Assassin Rogues get the 'Assassinate' skill which states:
Assassinate
Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.
Now, Bugbears have this Racial Trait:
Surprise Attack
If you hit a creature with an attack roll, the creature takes an extra 2d6 damage if it hasn’t taken a turn yet in the current combat.
Therefore, I ask, if you played a Bugbear Assassin Rogue, would this mean that if you attacked a creature who had yet to take their turn in combat yet, would that then count as a 'Surprise Attack' for the Rogue Assassinate Skill triggering the auto-Crit?
Contrary to the ability name, the target creature does not have the surprised condition due to the Bugbear ability "Surprise Attack". As silly as it sounds, an ability only does what it says it does (IE titles don't matter).
If you surprise the creature and you attack them before they can take a turn (due to Initiative) then the damage will stack, but neither ability inherently cause the surprised condition, so they don't directly interact.
If you're not willing or able to to discuss in good faith, then don't be surprised if I don't respond, there are better things in life for me to do than humour you. This signature is that response.
Any creature you could Assassinate, you could also hit with Surprise Attack since a surprised creature will not have taken a turn in the combat yet. Rolling lower on initiative is not the same as being surprised however so no, you would not get the auto-crit from Assassinate by simple virtue of your target not having had their turn yet.
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.
So, I need a DM ruling...
Assassin Rogues get the 'Assassinate' skill which states:
Assassinate
Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.
Now, Bugbears have this Racial Trait:
Surprise Attack
If you hit a creature with an attack roll, the creature takes an extra 2d6 damage if it hasn’t taken a turn yet in the current combat.
Therefore, I ask, if you played a Bugbear Assassin Rogue, would this mean that if you attacked a creature who had yet to take their turn in combat yet, would that then count as a 'Surprise Attack' for the Rogue Assassinate Skill triggering the auto-Crit?
Go forth and argue, my children!!!
No.
Contrary to the ability name, the target creature does not have the surprised condition due to the Bugbear ability "Surprise Attack". As silly as it sounds, an ability only does what it says it does (IE titles don't matter).
If you surprise the creature and you attack them before they can take a turn (due to Initiative) then the damage will stack, but neither ability inherently cause the surprised condition, so they don't directly interact.
If you're not willing or able to to discuss in good faith, then don't be surprised if I don't respond, there are better things in life for me to do than humour you. This signature is that response.
Any creature you could Assassinate, you could also hit with Surprise Attack since a surprised creature will not have taken a turn in the combat yet. Rolling lower on initiative is not the same as being surprised however so no, you would not get the auto-crit from Assassinate by simple virtue of your target not having had their turn yet.
The rules for Surprise:
Birgit | Shifter | Sorcerer | Dragonlords
Shayone | Hobgoblin | Sorcerer | Netherdeep