Cunning Captains follow in the footsteps of the greatest rogue of all time, Odysseus. You command allies while relying on wit, preparation, and quick thinking to overcome impossible odds. You know that outsmarting your opponent is the best path to victory over pure brute strength. Whether leading companions through perilous adventures, devising clever stratagems in the heat of battle, or turning an enemy’s strength against them, you prove that a sharp mind is the deadliest weapon of all.
Skirmish Commander
Level 3: Your experience has expanded your options. You learn techniques that are fueled by special dice called Skirmish Dice.
Techniques. You learn three techniques of your choice from the “Technique Options” section later in this subclass’s description. Many techniques enhance an attack in some way. You can use only one technique per attack. You learn two additional techniques of your choice when you reach Rogue levels 9, 13, and 17. Each time you gain Rogue levels, you can replace one technique you know with a different one.
Skirmish Dice. You have four Skirmish Dice, which are d8s. A Skirmish Die is expended when you use it. You regain all expended Skirmish Dice when you finish a Short or Long Rest. You gain an additional Skirmish Die when you reach Rogue levels 9 (five dice total) and 13 (six dice total).
Saving Throws. If a technique requires a saving throw, the DC equals 8 plus your Dexterity or Charisma modifier (your choice) and Proficiency Bonus.
Battle Experience
Level 3: You have honed your martial prowess and gain a Fighting Style feat of your choice. Whenever you gain a Rogue level, you can replace the feat you chose with a different Fighting Style feat.
Additionally, you gain training with Medium armor and Shields.
Hardened Combatant
Level 9: The many battles you’ve endured made you strong, granting you the following benefits:
Extra Attack. You can attack twice instead of once whenever you take the Attack action on your turn.
Improved Skirmish Commander. Your Skirmish Die becomes a d10.
Medium Armor Legend. While you’re wearing Medium armor, you can add your whole Dexterity modifier to your AC if you have a Dexterity score of 16 or higher.
Crafty Stratagem
Level 13: When you deal Sneak Attack damage, you regain one Skirmish Die.
Ultimate Skirmish Commander
Level 17: Your Skirmish Die becomes a d12.
Technique Options
The techniques are presented here in alphabetical order.
Ambush.
When you or an ally within 30 feet make a Dexterity (Stealth) check or an initiative roll, you can expend one Skirmish Die and add the die to the roll, provided you aren’t incapacitated.
Commander’s Strike.
When you take the Attack action on your turn, you can replace one of your attacks to direct one of your companions to strike. When you do so, choose a willing creature who can see or hear you and expend one Skirmish Die. That creature can immediately use its Reaction to make one attack with a weapon or an Unarmed Strike, adding the Skirmish Die to the attack’s damage roll on a hit.
Concussion Strike.
When you hit a creature with an attack roll, you can expend one Skirmish Die to attempt to concuss the target. Add the Skirmish Die roll to the attack’s damage roll. The target must succeed on a Constitution saving throw or suffer Disadvantage on its next saving throw before the end of your next turn. Creatures that are immune to Exhaustion automatically succeed on this saving throw.
Cunning Presence.
When you make a Charisma (Deception, Intimidation, Performance, or Persuasion) check, you can expend one Skirmish Die and add that die to the roll.
Daredevil Athlete.
When you make a Strength (Athletics) check or a Dexterity (Acrobatics) check, you can expend one Skirmish Die and add that die to the roll.
Disarming Attack.
When you hit a creature with an attack roll, you can expend one Skirmish Die to attempt to disarm the target. Add the Skirmish Die roll to the attack’s damage roll. The target must succeed on a Strength saving throw or drop one object of your choice that it’s holding, with the object landing in its space.
Distracting Strike.
When you hit a creature with an attack roll, you can expend one Skirmish Die to distract the target. Add the Skirmish Die roll to the attack’s damage roll. The next attack roll against the target by an attacker other than you has Advantage if the attack is made before the start of your next turn.
Effusive Distraction.
As a Bonus Action, you can expend one Skirmish Die to allow an ally to escape detection. Choose one willing creature within 30 feet. That creature can take a Reaction to move up to half its Speed without provoking an Opportunity Attacks. If it ends its turn in a location that is Heavily Obscured or behind Three-Quarters Cover or Total Cover, it can immediately take a Hide action. Add the Skirmish Die to its Dexterity (Stealth) check.
Feinting Attack.
As a Bonus Action, you can expend one Skirmish Die to feint, choosing one creature within 5 feet of yourself as your target. You have Advantage on your next attack roll against that target this turn. If that attack hits, add the Skirmish Die to the attack’s damage roll.
Goading Attack.
When you hit a creature with an attack roll, you can expend one Skirmish Die to attempt to goad the target into attacking you. Add the Skirmish Die to the attack’s damage roll. The target must succeed on a Wisdom saving throw or have Disadvantage on attack rolls against targets other than you until the end of your next turn.
Grappling Strike.
When you hit a creature with a melee attack on your turn, you can expend one Skirmish Die to attempt to grapple the target. Add the Skirmish Die to the attack’s damage roll. Then you may take a Bonus Action to make an Unarmed Strike against the target.
Guiding Strike.
When you hit a creature with an attack roll, you can expend one Skirmish Die to attempt to help your disabled ally strike as well. Choose a willing creature that can hear you and that has the Blinded condition. Before the start of your next turn, add the Skirmish Die to the next attack roll made by the chosen creature against the target of your attack roll.
Inspiring Word.
As a Bonus Action, you can expend one Skirmish Die to embolden an ally with renewed vigor. Choose an ally of yours within 30 feet of yourself who can hear you. They can spend one of their Hit Point Dice to regain Hit Points. Roll the Hit Point Die and add the ally’s Constitution modifier and the Skirmish Die to it. They regain Hit Points equal to the total (minimum of 1 Hit Point).
Maneuvering Attack.
When you hit a creature with an attack roll, you can expend one Skirmish Die to maneuver one of your comrades into another position. Add the Skirmish Die roll to the attack’s damage roll, and choose a willing creature who can see or hear you. That creature can use its Reaction to move up to half its Speed without provoking an Opportunity Attacks from the target of your attack.
Menacing Attack.
When you hit a creature with an attack roll, you can expend one Skirmish Die to attempt to frighten the target. Add the Skirmish Die to the attack’s damage roll. The target must succeed on a Wisdom saving throw or have the Frightened condition until the end of your next turn.
Parry.
When another creature damages you with an attack roll, you can take a Reaction and expend one Skirmish Die to reduce the damage by the number you roll on your Skirmish Die plus your Dexterity or Charisma modifier (your choice).
Precision Attack.
When you miss with an attack roll, you can expend one Skirmish Die, roll that die, and add it to the attack roll, potentially causing the attack to hit.
Rally.
As a Bonus Action, you can expend one Skirmish Die to bolster the resolve of a companion. Choose an ally of yours within 30 feet of yourself who can see or hear you. That creature gains Temporary Hit Points equal to the Skirmish Die roll plus half your Rogue level (round down).
Riposte.
When a creature misses you with an attack roll, you can take a Reaction and expend one Skirmish Die to make a attack roll with a weapon or an Unarmed Strike against the creature. If you hit, add the Skirmish Die to the attack’s damage.
Steadying Word.
As a Bonus Action, you can expend one Skirmish Die to instill courage in a companion. Choose an ally of yours within 30 feet of yourself who can see or hear you. If that creature has the Charmed or Frightened conditions they can make a Wisdom saving throw against the same DC that imposed the condition. Add the Skirmish Die to their saving throw roll. If they succeed they no longer have the Charmed or Frightened conditions.
Tactical Assessment.
When you make an Intelligence (History or Investigation) check or a Wisdom (Insight) check, you can expend one Skirmish Die and add that die to the ability check.
Trip Attack.
When you hit a creature with an attack roll using a weapon or an Unarmed Strike, you can expend one Skirmish Die and add the die to the attack’s damage roll. The target must succeed on a Strength saving throw or have the Prone condition.
Tumbling Attack.
You can expend a Skirmish Die to tumble past an enemy. During this turn you can move through any creature’s space as if it were an ally. Add the Skirmish Die to the damage of the next attack you make this turn against a creature whose space you moved through.
Wiley Strike.
When you deal Sneak Attack damage and add a Cunning Strike effect you can expend Skirmish Dice instead of removing Sneak Attack damage dice as the cost.
