Rogue of the Assassin Archetype

Feat progression

1. L4Alert — +1 init, advantage on DEX saves
2. L8Lucky — 3 luck points
3. L12Sharpshooter — -5 attack, +10 damage

Loremaster’s notes

The Assassin Rogue is the "I kill people in their sleep" build. Assassinate (level 3): any attack roll against a creature that hasn't taken a turn in combat yet (surprise round or first-round-only target) is a critical hit. So your level 1 sneak-attack-dice × 2 = 2d6 doubled to 4d6 at level 1, scaling to 10d10 doubled to 20d10 at level 19. Infiltration Expertise (level 9) lets you forge documents and adopt a disguise over 7 days of work. 1 hour to change back to your "default" identity. Death Strike (level 17) is the cap: if you hit and damage a surprised creature with a melee weapon, it must make a CON save (DC 8 + DEX mod + prof) or have its hit point maximum reduced to 0. One-shot boss. But you need surprise to land it. Race: Half-Elf for CHA +2 (and the Mask of the Wild doesn't help here), Halfling for Stealth synergy, or Aasimar for the +2 CHA and free CHA-mod-extra-damage-1/day.