User:ArcaediusX/The Shadowmaster Rogue

The Shadowmaster

Rogue Archetype

Thunder rumbles outside as the noble drops to the floor from a sudden dagger strike in the dark. Outside, her assailant casually mingles with the other members of nobility as he works his way through the crowded parlor and eventually outside the manor. In many ways, the Shadowmaster is your typical, silent assassin. Yet, the difference in the attention to details and their handling of people is what often sets Shadowmasters into a class of their own. Often, these individuals are nobles or in the employ of such, and have learned how to work the ins and outs of high-class society. When one family begins to make power plays that threaten another, often time it is Shadowmasters that will be called to handle the situation through either defamation, humiliation, or - if necessary - extermination. As one of these silent stalkers, your Rogue has chosen a path that emphasizes putting on a proper face and learning to navigate both the shadows and the world in the light.

Features

A Knife in the Dark

When you choose this archetype at 3rd-level, you specialize in the efficient dispatch of your targets and enemies with the easily-concealable dagger and to act with greater agility.

Whenever you make a weapon attack that uses a magical or non-magical dagger, you roll 1d6 for damage, instead of the usual 1d4, and apply modifiers as normal. Additionally, any ranged attack you make using a dagger has a short and long range of 40 and 80 feet, respectively.

You gain a bonus to Initiative rolls equal to your Intelligence modifier (minimum of +1).

With A Silvered Tongue

Beginning at 3rd-level, you have learned how to insert yourself into wider social circles and smooth talk your way through conversations.

You learn two languages of your choice. You gain proficiency in Deception and Persuasion, if you do not already have it. For each one that you already possess, you gain proficiency in one skill of your choice instead.

Lastly, you may add Deception and Persuasion to the list of your chosen skills using your Expertise feature, unless they already benefit from such an ability or similar effect.

Swift and Silent

At 9th-level, your walking speed increases by 10'. Additionally, you now add your Intelligence modifier as a bonus to any Dexterity (Stealth) checks you make.

Deceptive Feint

Starting at 13th-level, you have learned to misdirect your intentions in the heat of combat.

When you take the Attack action on your turn, you may immediately use a bonus action (if available) to make a Charisma (Deception) roll against your target's Wisdom (Insight). Upon a success, you gain advantage on the attack if you did not already have it. If you already had advantage, then treat the attack as an automatic critical hit; calculating damage and sneak attack damage accordingly.

You may use this ability a number of times equal to your Charisma modifier and you regain all uses upon completing a long rest.

Checkmate

Starting at 17th-level, your mastery of tactics and strategic movements allow you to strike unsuspecting targets with devastating effectiveness.

On your first turn of each combat, you gain the following benefits:

• You may make one additional Attack action this turn.
• You may use two Bonus Actions this turn, including using your Cunning Action twice for the same action.
• You may deal Sneak Attack damage twice this turn, regardless of whether you have advantage, but only once per target.

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