Lucky Rogue

Pursued by a mob of  defeated gamblers across a congested city's rooftops, a fleeing rogue barely makes an impossible jump to escape with an impossibly large sum of gold. Blindfolded and drugged, an escaping prisoner somehow manages to hurl a dagger directly through the eye of his pursuing captor. A stumbling halfling misses an arrow, only to trigger a landslide that leaves her party unscathed but the hostile Ettin entombed. Some rogues find that their luck is unmatched by an extreme margin. They are able to survive the most dangerous encounters and even profit when the odds are stacked against them. Such rogues that are intrinsically connected to fate find their destinies guiding them to lives as adventures, and are equally likely to survive as living legends as they are to be left to die a gruesome death.

Gambler's Folly

When you choose this archetype at 3rd level, you gain proficiency in the Sleight of Hand or Deception if you don't already have it. You also gain proficiency with any two gaming kits of your choice.

All or Nothing

Starting at 3rd level, you gain a pool of luck points equal to your proficiency bonus that replenish after a long rest. Once per turn, you may spend a luck point on an attack roll, ability check, or saving throw. Instead of rolling a d20, flip a coin.

For ability checks and saving throws, treat a heads as a 20 and a tails as a 1 and add the appropriate modifiers. For attack rolls, treat a heads as a critical hit and a tails as a miss.

If this feature is used on an attack roll, all additional effects that would normally be applied to the attack or its damage roll after the result of an attack is known—such as Divine Smite, Stunning Strike, Combat Inspiration, Stroke of Luck, and Path to the Grave—must be announced before the coin is flipped. Each effect is expended regardless of the result of the roll, but only can only be applied on a hit. Sneak Attack can be applied an attack roll that uses this feature. If Sneak Attack is announced and the attack misses, Sneak Attack cannot be applied to any attack roll for the rest of the turn.

Attacks rolls, saving throws, and ability checks that use this feature cannot be affected by any  effect that would modify the result of a roll, such as Guidance, Bardic Inspiration, Battlemaster Maneuvers, Reliable Talent, or the Sharpshooter feat. Additionally, Advantage and Disadvantage are disregarded when applied to a roll that uses this feature.

Examples:

• If a Grave Cleric uses Path to the Grave and the Lucky Rogue does not call the use of this ahead of time, the damage vulnerability cannot be applied to this attack, but still can be applied to the following attacks. If the Lucky Rogue does call Path to the Grave but the attack misses, the curse would vanish, and the damage vulnerability could not be applied to subsequent attacks. If the Lucky Rogue does call Path to the Grave and the attack hits, the damage vulnerability would apply and the curse would vanish.
• A Lucky Rogue with the Sharpshooter feat could not benefit from the +10 damage as a result of the Sharpshooter feat if this class feature was used during the attack.
• A Lucky Rogue/Paladin multiclass would have to declare the smite first, and then expend the spell slot regardless of whether or not the attack actually hit. If the attack did hit, the smite damage would be applied like a normal critical hit.
• A Luck Rogue could use the College of Valor Bard's Combat Inspiration, but that would have to be declared before the coin was flipped.
• Any Battlemaster Maneuver that would add damage to the damage roll must be declared before the attack was made, and the superiority dice is spent regardless of whether or not the attack actually hit.
• The attack would still benefit from the dueling fighting style as would be applied for an ordinary critical hit.

 

Lucky Copper

You have learned to apply your luck to grant you helpful information. Once per long rest, you may spend a luck point to divine the answer to a question that can be answered with a yes or a no by flipping a coin. A heads means yes, and a tails means no. In a case where a one word answer may be misleading, the coin may spin before coming to rest on its side or may roll away and become lost, implying a number of ambiguous responses. 

Luck of the Draw

Starting at 13th level, you find your luck leading you to become aware of things you otherwise wouldn't notice, a chance wind blowing in the directions of enemies waiting for ambush, or glint of light rebounding off a friend's blade to reveal the silhouette of a creature lurking in the dark. You may spend a luck point to grant a +5 bonus to your initiative or to prevent you from being surprised by an enemy.

Additionally, during the first round of combat, you may use your reaction to spend a luck point to impose disadvantage on an attack roll made against you.

Inexorable Fate

Starting at 17th level, the world seems to bend and weave around you. Once per turn, immediately after you make a critical hit, you may make additional attack. This attack can benefit from your Sneak Attack even if you have already used it this turn.