I need some elaboration on what is covered by "surprised". The Assassin Rogue’s special feature “Assassinate” states:
…In addition, if you (...) hit a creature that is surprised, you score a critical
The book says this about Surprise (pg 15 in “How to Play”), emphasis mine:
Creatures that were unaware of their opponents’ approach or presence are surprised.
The book says this about Stealth (pg 10-11 in “How to Play”):
Benefit of Being Hidden
You have advantage on the attack roll when you attack a creature from which you are hidden. Making an attack reveals your position, however.
My question is:
In relation to the Rogue's Assassinate special ability, is "surprised" ONLY referencing the original initiative order, or are there times when he may be granted this ability multiple times in a single combat encounter?
This may come into question in a number of scenarios:
Scenario 1 (Stealth): Combat is initiated, rogue goes first, benefits from “Assassin ability” then moves/hides (he gets a 3rd action remember) from everyone (for simplicity sake let’s say his stealth beats everyone’s perception esp since most rolls are +10(+Dex +Expertise +Proficiency)). Now the rest of the party & enemies go through their turns. Top of the initiative for 2nd round; Rogue attacks out of his hiding spot where nobody could see him, are they “surprised” by this attack?
Scenario 1a (Stealth): As a slight twist to the above (assuming the answer above is “not surprised”) would the following change this “condition”? After the rogue hid from everyone and before his next attack he continues sneaking to a completely different position and actually attacks from a spot 10’ away from where everyone last saw him go (ie, he dove into the brush and attacked from behind a tree 10’ away). Top of the 2nd round of Initiative, would the enemies now be surprised by the rogue’s attack that they didn’t see coming to begin with but is now originating from a different direction entirely?
Scenario 2 (3rd party entering combat in later rounds): PCs are engaged in combat with another group. A 3rd party exits an underground cellar & seeing only the dwarf fighter & ½ orc barbarian enters combat immediately adjacent to his location. He has now officially entered into the initiative counter, however, he is still completely unaware of the rogue as he is behind another wall having just killed some other lackey before his arrival and is preparing to join his companions. Since, even though he is in combat, the new combatant is completely unaware of the rogues existence wouldn’t that make him “surprised” when the rogue “rounds the bend” and throws a dart in his neck/sticks him with rapier etc?
My DM & I are discussing what the writer's intent behind this special ability was. Like so many things, this seems to be ambiguous. It also isn't covered by the “specific overrules the generic” guideline, since it’s not specifically spelled out in the special ability but leaves it up to the reader/DM to determine. The DM is temporarily ruling that this only applies to opponents who have not yet acted in initiative until we can get a better idea of how we think the rule is supposed to be played out.
(Feel free to format for clarity, I've written this several times and I can't seem to get it right)