You've missed the point. There was some discussion of allowing hostile actions such as attacks or spells to be resolved outside of combat, before combat begins. If a DM ever chooses to run a situation that way (again, imo this should be avoided) AND he also declares that the subsequent combat begins with the surprise mechanic, then you can have the enemy acting 3 times in a row. This is not intended by the rules.
The problem with allowing spells and attack action before combat round starts is that it's not always equal, Some DM tend to allow this it more with monsters than player characters i find..
You can cast spells outside combat without problem. But if you're trying to do so with other creatures, combat is engaged and initiative is rolled to determine turn order.
Without this it's chaos race where people constantly attempt to act before init.
There was an argument between the player and the GM regarding the surprise mechanics.
Description of the situation: During the night watch, the wizard approaching enemies and began to wake up his companions. Meanwhile, the GM attacked the bonfire with a web spell and the mage took damage from the unraveling spiderweb. After that, we all rolled the dice to determine the order of movement. The GM started the round first by casting another spell.
Player: He believes that the heroes were prepared to attack, so the opponent should not attack twice in a row. GM: I consider this an additional surprise round within the rules.
Generally, I read a bit on reddit and it can be concluded that it shouldn't work like that in 5e, but yesterday I saw an identical situation in one of the campaigns on YT, so I lost my mind. The next session is on Saturday, so we would like to clarify this.
It is entirely possible for wizard to have two rounds of Actions before some of the PC's can act. It depends on the Init rolls.
Say the Wizard rolls a 19 on Init, while a player B who is sleeping, rolls a 17.
The process:
DM adjudicates who is Surprised (ALL the sleeping PC's).
Round 1 starts, Everyone rolls for Init, with rolls as above.
Wizard casts Web.
Player B's turn comes up, but due to the Surprised condition, can take no Action, AND was Incapacitated, due to being asleep.
Round 2 starts.
Wizard goes again, due to the 19 versus 17.
Player B then goes.
That is RAW. And frankly, if I was DM'ing, I would ensure that the PC's were Prone, not in Medium or heavier armour, and had only ONE Object Interaction in Round 2 and all subsequent rounds. Player B wants to pick up a quiver of Arrows and a Bow, or a Shield and Sword, that takes up Object Interactions in Rounds 2 and 3, assuming the PC is awakened and not webbed. Most DM's (and players) want to handwave that set of rules away.
I think you've missed where it was pointed out that the players were fully aware of the enemies' presence. Surprise shouldn't have applied here. Unseen attackers perhaps, but not surprise.
There was an argument between the player and the GM regarding the surprise mechanics.
Description of the situation: During the night watch, the wizard approaching enemies and began to wake up his companions. Meanwhile, the GM attacked the bonfire with a web spell and the mage took damage from the unraveling spiderweb. After that, we all rolled the dice to determine the order of movement. The GM started the round first by casting another spell.
Player: He believes that the heroes were prepared to attack, so the opponent should not attack twice in a row. GM: I consider this an additional surprise round within the rules.
Generally, I read a bit on reddit and it can be concluded that it shouldn't work like that in 5e, but yesterday I saw an identical situation in one of the campaigns on YT, so I lost my mind. The next session is on Saturday, so we would like to clarify this.
It is entirely possible for wizard to have two rounds of Actions before some of the PC's can act. It depends on the Init rolls.
Say the Wizard rolls a 19 on Init, while a player B who is sleeping, rolls a 17.
The process:
DM adjudicates who is Surprised (ALL the sleeping PC's).
Round 1 starts, Everyone rolls for Init, with rolls as above.
Wizard casts Web.
Player B's turn comes up, but due to the Surprised condition, can take no Action, AND was Incapacitated, due to being asleep.
Round 2 starts.
Wizard goes again, due to the 19 versus 17.
Player B then goes.
That is RAW. And frankly, if I was DM'ing, I would ensure that the PC's were Prone, not in Medium or heavier armour, and had only ONE Object Interaction in Round 2 and all subsequent rounds. Player B wants to pick up a quiver of Arrows and a Bow, or a Shield and Sword, that takes up Object Interactions in Rounds 2 and 3, assuming the PC is awakened and not webbed. Most DM's (and players) want to handwave that set of rules away.
I think you've missed where it was pointed out that the players were fully aware of the enemies' presence. Surprise shouldn't have applied here. Unseen attackers perhaps, but not surprise.
Pointed out by whom? The OP has not made a 2nd post to qualify the situation.
A sleeping PC is not aware of ANYTHING.
IF they were all awake, and IF enough time had elapsed for the awakened players to pick up their gear, and ready themselves for combat, then the OP should not have said "began to awaken". My statement is accurate for any sleeping PC.
Potentially fine on the point about "beginning" to wake up, but the second they're awake (and especially if being alerted to danger) surprise no longer applies to any woken individual. Second, the Web is clearly being used offensively (as tactics to slow the enemy are considered an offensive move in combat). That should be in the first round of combat, not before, and the wizard at the very least can't be considered surprised, so they'd get a move that same round.
he GM attacked the bonfire with a web spell and the mage took damage from the unraveling spiderweb.
Another DM houserules is that web are flammable but don't propagate to instantly burn the area, any 5-foot cube of webs exposed to fire burns away in 1 round, dealing 2d4 fire damage to any creature that starts its turn in the fire. So RAW for the Wizard character to take fire damage it would have needed to stand in the same space as the bonfire and start it's turn there, meaning after initiative is rolled and it's turn comes up.
The grammar of the OP isn't very good, but a lot of us are interpreting the initial setup differently than JustaFarmer. The Wizard mentioned early on is a PC who is on watch, not the NPC who is attacking. That Wizard "detects" approaching enemies and began to wake up his companions. (the word "detects" is completely missing -- this just appears to be an error while writing the post)
It is unclear what type of spellcaster the GM controls that casts the web spell. The web spell was fully resolved outside of combat by this GM.
The "mage" is the same Wizard from before -- the PC who was on watch.
but the second they're awake (and especially if being alerted to danger) surprise no longer applies to any woken individual.
Well, this goes back to the mechanics that we were discussing earlier. Should yelling to wake up and alert PCs of imminent danger automatically mean that those PCs cannot be surprised? Or do those PCs who just woke up still have to be able to spot an actual enemy in order to not be surprised? Suppose the sleeping PC wakes up inside of a tent -- he might have no way of seeing or hearing enemies from there and therefore would auto-fail perception and automatically be surprised. Or, maybe they still get to make the perception check based on hearing alone?
Anyway, it seems like we weren't all thinking of the original situation in the same way, but that doesn't matter too much -- the discussion should be about how we should generally run these types of encounters.
It is correct that a surprised creature might be subjected to their enemy acting on two turns in a row before being able to act. But, in my opinion we should never allow a hostile action before combat begins AND award surprise for effectively 3 turns in a row. Specific situations such as the Hex example -- I would have to think about that further.
And, while technically yes a DM is free to simply never start combat, the clear intent of the rules is to do so immediately as soon as either party wishes to initiate a hostile action, such as an attack or a offensive spellcast. Heck sometimes even a clearly preparory-for-combat buff is the right time to call for it.
This encounter should have been initiated when the mage noticed them and they noticed the mage noticed. Maybe right away, maybe as soon as he tried to wake someone. Either way, the mage is absolutely not surprised. Nor is anyone he wakes before initiative.
And the web should have been cast on that spellcasters first turn of combat. Whether people were surprised or not.
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I'm probably laughing.
It is apparently so hard to program Aberrant Mind and Clockwork Soul spell-swapping into dndbeyond they had to remake the game without it rather than implement it.
Going back to my example, if the GM's Wizard is the NPC attacker, and Mage is player B, who was asleep.
Yeah, as others mentioned, this just shows you're misunderstanding the situation. The player's wizard was on watch and noticed the approaching enemies. They started alerting the sleeping members before the Web was ever cast. Player B's character wasn't asleep at all, so the rest of the post simply doesn't apply to them.
Also, how do you run this situation when the PC on watch IS surprised? Do the sleeping PCs automatically wake up when combat begins? When the first noisy hostile action is resolved? Do they stay asleep until the PC on guard duty gets a chance to yell a warning on his turn? (As an aside, I am confident that even if surprised the PC on guard duty CAN yell a warning on his first turn -- surprise restricts actions and movement, but not "other activity" such as flourishes, brief communication and an item interaction such as drawing a sword) Obviously I would assume that even if they wake up they are surprised on Round 1 (and only Round 1, regardless of when they wake up).
If I was running this and the PC on watch IS surprised then they can't take actions or reactions on their first turn. Neither can anyone else in the camp since they are also surprised because they were asleep.
The character on watch could yell (assuming they haven't been silenced) which would likely wake up the entire camp but would not remove the surprise. (Surprise applies if the creature does not notice a threat at the start of combat - actions by other creatures can not remove surprise from other creatures in the combat - so yelling doesn't remove it - it does ensure that the sleeping PC wakes up though).
I would also rule that the sleeping PCs would also otherwise wake up assuming that there is anything happening that would wake them up. If a sorcerer subtly cast a sleep spell on the PC on watch then as long as the attackers don't accidentally wake anyone up (likely stealth vs passive perception at disadvantage as an ersatz for whatever awareness the character would have while sleeping) then they would all remain asleep.
Of course that is full of rulings where the DM has to adjudicate the specific circumstances but that is what the DM does.
RAW, there is no rule that says creatures automatically wake up in combat. The DM has to decide based on circumstances.
How about this? Suppose no watch is set and all are asleep. The monsters are NOT attempting to be stealthy. Do PCs wake up AND automatically notice threats before combat begins?
You aren’t surprised if even one of your foes fails to catch you unawares.
As part of other activities on your turn, you can communicate however you are able, through brief utterances and gestures, as you take your turn. Shouting to wake up sleeping party members and warn them of ambushers would be up to DM if allowed.
But if the PC on watch is surprised, would you make them wait until their turn in initiative before they can shout a warning?
That feels like the most obvious way to resolve it unless context gives you a good reason to do otherwise (can't think of any offhand), since speaking is listed under "Other Activity On Your Turn", suggesting it's only supposed to take place on your turn.
I've never played in any groups that enforce the idea that characters can only speak on their own turn as such, but I think it's fair to limit "substantial communication", i.e- anything that might affect combat rather than exclamations of pain/surprise/etc. So raising an alarm would be assumed to have taken place on the character's turn, either being resolved then, or only characters who take a turn afterwards get to respond to it (or test to see if they heard) etc.
Since being surprised only prevents you from moving or taking any type of action before the end of your first turn, you can still do anything that doesn't require movement or an action/bonus action/reaction, which would include speaking. I tend to view surprise personally as being caught unprepared, rather than frozen in panic; you were facing the wrong one way at the wrong moment, or you have your weapons nearby but are scrambling to pick them up etc., anything that would delay you enough that you're not actually ready to fight yet.
I also picture it like the classic movie trope of someone shouting out an alarm a moment before they're shot, if you get high enough in initiative you can get the warning off before you're brought down, while the enemy is hoping to get you before you can.
The actual value of setting a watch is very situational, and as much about positioning IMO; if you're keeping watch on a forest clearing then the obvious point at which for the DM to roll for keeping watch/surprise is right before the enemy emerges from the treeline (i.e- their last moments of being hidden from you, assuming your passive perception didn't spot them earlier). But the more distant that treeline is, the less able enemies are to bring you down before the alarm is raised, and the less likely to be taken out before you can get a proper turn. So the more you can do to control how close ambushers are able to get before combat begins, the better.
Again this is the benefit of spells like alarm and faithful hound, or just generally setting physical traps, or a tripwire with a bell etc., because these can be used to expand your detection area, give you additional or alternative ways to be alerted, fish for advantage on the checks, or push back the distance at which an ambush might begin etc. Not every group will actually take account of these kinds of things, but I think that's a shame as it's part of the fun of wilderness survival in the game IMO, i.e- building up your camp and securing it. I wouldn't run all travel like that or it could get tedious, but when players are in an especially dangerous area or such it can be fun to emphasise.
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The thing about “I shout to wake the party up” is that a single round of combat hypothetically represents a period of about 6 seconds. Now, I don’t know about all of you, but the first 6 seconds after I wake up, my brain is still on screensaver. If a party who is wide awake and proceeding down a path with weapons at the ready can still have members suffer the surprise condition from enemies suddenly striking from cover, there’s no reason a party who has just woken from sleep by someone shouting an alarm can’t.
Also, just to address the point about Web; even if it’s not anchored it still functions- you can layer it 5 ft deep on a flat surface as opposed to stringing it up.
"You're caught by surprise as you're awakened by shouting and suddenly find yourself entangled in a web on fire. Initiative." sounds a bit too rough start to me ;)
"You're caught by surprise as you're awakened by shouting and suddenly find yourself entangled in a web on fire. Initiative." sounds a bit too rough start to me ;)
Oh yes; all that before initiative is too much, but it’s honestly a fair play to roll initiative while surprised, and if the other guy rolls well enough first end up surrounded by webbing and then have the webbing catch fire before your second turn starts. Granted, I’d also say you can’t get Web into a tent because of LoS, so anyone not sleeping under the stars is spared that bit.
But if the PC on watch is surprised, would you make them wait until their turn in initiative before they can shout a warning?
I would say yes. Remember that a round of turns all happens within the same 6-second window, so any actions before their turn in initiative just happen faster than they can react.
How about this? Suppose no watch is set and all are asleep. The monsters are NOT attempting to be stealthy. Do PCs wake up AND automatically notice threats before combat begins?
Still no. Before combat begins, the sleeping creatures are unaware of their surroundings (per the Unconscious condition). I'd rule you need a noise as loud as a shout at least to alert the sleeping members.
The thing about “I shout to wake the party up” is that a single round of combat hypothetically represents a period of about 6 seconds. Now, I don’t know about all of you, but the first 6 seconds after I wake up, my brain is still on screensaver. If a party who is wide awake and proceeding down a path with weapons at the ready can still have members suffer the surprise condition from enemies suddenly striking from cover, there’s no reason a party who has just woken from sleep by someone shouting an alarm can’t.
I would operate under the assumption that it would be more akin to hearing a person screaming "Fire!" in the home. You're more likely to snap awake when adventuring than when someone just barges in and wakes you up at home.
But if the PC on watch is surprised, would you make them wait until their turn in initiative before they can shout a warning?
I would say yes. Remember that a round of turns all happens within the same 6-second window, so any actions before their turn in initiative just happen faster than they can react.
How about this? Suppose no watch is set and all are asleep. The monsters are NOT attempting to be stealthy. Do PCs wake up AND automatically notice threats before combat begins?
Still no. Before combat begins, the sleeping creatures are unaware of their surroundings (per the Unconscious condition). I'd rule you need a noise as loud as a shout at least to alert the sleeping members.
The thing about “I shout to wake the party up” is that a single round of combat hypothetically represents a period of about 6 seconds. Now, I don’t know about all of you, but the first 6 seconds after I wake up, my brain is still on screensaver. If a party who is wide awake and proceeding down a path with weapons at the ready can still have members suffer the surprise condition from enemies suddenly striking from cover, there’s no reason a party who has just woken from sleep by someone shouting an alarm can’t.
I would operate under the assumption that it would be more akin to hearing a person screaming "Fire!" in the home. You're more likely to snap awake when adventuring than when someone just barges in and wakes you up at home.
Regardless of the exact circumstance, it takes the brain several seconds to engage- aka one round. In point of fact, the Alert feat specifically states that you cannot be surprised unless you are unconscious, which seems to reinforce the idea that if initiative is rolled and you’re asleep, then you will have the surprised condition.
But if the PC on watch is surprised, would you make them wait until their turn in initiative before they can shout a warning?
I would say yes. Remember that a round of turns all happens within the same 6-second window, so any actions before their turn in initiative just happen faster than they can react.
How about this? Suppose no watch is set and all are asleep. The monsters are NOT attempting to be stealthy. Do PCs wake up AND automatically notice threats before combat begins?
Still no. Before combat begins, the sleeping creatures are unaware of their surroundings (per the Unconscious condition). I'd rule you need a noise as loud as a shout at least to alert the sleeping members.
The thing about “I shout to wake the party up” is that a single round of combat hypothetically represents a period of about 6 seconds. Now, I don’t know about all of you, but the first 6 seconds after I wake up, my brain is still on screensaver. If a party who is wide awake and proceeding down a path with weapons at the ready can still have members suffer the surprise condition from enemies suddenly striking from cover, there’s no reason a party who has just woken from sleep by someone shouting an alarm can’t.
I would operate under the assumption that it would be more akin to hearing a person screaming "Fire!" in the home. You're more likely to snap awake when adventuring than when someone just barges in and wakes you up at home.
Regardless of the exact circumstance, it takes the brain several seconds to engage- aka one round. In point of fact, the Alert condition specifically states that you cannot be surprised unless you are unconscious, which seems to reinforce the idea that if initiative is rolled and you’re asleep, then you will have the surprised condition.
Even so, the scenario we were given was that the person on watch noticed and had already begun alerting the party before anything was cast. Which would likely mean they were awake at the time of casting/encounter.
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You've missed the point. There was some discussion of allowing hostile actions such as attacks or spells to be resolved outside of combat, before combat begins. If a DM ever chooses to run a situation that way (again, imo this should be avoided) AND he also declares that the subsequent combat begins with the surprise mechanic, then you can have the enemy acting 3 times in a row. This is not intended by the rules.
The problem with allowing spells and attack action before combat round starts is that it's not always equal, Some DM tend to allow this it more with monsters than player characters i find..
You can cast spells outside combat without problem. But if you're trying to do so with other creatures, combat is engaged and initiative is rolled to determine turn order.
Without this it's chaos race where people constantly attempt to act before init.
I think you've missed where it was pointed out that the players were fully aware of the enemies' presence. Surprise shouldn't have applied here. Unseen attackers perhaps, but not surprise.
Potentially fine on the point about "beginning" to wake up, but the second they're awake (and especially if being alerted to danger) surprise no longer applies to any woken individual. Second, the Web is clearly being used offensively (as tactics to slow the enemy are considered an offensive move in combat). That should be in the first round of combat, not before, and the wizard at the very least can't be considered surprised, so they'd get a move that same round.
Another DM houserules is that web are flammable but don't propagate to instantly burn the area, any 5-foot cube of webs exposed to fire burns away in 1 round, dealing 2d4 fire damage to any creature that starts its turn in the fire. So RAW for the Wizard character to take fire damage it would have needed to stand in the same space as the bonfire and start it's turn there, meaning after initiative is rolled and it's turn comes up.
The grammar of the OP isn't very good, but a lot of us are interpreting the initial setup differently than JustaFarmer. The Wizard mentioned early on is a PC who is on watch, not the NPC who is attacking. That Wizard "detects" approaching enemies and began to wake up his companions. (the word "detects" is completely missing -- this just appears to be an error while writing the post)
It is unclear what type of spellcaster the GM controls that casts the web spell. The web spell was fully resolved outside of combat by this GM.
The "mage" is the same Wizard from before -- the PC who was on watch.
Well, this goes back to the mechanics that we were discussing earlier. Should yelling to wake up and alert PCs of imminent danger automatically mean that those PCs cannot be surprised? Or do those PCs who just woke up still have to be able to spot an actual enemy in order to not be surprised? Suppose the sleeping PC wakes up inside of a tent -- he might have no way of seeing or hearing enemies from there and therefore would auto-fail perception and automatically be surprised. Or, maybe they still get to make the perception check based on hearing alone?
Anyway, it seems like we weren't all thinking of the original situation in the same way, but that doesn't matter too much -- the discussion should be about how we should generally run these types of encounters.
It is correct that a surprised creature might be subjected to their enemy acting on two turns in a row before being able to act. But, in my opinion we should never allow a hostile action before combat begins AND award surprise for effectively 3 turns in a row. Specific situations such as the Hex example -- I would have to think about that further.
If you're aware of an enemy you're not surprised.
And, while technically yes a DM is free to simply never start combat, the clear intent of the rules is to do so immediately as soon as either party wishes to initiate a hostile action, such as an attack or a offensive spellcast. Heck sometimes even a clearly preparory-for-combat buff is the right time to call for it.
This encounter should have been initiated when the mage noticed them and they noticed the mage noticed. Maybe right away, maybe as soon as he tried to wake someone. Either way, the mage is absolutely not surprised. Nor is anyone he wakes before initiative.
And the web should have been cast on that spellcasters first turn of combat. Whether people were surprised or not.
I'm probably laughing.
It is apparently so hard to program Aberrant Mind and Clockwork Soul spell-swapping into dndbeyond they had to remake the game without it rather than implement it.
Yeah, as others mentioned, this just shows you're misunderstanding the situation. The player's wizard was on watch and noticed the approaching enemies. They started alerting the sleeping members before the Web was ever cast. Player B's character wasn't asleep at all, so the rest of the post simply doesn't apply to them.
If I was running this and the PC on watch IS surprised then they can't take actions or reactions on their first turn. Neither can anyone else in the camp since they are also surprised because they were asleep.
The character on watch could yell (assuming they haven't been silenced) which would likely wake up the entire camp but would not remove the surprise. (Surprise applies if the creature does not notice a threat at the start of combat - actions by other creatures can not remove surprise from other creatures in the combat - so yelling doesn't remove it - it does ensure that the sleeping PC wakes up though).
I would also rule that the sleeping PCs would also otherwise wake up assuming that there is anything happening that would wake them up. If a sorcerer subtly cast a sleep spell on the PC on watch then as long as the attackers don't accidentally wake anyone up (likely stealth vs passive perception at disadvantage as an ersatz for whatever awareness the character would have while sleeping) then they would all remain asleep.
Of course that is full of rulings where the DM has to adjudicate the specific circumstances but that is what the DM does.
RAW, there is no rule that says creatures automatically wake up in combat. The DM has to decide based on circumstances.
But if the PC on watch is surprised, would you make them wait until their turn in initiative before they can shout a warning?
How about this? Suppose no watch is set and all are asleep. The monsters are NOT attempting to be stealthy. Do PCs wake up AND automatically notice threats before combat begins?
You aren’t surprised if even one of your foes fails to catch you unawares.
As part of other activities on your turn, you can communicate however you are able, through brief utterances and gestures, as you take your turn. Shouting to wake up sleeping party members and warn them of ambushers would be up to DM if allowed.
That feels like the most obvious way to resolve it unless context gives you a good reason to do otherwise (can't think of any offhand), since speaking is listed under "Other Activity On Your Turn", suggesting it's only supposed to take place on your turn.
I've never played in any groups that enforce the idea that characters can only speak on their own turn as such, but I think it's fair to limit "substantial communication", i.e- anything that might affect combat rather than exclamations of pain/surprise/etc. So raising an alarm would be assumed to have taken place on the character's turn, either being resolved then, or only characters who take a turn afterwards get to respond to it (or test to see if they heard) etc.
Since being surprised only prevents you from moving or taking any type of action before the end of your first turn, you can still do anything that doesn't require movement or an action/bonus action/reaction, which would include speaking. I tend to view surprise personally as being caught unprepared, rather than frozen in panic; you were facing the wrong one way at the wrong moment, or you have your weapons nearby but are scrambling to pick them up etc., anything that would delay you enough that you're not actually ready to fight yet.
I also picture it like the classic movie trope of someone shouting out an alarm a moment before they're shot, if you get high enough in initiative you can get the warning off before you're brought down, while the enemy is hoping to get you before you can.
The actual value of setting a watch is very situational, and as much about positioning IMO; if you're keeping watch on a forest clearing then the obvious point at which for the DM to roll for keeping watch/surprise is right before the enemy emerges from the treeline (i.e- their last moments of being hidden from you, assuming your passive perception didn't spot them earlier). But the more distant that treeline is, the less able enemies are to bring you down before the alarm is raised, and the less likely to be taken out before you can get a proper turn. So the more you can do to control how close ambushers are able to get before combat begins, the better.
Again this is the benefit of spells like alarm and faithful hound, or just generally setting physical traps, or a tripwire with a bell etc., because these can be used to expand your detection area, give you additional or alternative ways to be alerted, fish for advantage on the checks, or push back the distance at which an ambush might begin etc. Not every group will actually take account of these kinds of things, but I think that's a shame as it's part of the fun of wilderness survival in the game IMO, i.e- building up your camp and securing it. I wouldn't run all travel like that or it could get tedious, but when players are in an especially dangerous area or such it can be fun to emphasise.
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The thing about “I shout to wake the party up” is that a single round of combat hypothetically represents a period of about 6 seconds. Now, I don’t know about all of you, but the first 6 seconds after I wake up, my brain is still on screensaver. If a party who is wide awake and proceeding down a path with weapons at the ready can still have members suffer the surprise condition from enemies suddenly striking from cover, there’s no reason a party who has just woken from sleep by someone shouting an alarm can’t.
Also, just to address the point about Web; even if it’s not anchored it still functions- you can layer it 5 ft deep on a flat surface as opposed to stringing it up.
"You're caught by surprise as you're awakened by shouting and suddenly find yourself entangled in a web on fire. Initiative." sounds a bit too rough start to me ;)
Oh yes; all that before initiative is too much, but it’s honestly a fair play to roll initiative while surprised, and if the other guy rolls well enough first end up surrounded by webbing and then have the webbing catch fire before your second turn starts. Granted, I’d also say you can’t get Web into a tent because of LoS, so anyone not sleeping under the stars is spared that bit.
I would say yes. Remember that a round of turns all happens within the same 6-second window, so any actions before their turn in initiative just happen faster than they can react.
Still no. Before combat begins, the sleeping creatures are unaware of their surroundings (per the Unconscious condition). I'd rule you need a noise as loud as a shout at least to alert the sleeping members.
I would operate under the assumption that it would be more akin to hearing a person screaming "Fire!" in the home. You're more likely to snap awake when adventuring than when someone just barges in and wakes you up at home.
Regardless of the exact circumstance, it takes the brain several seconds to engage- aka one round. In point of fact, the Alert feat specifically states that you cannot be surprised unless you are unconscious, which seems to reinforce the idea that if initiative is rolled and you’re asleep, then you will have the surprised condition.
Even so, the scenario we were given was that the person on watch noticed and had already begun alerting the party before anything was cast. Which would likely mean they were awake at the time of casting/encounter.