Base Class: Rogue
In the veiled realm between twilight and obscurity, there exists an elite order known as the Shadowguard. Masters of clandestine arts and protectors of the realm's highest echelons, these elusive warriors traverse the shadows with the grace of wraiths, their every movement cloaked in mystery. In times of dire need, they vanish from sight, leaving nothing but a whisper of a chilling breeze. Their reappearance is swift and decisive, catching adversaries unaware. In the pinnacle of their mastery, a Master Infiltrator, they transcend mere mortal boundaries, teleporting effortlessly through the very essence of shadows. To encounter a Shadowguard is to witness a living manifestation of the night itself – a guardian, a phantom, a sworn protector of the realm's noblest. They are the shadowed sentinels, the unsung heroes in the realm of darkness, their allegiance pledged to the safeguarding of the aristocracy from the unseen threats that lurk in the periphery.
Bonus Proficiencies
Shadow Guard 3rd Level Feature
At the third level, your training as a fighter begins to bleed through and grant you proficiency in medium armor, martial weapons, and disguise kits.
Umbral Vision
Shadow Guard 3rd Level Feature
Starting at the third level, your eyes have adapted to the darkest parts of the world. You can see normally in total darkness so long as it is nonmagical up to 30 feet.
Shadow Strike
Shadow Guard 3rd Level Feature
At 3rd level, you gain the ability to step into the shadows. As a bonus action, you can teleport up to 30 feet to an unoccupied space you can see that is in dim light or darkness. You then have advantage on the first attack you make before the end of the turn. You can use this ability a number of times equal to your charisma modifier before needing to take a long rest.
The range of your teleportation increases to 60ft at level 9, 90ft at level 15.
Dreadful Aspect
9th Level Shadow Guard Feature
Your presence alone terrifies even the bravest. As an action, you can choose a number of creatures equal to your charisma modifier and make a CHA (Intimidation) to be contested by a WIS (Insight) check. If you fail the check, nothing happens.
If you succeed on the check and the creature is hostile to you, it becomes frightened by you, terrified that you will come and strike it from any shadow. This effect applies even if it leaves your line of sight, in which case a creature can still move. This effect lasts for 1 minute, or until you are more than 120ft from the target, or until you fall unconscious.
If you succeed on the check and the creature isn't hostile to you, it is instead charmed by you for 1 minute. While charmed, it will try it's utmost to not incur your wrath, assuming it has the intelligence to make that judgement. This effect ends immediately if you or your companions do anything to harm it.
Assassin's Strike
13th Level Shadow Guard Feature
Your mastery of weapons and innate skill in killing has given you the ability to target the weakest points on your enemy.
Once per turn, when you have advantage on an attack roll, you may choose to forgo the advantage roll. If you do and the attack hits, the target must make a CON saving throw DC of 8 + DEX Modifier + Proficiency Bonus. On a failure, the hit automatically becomes a critical hit and benefits from sneak attack. On a success, the attack lands as normal. This can only be done a number of times equal to your DEX modifier, and replenishes on a short or long rest.
One With The Shadows
17th Level Shadow Guard Feature
At 17th level, you have become one with the shadows. While you are standing in dim light or darkness, you can become invisible at will. You are classified as an unseen attacker and gain advantage on Dexterity (Stealth) checks to perceive your location. This feature is only lost when you leave the area of effect, or choose to turn it off.