The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn't notice a threat is surprised at the start of the encounter.
If you're surprised, you can't move or take an action on your first turn of the combat, and you can't take a reaction until that turn ends. A member of a group can be surprised even if the other members aren't.
In the context of an assassin rogue, the rogue (if alone) needs to stealth and roll higher than the passive perception of the intended target. (Or beat the target's roll if the target is on alert for some reason.) The rogue then needs to attack the unsuspecting target in the first round of combat.
If the rogue is with a party and the rest of the party did not stealth, then no enemy will have the surprised condition.
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what does surprised mean, in the context of an assassin rogue
because I have no clue what this means
Rules As Written:
In the context of an assassin rogue, the rogue (if alone) needs to stealth and roll higher than the passive perception of the intended target. (Or beat the target's roll if the target is on alert for some reason.) The rogue then needs to attack the unsuspecting target in the first round of combat.
If the rogue is with a party and the rest of the party did not stealth, then no enemy will have the surprised condition.