I'm trying to find out if a particular surprise attack & assassination loop would work out:
It is the rogue turn. He surprise attacks with 2 daggers at the same time. Does he get a surprise attack with both?
Assuming the rogue got a surprise attack with both daggers, do both trigger 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.
In case both trigger assassinate, would that be 2 critical hits? Would both critical hits each trigger Great Weapon Master?
Great Weapon Master
You've learned to put the weight of a weapon to your advantage, letting its momentum empower your strikes. You gain the following benefits:
- On your turn, when you score a critical hit with a melee weapon or reduce a creature to 0 hit points with one, you can make one melee weapon attack as a bonus action.
- Before you make a melee attack with a heavy weapon that you are proficient with, you can choose to take a -5 penalty to the attack roll. If the attack hits, you add 10 to the attack's damage."
At this moment, would the NPC still be surprised? If so, could both attacks earned from Great Weapon Master trigger Assassinate? If yes, can I loop like this?
If not, can this skulker rogue do the following: in a lightly obscured place, try to hide in plain sight. If the mobs are still considered surprised this turn (are they?), and the rogue has actions left, could he assassinate again and return to step 3?