hand against in combat.  When you successfully grapple a creature, you can take the ready action as a bonus action.  When you hit with an attack with a dagger or ranged weapon against a Medium or smaller creature within 5 feet of you that is grappled or incapacitated, you can turn that hit into a critical hit.  Once you have used this feature to turn a normal hit into a critical hit, you cannot do so again until you have completed a short or long rest.

Lethal Eye

Starting at 17th level, you are a master of striking creatures where they're vulnerable.  When you make an attack targeting a creature within 30 feet of you using a ranged weapon or a dagger,  you score a critical hit on a roll of 19-20.  If the target is a humanoid, you score a critical hit on a roll of 17-20.  If the target is a humanoid with a challenge rating less than half your level, you score a critical hit on a roll of 13-20.