What does Assassinate mean by "surprised", and can it be used multiple times?

Question

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)

Answer 1

From a very legalistic reading of the rules, you can use assassinate only once per encounter. Using it requires the opponents be surprised; they are only unaware of their opponents once in a fight; and stealth doesn't grant surprise status.

In effect, think of it like this: a surprised opponent is one that is entirely unprepared for being in a fight right this instant. When you attack an unsurprised opponent from hiding, they are already expecting attacks, so they are less vulnerable then when surprised but more vulnerable than when they can see you specifically.

It might actually be more and less complicated than that

However, that is a fairly conservative legalistic reading. It requires reading the description of surprise as ungenerously as possible—which, in general, is the safest way to read a rule when you're a player. Better to be right that you don't get goodies, than expect goodies and be wrong, yes?

That said, D&D Next is going to be weird for any player from the last decade and a half of D&D editions, because it has the explicit goal of reclaiming the heritage of AD&D and earlier editions that 3e left behind. And a major part of that heritage (for good or ill) is those editions' interpretability. Unlike 4e and (mostly) 3.x, the rules were only hard-and-fast where the rules were unambiguous, and where they were ambiguous the DM was expected to decide what worked best for their home game. When something was unclear in the rules, sometimes there was an official answer, but as often there wasn't.

This was considered a feature by the designers, especially in the original edition of D&D and in the Basic line. This was slightly less the case in AD&D because it was also meant to be the "tournament edition" of the game, but it never shook that heritage and it has interpretability very deeply ingrained into its structure and how the rules are explained.

Arguably, 3e didn't shake that heritage completely either. 3.5e got closer, but still has a few lacunae that drive people to distraction. 4e was the attempt to refine it to perfection and eliminate even the possibility of lacunae... and WotC didn't like the customer rebellion that edition caused. Hence Next, and why it is going "backwards" in many ways.

It's debatable whether Next is going "backwards" in regards to interpretability specifically, but as I hope I've shown, it's a distinct possibility that the rules for surprise and stealth are every-so-slightly unclear on purpose.

So what?

Well, so what? If the rules are unclear, then making the most conservative, power-limiting interpretation is correct, right?

Power problems might not actually be problems

Well, no, not exactly. Next is designed to have a much flatter power curve than any prior edition from Wizards of the Coast. A neat thing about a flattened power curve is that it makes the "sweet spot" of most-enjoyable levels much wider, which is a large part of why they wanted it. But also, as anyone can tell you who has experience with non-WotC D&D editions, a very flat power curve also means that character power is less variable and, often, a more-powerful character doesn't have the ability to travel far enough "upslope" on the power curve from the rest of the group; if the power curve is flat enough, or the character's advantage is unoptimal enough, they simply don't cross the threshold of problematic power difference.

So that's a neat feature. It was taken for granted by AD&D DMs and players, and it gave those groups much more flexibility and power to create interesting adventures and mixes of PCs without running into balance problems or putting constraints on story and adventure design. It was only in the 3e era that "power disparity" entered the lexicon of D&D players.

With Next's flatter power curve, it's entirely possible that power disparity problems are only in our habits learned from 3/4e, and aren't applicable to Next.

Surprise and stealth

So if Next doesn't have the kind of power-imbalance problems that we're used to having to squash, our habit of reading the rules as conservatively as possible may not apply. It wasn't necessary in pre-3e D&Ds, and maybe it won't be necessary with Next.

And if interpretability is a deliberate design feature of Next, then there may actually not be an official answer.

Combine these two possibilities, and you have an interesting result: it might not matter which way you read this rule. And if it might not matter, then different DMs might run this differently in their games, with some allowing Stealth to be used to hide your presence, and that counting for triggering "presence" condition necessary for surprise and assassination criticals.

This is often how AD&D DMs ran thieves' backstab ability. Given how much Next is attempting to recapitulate AD&D and earlier editions, and given how these rules around surprise and stealth look suspiciously similar to those earlier editions' rules for surprise and stealth, and given how the power curve of Next has been brought back into line with the power curves of AD&D and BD&D... I would not be surprised at all if the answer to this question was: Ask your DM.

Answer 2

Surprised only happens once...

In previous editions (3rd and 4th) surprised meant the party had succeeded in stealth enough to sneak up on enemies and ambush them. Mechanically this meant they got a "surprise round": a free round of happening prior to initiative. While surprised is not really defined in D&DNext I feel its safe to rely on this tradition as it spans multiple previous D&D editions. None of the scenarios you've given would be Surprised.

However, stealth and surprise are not synonymous. Your rogue's ability to stealth in combat may make him harder to hit and grant him a damage bonus but once combat kicks off enemies can no longer be surprised. I feel the fact that this is especially true because you gain access to this at level 3. Being able to crit every other round (as if in scenario 1a stealth gave you surprise) at level 3 would basically break the game.

Answer 3

I hope this will be an addendum to help clarify things for the rogues, especially with the mix of assassinate and sneak attack.

Surprised - this refers to the first turn in combat (page 189). A surprised creature is one that lose their first turn, or the longer explanation from the rulebook -- "can't move or take an action on [their] first turn of the combat, and [..] can't take a reaction until that turn ends."

Unseen attack - This is "when creatures can't see you, you have advantage on attack rolls against it." (page 195)

For an assassin archetype rogue, you have two abilities around this.

Sneak attack (page 96)

• 1d6/turn when you have advantage, or
• another unit within 5 ft of your target

Assassinate (page 97)

• Advantage on attack rolls on any creature that hasn't taken a turn in combat yet. and
• [A]ny hit you score against a creature that is surprised is a critical hit.

It is important to note that without assassinate, players do not get advantage when they surprise their enemy. In fact, it's the surprised creatures that lose their first round.

Below I'll present a few scenarios.

Let's call unseen attack advantage (a1) and assassinate advantage (a2) Let's call sneak attack damage (d1), and surprise crit (d2).

• Surprise and unseen - a1, a2, d1, d2
• Surprise and seen - a2, d1, d2
• No surprise, they haven't taken their turn, seen - a2, d1
• No surprise, they haven't taken their turn, unseen - a1, a2, d1
• No surprise, they took their turn, seen - nothing
• No surprise, they took their turn, unseen - a1, d1

For multiple advantages and disadvantages, you cancel them out one by one. The result is whether you have advantage or not. So if you have 1 advantage, and 1 disadvantage. "If circumstances cause a roll to have both advantage and disadvantage, you are considered to have neither of them." (page 173) Your attack is without advantage and you do not apply sneak attack damage.

173

To summarize and simplify, if you have advantage, you get the sneak attack damage. If the attacked creature was surprised, you attack does critical damage.

Answer 4

Note that it says, "unaware of their opponents’ approach or presence", plural, not "unaware of the attacker's approach or presence" singular.

Quite aside from any context in this or previous versions of D&D, this gives every appearance of an authorial intent that you're either surprised or you aren't, according to whether you're aware that there are opponents present. Hence you cannot be surprised by only one member from a group of opponents and unsurprised by the others, even if the one member has been up a tree so far.

That's a tragedy for anyone who likes the idea of assassinating someone out of a tree who's already engaged by (or just distracted by) goons, as you can in Assassin's Creed games for example. Still, that's not what "Assassinate" is designed to do.

I totally agree with SevenSidedDie, though, that if you want to evaluate surprise as a relationship between two particular characters (rather than the state of one character walking merrily along oblivious to danger, or being wary but missing the approaching opponents), then you get a plausible backstab rule. It's then for the DM (with your input) to decide what scenarios of hiding result in someone being unaware of your presence, as opposed to merely unaware of your precise location. That's just not the surprise mechanism actually described for use in the first round of combat encounters.