A couple of comments regarding Surprise and Encounters.
SURPRISE: Basic elements from the SRD pg. 90.
1. "Try to be stealthy." Player must announce their intent to surprise.
2. "The GM compares the Dexterity(Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side." Specific rule mechanic.
3. "Any character or monster that doesn't notice a threat is surprised at the start of the encounter." General intent of the rule.
First comment: Being that general rule trumps specific rule, as a DM I would be interested to see other ways that the players conceal their presence from hostile creatures in ways that do not involve a Dexterity(Stealth) check.
Whisper Bard, Mantle of Darkness comes to mind (XGE pg 16.) Disguise kits too. Deception or Performance vs. Insight or Investigation surprise check? If a monster does not notice a threat due to disguise, magic, or special abilities, is the monster surprised?
ENCOUNTERS: Another important dynamic in this rule is when an Encounter actually begins as a precondition of Surprise rules. From a practical standpoint, it is more important to discern how an Encounter ends. It is easy to get into an encounter. How do we know when the encounter ends so that we can initiate again?
Also from the OGL, 90: "The order of turns is determined at the beginning of a combat encounter when everyone rolls initiative. Once everyone has taken a turn, the fight continues to the next round if neither side has defeated the other."
This seems like an easy answer. No ending or re-initiating the encounter until one side has all their members go unconscious. However, the nature of "defeat" is more complex and not clearly defined in the surrounding SRD text.
DMG pg. 81 has a different definition for the context of an Encounter. I will not copy the material due to Wizards' copyright, but look at the definition if you can.
Per the DMG, is it possible to break contact and re-engage in a way that a party could re-activate Surprise rules and all the associated bonuses? (i.e. Rogue Assassin)
Well, first of all, I'm going to presume you meant "specific trumps general" and not the "general rule trumps specific rule" that you said. If not, be aware in the future that specific rules always trump any general rules if they do come up.
Surprise is a condition that can be imposed on a group until their turn during the first round of combat after initiative is rolled. It is entirely up to the DM to determine whether or not a creature is surprised, and they certainly can base it on things other than a Stealth check vs a Perception check. This is likely the most common way, but there are many others.
I would probably rule that if one person is having a peaceful conversation with another, and then suddenly whips out a dagger to stab them, that the person getting attacked would be surprised. You'd still roll initiative as soon as a hostile action is performed, as per usual, but even if the person getting stabbed rolls a higher initiative they'll be Surprised and thus won't get to go during the first round, allowing the attacker to stab them.
A disguise kit could certainly allow it without a Stealth check as well. If you disguise yourself in the same garb as a group of cultists, move into their group (perhaps in this case with a Deception vs Perception check) and then suddenly attack someone, I'd rule that the cultists are surprised by this. While a contested Deception check would have happened in this case, no Stealth check would have.
As for starting and stopping combat; sure, why not? If a group surrenders and the other group accepts, combat would stop and initiative would end. Someone could then make another attack - a hostile action - and initiative would be rolled again for a new encounter. This could also be a way to gain surprise; maybe one side is tied up but manages to escape their bonds while their captor's backs are turned, and they attack them. In this case it might need a Stealth roll to sneak up on them, but still, an example of initiative being broken and then starting again shortly after with the same groups.
What's important to note about Surprise is that it's a condition. I and many others like to call the first round a "surprise round," because it is a condition that can only happen during the first round of combat, but it's a condition nonetheless. On top of this, if everyone on one side isn't surprised by everyone on the opposite side, then no-one is surprised. One botched Stealth check among the party or one exceptional Perception check among the enemies means no surprise whatsoever; this likely stems from speaking being a free action, and that they'd be able to call out a warning before anything happens. Thus, it's generally recommended for anyone who benefits greatly from Surprise (Rogue Assassins) to sneak off ahead of the party and engage in combat with the party catching up to join in shortly after.
On that note it's also important to note that the Surprise condition doesn't last the entire round; it only lasts until a Surprised creatures turn. The condition prevents them from taking any Actions or Movement on their turn, but once their turn comes up in the initiative order they are no longer Surprised. This is important, because before they lose the condition they can not make Attacks of Opportunity; after they lose it they can. Also, the Assassin subclass - and some monsters - have benefits against creatures that have the Surprise condition, so if an enemies turn comes up before the Assassins then they will not get those bonus'.
All in all, it's really just up to the DM to determine if a group is surprised or not. There could be plenty of reasons they would be, Stealth check or not, but all said it's a fairly ambiguous rule.
To me the idea of surprise is dependant on being attacked without even knowing there is an attacker.
The way surprise plays out by the rules, is that if you don't notice an attacker, you can't act the first round of combat. But if you do notice the attackers, you are able to react to them in the same round as the attack.
So in your example of them being disguised or friendly before attacking, you still notice the attack as it happens, the same way it would have worked if an attacker failed their stealth check. In this situation, I would give advantage to the surprise attack and/or to initiative, but no surprised conditions.
That's fair. I have a player who is an assassin and is very into disguises and stuff, playing Assassin's Creed/Hitman style, as well as one who's a Gloomstalker. I'm typically pretty loose with the rules of surprise and Stealth in general.
On top of this, if everyone on one side isn't surprised by everyone on the opposite side, then no-one is surprised.
Not so, according to the Players Handbook: "A member of a group can be surprised even if the other members aren't." Surprise is a condition applied individually to each character, NPC, or creature involved in the combat.
Yes I didn't word that quite right, what I mean is if an enemy isn't surprised by every single party member they aren't surprised.
For example, say the whole party tries to sneak up on a group of enemies. Let's say there's two different kinds of enemies in the group they're sneaking up on; one has a Passive Perception of 14 and one has a Passive Perception of 9. The party rolls Stealth Checks and get 19, 18, 15 and 10. The enemy that has a Passive Perception of 9 will be surprised, since every party members Stealth Check beat their PP; however, the enemy with a PP of 14 will not be surprised, even though 3 out of 4 party members beat their PP with their Stealth Check.
So, generally speaking, it's better to have your stealthier characters go ahead and try to get a drop on the enemies before the rest of the party catches up.
But Jaysburn, my question still somewhat remains: If the stealthier players get the drop on the enemies, instead of having the rest of the party catch up, what rules govern having the stealthier players sneak away, allowing the opportunity to re-initiate combat?
SRD/PHB says that one side has to be defeated, but DMG says "partial success" is an option too. Partial damage to enemies = partial success? Allow stealth rolls each turn as players sneak away at 1/2 movement ("slow pace"), pulling back to end combat and re-initiate?
I'd think once you initiate the combat the players could attempt to escape, but the enemies would be able to pursue (or even attempt to block escape) in initiative order. If the players somehow manage to get away to regroup with their allies, the enemies are going to be on high alert and probably calling reinforcements - no way would they get surprised a second time.
Well that depends. If you mean having them sneak away while the rest of the party continues fighting and then come in again to get the drop on them, then no, Surprise definitely wouldn't happen. Surprise can only happen on the first round of combat after initiative is rolled; if more people join in, they are added to the initiative roll, but no one is surprised by them even if they were hidden because they Stealthed their way in to attack. If they are hidden from an enemy in this instance, they would certainly have advantage on their attack roll, but the enemy would not be surprised because initiative is already under way.
It's a different story if everyone on one side of combat were to sneak away, though that would be difficult. Remember, in order to hide you have to be completely out of line of sight, and even then the creature(s) you're hiding from will still know where they last saw you before you took the hide action. Still, if everyone on one side of combat did manage to sneak away, then as there would no longer be any threat to them or combat going on, initiative would end. They could then circle back and attack again, and if they manage to Sneak up then could potentially Surprise the enemy.
Bottom line is really that Surprise can only happen during the first round after Initiative; if initiative ends, for any reason, there will be opportunity to Surprise again. But sneaking or even running in and out of combat to try to surprise over and over, even once, probably isn't a good tactic.
Maybe for one or two very stealthy characters, but not for a balanced party. As you ask, a stealthier player could maybe get away with this, but it would be a bit silly in my opinion and probably boring for the other players. There also wouldn't be anything stopping the bad guys from changing their tactics, setting up traps, spreading out to find other threats, whatever during the time that the sneaky character is trying to get away/come around form another angle. It's also important to note that generally Sneaking is against Passive Perception, but if enemies know there's a threat they're going to be using the Search action a lot and thus further attempts to Sneak up will be against the higher between Perception rolls (AKA Active Perception) and their Passive Perception; they'll have an easier time detecting a hidden character.
This kind of thing is sorta what Rogues, particularly Assassins, are made for. They can hide as a bonus action allowing them to use their Action to dash and move 60 feet while still being able to hide. You don't have to move at half speed to move whiled hidden, but moving at normal speed is detrimental to their ability to perceive things such as traps. The move at half speed thing is mainly for going long distances while moving stealthily/covering up your traces of passage.
There's been a couple instances in my game where the Assassin player has scouted ahead, found a group of enemies, ambushed the closest one for a Surprise Sneak Attack and then ran away to inform the rest of the party. Good way to whittle down an enemy or two.
Yes I didn't word that quite right, what I mean is if an enemy isn't surprised by every single party member they aren't surprised.
Surprise (PHB 189):
A member of a group can be surprised even if the other members aren’t.
Surprise can only happen on the first turn of combat per creature, after which the creature no longer has the Surprised condition.
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.
However, if you want to play that a third faction joining a fray late might cause the Surprised condition, that's perfectly fine at your table. Flanking maneuvers like that were common military tactics and can, indeed, be called surprise attacks. (A third faction joining combat would be starting their first round of combat even though the other combatants were previously engaged). I would offer that the already engaged combatants would have advantage on the new initiative rolls.
I think you're misinterpreting that. Any character or monster that doesn't notice a threat, as in any threat whatsoever. They noticed 3/4 of the threats, so they noticed a threat and thus are not surprised. The 4th could still attack that creature from Stealth and have Advantage on their attack roll because of that, since they weren't noticed, but the creature is alerted by the other three, meaning they're "ready for combat" and thus won't have the Surprised condition.
As far as a third party entering combat, it wouldn't be the first round of combat and thus RAW no one would have the surprised condition. Of course, you can do what you want at your table, but it would make very little sense in practice.
Surprise prevents you from taking Actions or Movement on your turn, so how would that work happening in the middle of combat? A third party shows up and suddenly anyone who doesn't notice them doesn't get to take their turn this round, even though they're in the middle of combat? Maybe if EVERYONE in the combat was surprised, but the odds of that are slim to none, so it just really wouldn't make sense. That kind of thing is why you're given Advantage when you attack while hidden from a creature; so sneaking up does still have an advantage, even if they're not necessarily surprised by it. Otherwise Surprise and attacking from Stealth would be combined into one thing.
I don't think you could give anyone already engaged in combat the Surprised condition, as it just doesn't make sense. The surprised condition prevents you from taking any action or movement on your turn, and I can't see why new people showing up to an already ongoing battle would do this as the combatants are all already engaged. It wouldn't make sense for anyone who didn't notice their approach to suddenly lose their turn, as anyone already engaged who isn't surprised could then just beat on them or whatever.
However, you could always give the benefits to any creatures that get them from attacking a surprised creature in this case, even though they're not actually surprised. Let that Assassin do their Assassinate critical hit, why not?
According to RAW you cannot give anyone the surprised condition after their first turn of combat, I'm not trying to argue that point. If anything, you would probably gain Advantage from the maneuver.
I like the idea of catching the opponents, or players, off guard and having them unable to respond (surprised) to a third group. Giving advantage on the Initiative rolls, for those already in combat, would grant them the benefit of already being in motion. Another option would be to give the third group disadvantage instead. This way, if they do roll really well, they could then be considered able to gain surprise, the initiative isn't changed for the previous combatants, and all you have to do is slip the new combatants onto the initiative table.
Again, just spit-balling an idea, not trying to argue RAW :)
Thanks for the interest, yall. You might imagine how this dynamic could be a game-changer if we stack a party with a paladin-assassin-whisper bard and halforc-assassin-volley ranger. Getting two sneaky characters out front, deal a mess of damage, break contact, fall back to the main group, set up another surprise. Holy criticals!
The final point I found about breaking contact is in the situation of Ending a Chase. (DMG, pg, 253.) Looks like escaping from your foes is resolved very much like initiating surprise to begin with. I am fairly confident that the "break-contact" dynamic to end an encounter can be accomplished by stealth RAW.
Right - but remember that D&D enemies don't just reset like video game enemies. After the first attack they know someone's there, and will be much harder, if not impossible, to surprise again.
Indeed, Surprise can only happen when a creature is unaware of a threat. You can still sneak up on them, but if you fight something and then run away, it's going to be a while before they're not on their guard (feeling threatened) again.
Yes I didn't word that quite right, what I mean is if an enemy isn't surprised by every single party member they aren't surprised.
That's not accurate either. Surprise is an effect that applies individually for every iteration of creature-pairs present: Player 1 & enemy 2, player 1 & enemy 2, player 2 & enemy 1, player 2 & enemy 2, etc. By RAW, each iteration is resolved independently, but the outcome (as it relates to an entire side) can be confusing at times.
Enemy 2 may spot player 1 & fail to spot player 2.
Enemy 2 is not aware of player 2.
Enemy 1 may spot both player 1 & player 2.
Enemy 1 is aware of both players.
What this means is that all enemies have noticed a source of danger, so their entire side is not "surprised" as combat begins. However, that does not mean that enemy 2 is automatically aware of player 2. They did not notice player 2, and--while they can take their entire 1st turn as normal--player 2 is hidden from them.
Even if enemy 1 shouts "Hey enemy 2! Look out! There's another player over there!", enemy 2 cannot be aware of player 2 until: player 2 reveals themselves through their actions, or enemy 2 spends an action to make an active perception check.
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You don't know what fear is until you've witnessed a drunk bird divebombing you while carrying a screaming Kobold throwing fire anywhere and everywhere.
I know reading the entirety of these threads is tiring, but I did say that. That's not surprise though, which was my point. That's just sneaking up on them; they won't have the Surprise condition for the first round of combat, but the player(s) that beat their Passive Perception will, indeed, still be hidden from them.
Hello, first post here:
A couple of comments regarding Surprise and Encounters.
SURPRISE: Basic elements from the SRD pg. 90.
1. "Try to be stealthy." Player must announce their intent to surprise.
2. "The GM compares the Dexterity(Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side." Specific rule mechanic.
3. "Any character or monster that doesn't notice a threat is surprised at the start of the encounter." General intent of the rule.
First comment: Being that general rule trumps specific rule, as a DM I would be interested to see other ways that the players conceal their presence from hostile creatures in ways that do not involve a Dexterity(Stealth) check.
Whisper Bard, Mantle of Darkness comes to mind (XGE pg 16.) Disguise kits too. Deception or Performance vs. Insight or Investigation surprise check? If a monster does not notice a threat due to disguise, magic, or special abilities, is the monster surprised?
ENCOUNTERS: Another important dynamic in this rule is when an Encounter actually begins as a precondition of Surprise rules. From a practical standpoint, it is more important to discern how an Encounter ends. It is easy to get into an encounter. How do we know when the encounter ends so that we can initiate again?
Also from the OGL, 90: "The order of turns is determined at the beginning of a combat encounter when everyone rolls initiative. Once everyone has taken a turn, the fight continues to the next round if neither side has defeated the other."
This seems like an easy answer. No ending or re-initiating the encounter until one side has all their members go unconscious. However, the nature of "defeat" is more complex and not clearly defined in the surrounding SRD text.
DMG pg. 81 has a different definition for the context of an Encounter. I will not copy the material due to Wizards' copyright, but look at the definition if you can.
Per the DMG, is it possible to break contact and re-engage in a way that a party could re-activate Surprise rules and all the associated bonuses? (i.e. Rogue Assassin)
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Well, first of all, I'm going to presume you meant "specific trumps general" and not the "general rule trumps specific rule" that you said. If not, be aware in the future that specific rules always trump any general rules if they do come up.
Surprise is a condition that can be imposed on a group until their turn during the first round of combat after initiative is rolled. It is entirely up to the DM to determine whether or not a creature is surprised, and they certainly can base it on things other than a Stealth check vs a Perception check. This is likely the most common way, but there are many others.
I would probably rule that if one person is having a peaceful conversation with another, and then suddenly whips out a dagger to stab them, that the person getting attacked would be surprised. You'd still roll initiative as soon as a hostile action is performed, as per usual, but even if the person getting stabbed rolls a higher initiative they'll be Surprised and thus won't get to go during the first round, allowing the attacker to stab them.
A disguise kit could certainly allow it without a Stealth check as well. If you disguise yourself in the same garb as a group of cultists, move into their group (perhaps in this case with a Deception vs Perception check) and then suddenly attack someone, I'd rule that the cultists are surprised by this. While a contested Deception check would have happened in this case, no Stealth check would have.
As for starting and stopping combat; sure, why not? If a group surrenders and the other group accepts, combat would stop and initiative would end. Someone could then make another attack - a hostile action - and initiative would be rolled again for a new encounter. This could also be a way to gain surprise; maybe one side is tied up but manages to escape their bonds while their captor's backs are turned, and they attack them. In this case it might need a Stealth roll to sneak up on them, but still, an example of initiative being broken and then starting again shortly after with the same groups.
What's important to note about Surprise is that it's a condition. I and many others like to call the first round a "surprise round," because it is a condition that can only happen during the first round of combat, but it's a condition nonetheless.
On top of this, if everyone on one side isn't surprised by everyone on the opposite side, then no-one is surprised. One botched Stealth check among the party or one exceptional Perception check among the enemies means no surprise whatsoever; this likely stems from speaking being a free action, and that they'd be able to call out a warning before anything happens. Thus, it's generally recommended for anyone who benefits greatly from Surprise (Rogue Assassins) to sneak off ahead of the party and engage in combat with the party catching up to join in shortly after.
On that note it's also important to note that the Surprise condition doesn't last the entire round; it only lasts until a Surprised creatures turn. The condition prevents them from taking any Actions or Movement on their turn, but once their turn comes up in the initiative order they are no longer Surprised. This is important, because before they lose the condition they can not make Attacks of Opportunity; after they lose it they can. Also, the Assassin subclass - and some monsters - have benefits against creatures that have the Surprise condition, so if an enemies turn comes up before the Assassins then they will not get those bonus'.
All in all, it's really just up to the DM to determine if a group is surprised or not. There could be plenty of reasons they would be, Stealth check or not, but all said it's a fairly ambiguous rule.
To me the idea of surprise is dependant on being attacked without even knowing there is an attacker.
The way surprise plays out by the rules, is that if you don't notice an attacker, you can't act the first round of combat. But if you do notice the attackers, you are able to react to them in the same round as the attack.
So in your example of them being disguised or friendly before attacking, you still notice the attack as it happens, the same way it would have worked if an attacker failed their stealth check. In this situation, I would give advantage to the surprise attack and/or to initiative, but no surprised conditions.
That's fair. I have a player who is an assassin and is very into disguises and stuff, playing Assassin's Creed/Hitman style, as well as one who's a Gloomstalker. I'm typically pretty loose with the rules of surprise and Stealth in general.
Specific trumps general. Understood, thank you much!
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Not so, according to the Players Handbook: "A member of a group can be surprised even if the other members aren't." Surprise is a condition applied individually to each character, NPC, or creature involved in the combat.
Yes I didn't word that quite right, what I mean is if an enemy isn't surprised by every single party member they aren't surprised.
For example, say the whole party tries to sneak up on a group of enemies. Let's say there's two different kinds of enemies in the group they're sneaking up on; one has a Passive Perception of 14 and one has a Passive Perception of 9. The party rolls Stealth Checks and get 19, 18, 15 and 10.
The enemy that has a Passive Perception of 9 will be surprised, since every party members Stealth Check beat their PP; however, the enemy with a PP of 14 will not be surprised, even though 3 out of 4 party members beat their PP with their Stealth Check.
So, generally speaking, it's better to have your stealthier characters go ahead and try to get a drop on the enemies before the rest of the party catches up.
But Jaysburn, my question still somewhat remains: If the stealthier players get the drop on the enemies, instead of having the rest of the party catch up, what rules govern having the stealthier players sneak away, allowing the opportunity to re-initiate combat?
SRD/PHB says that one side has to be defeated, but DMG says "partial success" is an option too. Partial damage to enemies = partial success? Allow stealth rolls each turn as players sneak away at 1/2 movement ("slow pace"), pulling back to end combat and re-initiate?
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I'd think once you initiate the combat the players could attempt to escape, but the enemies would be able to pursue (or even attempt to block escape) in initiative order. If the players somehow manage to get away to regroup with their allies, the enemies are going to be on high alert and probably calling reinforcements - no way would they get surprised a second time.
Well that depends. If you mean having them sneak away while the rest of the party continues fighting and then come in again to get the drop on them, then no, Surprise definitely wouldn't happen. Surprise can only happen on the first round of combat after initiative is rolled; if more people join in, they are added to the initiative roll, but no one is surprised by them even if they were hidden because they Stealthed their way in to attack. If they are hidden from an enemy in this instance, they would certainly have advantage on their attack roll, but the enemy would not be surprised because initiative is already under way.
It's a different story if everyone on one side of combat were to sneak away, though that would be difficult. Remember, in order to hide you have to be completely out of line of sight, and even then the creature(s) you're hiding from will still know where they last saw you before you took the hide action. Still, if everyone on one side of combat did manage to sneak away, then as there would no longer be any threat to them or combat going on, initiative would end. They could then circle back and attack again, and if they manage to Sneak up then could potentially Surprise the enemy.
Bottom line is really that Surprise can only happen during the first round after Initiative; if initiative ends, for any reason, there will be opportunity to Surprise again. But sneaking or even running in and out of combat to try to surprise over and over, even once, probably isn't a good tactic.
Maybe for one or two very stealthy characters, but not for a balanced party. As you ask, a stealthier player could maybe get away with this, but it would be a bit silly in my opinion and probably boring for the other players. There also wouldn't be anything stopping the bad guys from changing their tactics, setting up traps, spreading out to find other threats, whatever during the time that the sneaky character is trying to get away/come around form another angle. It's also important to note that generally Sneaking is against Passive Perception, but if enemies know there's a threat they're going to be using the Search action a lot and thus further attempts to Sneak up will be against the higher between Perception rolls (AKA Active Perception) and their Passive Perception; they'll have an easier time detecting a hidden character.
This kind of thing is sorta what Rogues, particularly Assassins, are made for. They can hide as a bonus action allowing them to use their Action to dash and move 60 feet while still being able to hide. You don't have to move at half speed to move whiled hidden, but moving at normal speed is detrimental to their ability to perceive things such as traps. The move at half speed thing is mainly for going long distances while moving stealthily/covering up your traces of passage.
There's been a couple instances in my game where the Assassin player has scouted ahead, found a group of enemies, ambushed the closest one for a Surprise Sneak Attack and then ran away to inform the rest of the party. Good way to whittle down an enemy or two.
Surprise (PHB 189):
Surprise can only happen on the first turn of combat per creature, after which the creature no longer has the Surprised condition.
However, if you want to play that a third faction joining a fray late might cause the Surprised condition, that's perfectly fine at your table. Flanking maneuvers like that were common military tactics and can, indeed, be called surprise attacks. (A third faction joining combat would be starting their first round of combat even though the other combatants were previously engaged). I would offer that the already engaged combatants would have advantage on the new initiative rolls.
I think you're misinterpreting that. Any character or monster that doesn't notice a threat, as in any threat whatsoever. They noticed 3/4 of the threats, so they noticed a threat and thus are not surprised. The 4th could still attack that creature from Stealth and have Advantage on their attack roll because of that, since they weren't noticed, but the creature is alerted by the other three, meaning they're "ready for combat" and thus won't have the Surprised condition.
As far as a third party entering combat, it wouldn't be the first round of combat and thus RAW no one would have the surprised condition. Of course, you can do what you want at your table, but it would make very little sense in practice.
Surprise prevents you from taking Actions or Movement on your turn, so how would that work happening in the middle of combat? A third party shows up and suddenly anyone who doesn't notice them doesn't get to take their turn this round, even though they're in the middle of combat? Maybe if EVERYONE in the combat was surprised, but the odds of that are slim to none, so it just really wouldn't make sense. That kind of thing is why you're given Advantage when you attack while hidden from a creature; so sneaking up does still have an advantage, even if they're not necessarily surprised by it. Otherwise Surprise and attacking from Stealth would be combined into one thing.
I updated the post, I skimmed past the last line of Surprise and missed it at first.
"A member of a group can be surprised even if the other members aren’t."
I don't think you could give anyone already engaged in combat the Surprised condition, as it just doesn't make sense. The surprised condition prevents you from taking any action or movement on your turn, and I can't see why new people showing up to an already ongoing battle would do this as the combatants are all already engaged. It wouldn't make sense for anyone who didn't notice their approach to suddenly lose their turn, as anyone already engaged who isn't surprised could then just beat on them or whatever.
However, you could always give the benefits to any creatures that get them from attacking a surprised creature in this case, even though they're not actually surprised. Let that Assassin do their Assassinate critical hit, why not?
According to RAW you cannot give anyone the surprised condition after their first turn of combat, I'm not trying to argue that point. If anything, you would probably gain Advantage from the maneuver.
I like the idea of catching the opponents, or players, off guard and having them unable to respond (surprised) to a third group. Giving advantage on the Initiative rolls, for those already in combat, would grant them the benefit of already being in motion. Another option would be to give the third group disadvantage instead. This way, if they do roll really well, they could then be considered able to gain surprise, the initiative isn't changed for the previous combatants, and all you have to do is slip the new combatants onto the initiative table.
Again, just spit-balling an idea, not trying to argue RAW :)
Thanks for the interest, yall. You might imagine how this dynamic could be a game-changer if we stack a party with a paladin-assassin-whisper bard and halforc-assassin-volley ranger. Getting two sneaky characters out front, deal a mess of damage, break contact, fall back to the main group, set up another surprise. Holy criticals!
The final point I found about breaking contact is in the situation of Ending a Chase. (DMG, pg, 253.) Looks like escaping from your foes is resolved very much like initiating surprise to begin with. I am fairly confident that the "break-contact" dynamic to end an encounter can be accomplished by stealth RAW.
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https://forum.rpg.net/index.php?threads/serf2sove-5eogl.851074/
Right - but remember that D&D enemies don't just reset like video game enemies. After the first attack they know someone's there, and will be much harder, if not impossible, to surprise again.
Indeed, Surprise can only happen when a creature is unaware of a threat. You can still sneak up on them, but if you fight something and then run away, it's going to be a while before they're not on their guard (feeling threatened) again.
That's not accurate either. Surprise is an effect that applies individually for every iteration of creature-pairs present: Player 1 & enemy 2, player 1 & enemy 2, player 2 & enemy 1, player 2 & enemy 2, etc. By RAW, each iteration is resolved independently, but the outcome (as it relates to an entire side) can be confusing at times.
What this means is that all enemies have noticed a source of danger, so their entire side is not "surprised" as combat begins. However, that does not mean that enemy 2 is automatically aware of player 2. They did not notice player 2, and--while they can take their entire 1st turn as normal--player 2 is hidden from them.
Even if enemy 1 shouts "Hey enemy 2! Look out! There's another player over there!", enemy 2 cannot be aware of player 2 until: player 2 reveals themselves through their actions, or enemy 2 spends an action to make an active perception check.
You don't know what fear is until you've witnessed a drunk bird divebombing you while carrying a screaming Kobold throwing fire anywhere and everywhere.
I know reading the entirety of these threads is tiring, but I did say that. That's not surprise though, which was my point. That's just sneaking up on them; they won't have the Surprise condition for the first round of combat, but the player(s) that beat their Passive Perception will, indeed, still be hidden from them.