Alert, Stealth, and Initiative

[Xetheral]

I have to say, this is entirely theoretical as far as I'm concerned. In 10 years DMing multiple games per week and hundreds, if not thousands of encounters, I've had these conditions (perfectly stealthy party, with only one person doing anything to start combat, and then losing initiative badly) come up exactly zero times

I'm sure there's a lot of variation from table to table! I would note, however, the conditions under which this type of issue can come up aren't quite that narrow. The context in which it originally showed up (repeatedly) at my table was a party very prone to talking to potential antagonists--they were great at defusing potential combats. One of the PCs, however, was intemperate and on multiple occasions lost patience and decided to attack. Unfortunately the character wasn't dex-focused, and it was a very large party, virtually ensuring that the character never went first. Other PCs would take their first action in "combat" to go over and rest their hand on the initiating character's shoulder or otherwise try to defuse the situation before they actually attacked anyone. The intemperate character, not one to openly defy an appeal from a teammate, would abide and not attack when their turn came up, and we'd drop out of initiative.

This wasn't satisfying for anyone. The player of the intemperate character was getting frustrated, and some of the other players thought it would be more fun if the game had more combat in general (even though in any particular instance they preferred a nonviolent option). There were multiple possible solutions, such as having the enemies react violently to the almost-attack from the intemperate character (which did happen on occasion), but rather than having me put my thumb on the scale via changing how I RP'd the NPCs, we decided to go for a mechanical fix: our houserule that if only one person wants to initaite combat, they go at the top of the initiative order. It worked great! Tense social scenes became even more tense, as combat now (realistically) hinged on whomever was the least patient rather than allowing potentially combat-negating actions to abort a nascent combat before it could start in the narrative.

Other examples where combat-initiating oddities can come up include:

• a designated PC sneaking up to and starting combat with a sleeping monster (how does the monster get over their surprise if they spend their first turn asleep?)
• combat initiated by casting a subtle spell with no material component (how much do unsurprisable characters get to know if they act before the spell, and what happens if the spell they're reacting to isn't or can't be cast when the initator's turn comes up?)
• someone hidden wants to ready a combat action with a trigger that doesn't come up on the first turn (what does everyone else do, just keep doing what they were doing, but now they're in initiative?)
• a hidden character, hoping to disrupt the spellcasting, wants to attack a spellcaster who is in the process of casting a spell with a casting time of more than 1 action (if the spellcaster goes first they are surprised and can't take the required action to cast the spell, thus losing it, making the hidden character's attack unnecessary?)

It's great that you haven't had to deal with these sorts of issues at your table. But they definitely come up at other tables regularly enough to make the topic one worth discussing.

[Aimeryan]

I think (but am not 100% sure) you are referring to this:

Nah, its about the narrative dissonance of having entities be surprised about something that has yet to occur, then getting over it before it occurs, then reacting and not suffering from surprise when the hidden attack finally comes. It is around post #89 (id 25911146).

[GooeyChewie]

Nah, its about the narrative dissonance of having entities be surprised about something that has yet to occur, then getting over it before it occurs, then reacting and not suffering from surprise when the hidden attack finally comes. It is around post #89 (id 25911146).

Oh, in that case I responded in the same post you just quoted. In 5e, creatures are not surprised, mechanically speaking, by individual actions. They are surprised when combat starts and they were unaware of the other side of combat (and did not have a feature that prevents surprise). It’s a state of being unprepared for combat, not a reaction to any particular unexpected thing happening. Losing surprise is simply getting your guard up. The guy who is always on high alert (Alert or other surprise-canceling features) had his guard up anyway, the guy who always notices things (passive perception beat hide check) put his guard up when he saw the baddies, and the guy who isn’t on alert and didn’t notice the baddies might get to pull off some sort of defense if their reactions are fast enough (high initiative).

[Morgaln]

Only Alert would stop advantage and sneak attack

Storm rune does literally nothing. Its worthless.

Except of course if you just follow the rules its really good and makes Rune Knights really good.

So back to my question - in what circumstances would you just use the surprise mechanics by the book? When would these abilities be actually worth having. Or is Stealth basically just a win button in these games?

Storm rune still allows you to act in the first round of combat and it still allows you to perform your react. That is not nothing and it is not worthless. Unless you are claiming the "you can't be surprised " part of Alert also does nothing and is worthless.

Also, getting to act first in the first round of combat instead of your normal initiative order is nowhere near a win button.

[tokek]

Storm rune still allows you to act in the first round of combat and it still allows you to perform your react. That is not nothing and it is not worthless. Unless you are claiming the "you can't be surprised " part of Alert also does nothing and is worthless.

Also, getting to act first in the first round of combat instead of your normal initiative order is nowhere near a win button.

Its literally free sneak attack with no counter if you make the stealth check. Totally bypassing a feature that is supposed to make the character immune to being subject to surprise attacks.

Its too powerful and you have crippled its counters.

House rules are 100% fine but if you declared that one in session zero I would either switch character concept to abuse the hell out of it or just walk away and find a better game.

[Morgaln]

Its literally free sneak attack with no counter if you make the stealth check. Totally bypassing a feature that is supposed to make the character immune to being subject to surprise attacks.

Its too powerful and you have crippled its counters.

House rules are 100% fine but if you declared that one in session zero I would either switch character concept to abuse the hell out of it or just walk away and find a better game.

How does it prevent sneak attack if the ambusher rolls the highest initiative in the first place?

[Theodoxus]

OK so why do really dislike these outside-init surprise variants?

Let me ask their proponents - if being hidden means that anti-surprise mechanics should not work then when will they work? The only given mechanic for surprise is successful stealth that means we would consider the attacker hidden. So in 100% of the cases where we follow the rules as laid out the attacker who might gain the benefit of surprise is effectively hidden and you then do not follow the remaining steps laid out i the rules because they are hidden.

In 100% of cases all of these abilities to be immune to surprise are ineffective and useless if you do not continue with the rest of the process and instead roll surprise attacks before you roll init.

So for those who want it to work this way - please explain what exactly you think Alert / Storm Rune / Weapon of Warning etc actually do in your game? If they don't work when the attacker rolled stealth when can they actually do anything?

I'm going to use my variant (first strike outside combat, misses out on first round), because, well, I've run it this way for years.

I've noted how Alert isn't screwed by the first attack. At worst, you're missing out on what, Dodge and/or Hide? So, completely ineffective outside of saving your own skin?
Rune/Warning: Same as Alert, only the benefactors don't get a bonus to initiative (so potentially less likely to get two turns between the assassins 1st and 2nd turns), and don't negate advantage, so outside of other potentialities, they could get sneak attacked (if the assassin is a Rogue of some flavor). In either case, they're still immune to Surprise and will be able to act in the first round (provided they survived the initial attack).

Not sure where the disconnect is though.

How does it prevent sneak attack if the ambusher rolls the highest initiative in the first place?

Alert, I'm assuming? It negates advantage. If somehow the ambusher managed to get an ally into your group, so you're within 5' of an enemy, the sneak would still trigger... but otherwise, not so much.

The other ways to avoid surprise apparently don't have that provision (I'm AFB, so I can't corroborate the veracity of the statement).

[Morgaln]

Alert, I'm assuming? It negates advantage. If somehow the ambusher managed to get an ally into your group, so you're within 5' of an enemy, the sneak would still trigger... but otherwise, not so much.

The other ways to avoid surprise apparently don't have that provision (I'm AFB, so I can't corroborate the veracity of the statement).

I was referring to storm rune; because that one never negates sneak attack, according to my reading. The sneak attack comes from the attacker being hidden, not from the attacked being surprised, so storm rune does nothing against that by either way of playing.

[tokek]

I'm going to use my variant (first strike outside combat, misses out on first round), because, well, I've run it this way for years.

I've noted how Alert isn't screwed by the first attack. At worst, you're missing out on what, Dodge and/or Hide? So, completely ineffective outside of saving your own skin?

You are missing out on having a chance of doing anything. What that is depends on the character, what items they have and so on. But none of that matters if the attack absolutely always happens before you can act with no dice roll saying so and no abilities that can possibly counter it.

Those abilities become ribbon abilities really.

Meanwhile high Stealth becomes super-powered to an insane degree. Free attack. Just make sure it delivers a solid de-buff or control effect and its a rapid win with basically no dice involved at all (because getting your stealth bonus higher than a typical passive perception is far from hard).

That's a hard pass from me. The rules as written work far better.

[GooeyChewie]

I've noted how Alert isn't screwed by the first attack. At worst, you're missing out on what, Dodge and/or Hide? So, completely ineffective outside of saving your own skin?

Saving your own skin can be a pretty big deal. Also, there are other options. In addition to Dodge and Hide, you could:

Run away (dash)
Cast an AoE spell and hope to get lucky
Cast a defensive spell or a concentration spell
Ready an action to attack after an enemy reveals itself before it has a chance to hide again
Move to a location you expect would be more favorable
Shove an ally into a position you feel would be more favorable
Make an active Perception check to locate the enemy
Quaff a potion
Bluff in the hopes of scaring the attackers off

Probably a whole lot more that’s not coming to mind right off.

[Theodoxus]

You are missing out on having a chance of doing anything. What that is depends on the character, what items they have and so on. But none of that matters if the attack absolutely always happens before you can act with no dice roll saying so and no abilities that can possibly counter it.

Those abilities become ribbon abilities really.

Meanwhile high Stealth becomes super-powered to an insane degree. Free attack. Just make sure it delivers a solid de-buff or control effect and its a rapid win with basically no dice involved at all (because getting your stealth bonus higher than a typical passive perception is far from hard).

That's a hard pass from me. The rules as written work far better.

Why does it need to be stealth (high or otherwise). You're in a packed market square. You spot your bounty on the far side and decide to get the drop on them. Your target is in mid-haggle with a merchant, but has Alert. You're saying, boogaty-boogaty-boo, magic! the feat should allow the target to 1) know you're about to attack him from across the quad, 2) be able to roll initiative and possibly beat you, and 3) if they do, be able to attack you instead (or run away or whatever). And 4) you think that's working far better? That's not ever remotely realistic. And is on par (if not better) than a 9th level spell.

Saving your own skin can be a pretty big deal. Also, there are other options. In addition to Dodge and Hide, you could:

Run away (dash)
Cast an AoE spell and hope to get lucky
Cast a defensive spell or a concentration spell
Ready an action to attack after an enemy reveals itself before it has a chance to hide again
Move to a location you expect would be more favorable
Shove an ally into a position you feel would be more favorable
Make an active Perception check to locate the enemy
Quaff a potion
Bluff in the hopes of scaring the attackers off

Probably a whole lot more that’s not coming to mind right off.

And outside a potential hit with an AOE or readying to maybe attack, none of those are better than watching the attack proceed, and then getting a round (or easily 2) to pound the snot out of the assailant. YMMV, and I respect wanting to play it RAW (or at least closer to the mess that is RAW), but IMX, the dozen or so players who've used my modification have never expressed a desire to move away from it. The fact that both of the most modern 5E CRPGs use the same method at least shows the idea works.

[crayonshinchuck]

Mens Rea is the worst possible reason to roll for initiative. While yes, it's easier in a game to determine intent, it makes it nigh impossible to have a clear cut dividing line between combat and not combat.

Bob: "I think about attacking the guard, so I'm calling for initiative."
Bill: "Wait, *I* was going to attack the guard, I'm calling for initiative!"
Guard 1: "Hey, I have Alert, so I know what these hooligans are thinking of, it's written on their face, so I'm calling for initiative!"

Occam's Razor needs to be liberally applied here. Or, and this is probably an unpopular opinion, go back to 3x style Surprise Rounds, and it's in every combat (just conveniently ignored if every one is or isn't surprised.



There is no such thing as a 'surprise round' in 5E. Maybe that's the issue with this weird argument that a 'surprise attack' can't initiate combat? But it's also why I don't adopt the 'combat initiator automatically goes first every round'. Sure, they started combat, which opens up the first round. But they roll for initiative too; they just get a drop and go first, for the first round. When their actual spot in initiative comes up in that first round, they can't take any additional actions, bonus or otherwise, nor move. They had that chance at the top of the 1st round. Subsequent rounds, they act on their actual initiative.

If their opening salvo is ruled to cause surprise, then the Alert folks get to take their actions, on their initiative, in that first round. This stops the precog aspect that isn't in the Alert feat, while not negating the benefit of Alert. (It also negates the advantage from a hidden attack, which is quite useful against potential assassination attempts; and the +5 bonus to init means they're probably getting 2 attacks (round 1 and round 2) on the initiator before the would be assassin gets to act again.)

The main problem with your Bill, Bob, and Guard Scenario, is that you for some reason think that the player character calls for initiative. Bob's player would signal their intent to attack to the DM, who would then call for initiative, and whatever Bill's player thought about doing without stating their intentions to the DM is entirely irrelevant. You are acting like initiative is a real thing that the characters understand in their world, while it is actually just a way of abstracting the situation to provide the best representation of how a scene might play out in the game.

As has been stated elsewhere, an attack doesn't happen instantaneously. Bob's character would start their action, but the Alert guard would possibly be able to do something before Bob's character acts, due to the heightened reaction ability provided by the feat. Just because for game reasons each character gets their distinct turns to act, the imagined reality is that everyone is constantly acting throughout a round, with certain characters being able to get their actions in before or after others.

[tokek]

And is on par (if not better) than a 9th level spell.

Its on a par with an uncommon magic item, or a 10th level artificer infusion, or a 7th level Fighter subclass feature. Where on Toril do you get the idea that this is somehow on a par with 9th level spells?

Ambush must be the most dominant and busted thing in the game for an ability that counters it to be considered that powerful. I have never played in a game like that and I rather hope I never do.

[GooeyChewie]

Why does it need to be stealth (high or otherwise). You're in a packed market square. You spot your bounty on the far side and decide to get the drop on them. Your target is in mid-haggle with a merchant, but has Alert. You're saying, boogaty-boogaty-boo, magic! the feat should allow the target to 1) know you're about to attack him from across the quad, 2) be able to roll initiative and possibly beat you, and 3) if they do, be able to attack you instead (or run away or whatever). And 4) you think that's working far better? That's not ever remotely realistic. And is on par (if not better) than a 9th level spell.

1) They took a feat for the express purpose of being alert to such attacks. The target does not necessarily know that I am the one who is going to attack or how I am going to attack, only that they need to keep their guard up and be ready for combat.
2) They roll initiative and could possibly beat my initiative regardless of the feat. Normally beating me in initiative only means the target could use a reaction.
3) The whole point of taking the feat is to avoid letting people get the drop on you, so yes they should have a chance to do something to avoid me getting the drop on them.
4) Yes, this does work better than telling players who took a feat that prevents surprise that they can still be caught by surprise.

And no, this is nowhere close to a 9th level spell in power.

And outside a potential hit with an AOE or readying to maybe attack, none of those are better than watching the attack proceed, and then getting a round (or easily 2) to pound the snot out of the assailant. YMMV, and I respect wanting to play it RAW (or at least closer to the mess that is RAW), but IMX, the dozen or so players who've used my modification have never expressed a desire to move away from it. The fact that both of the most modern 5E CRPGs use the same method at least shows the idea works.

It depends on a lot of circumstances. For example, if that attack could drop you to 0 hit points then pretty much anything I listed is better than getting knocked out. Or if the attacker has the ability to hide as a bonus action (which is common among enemies who want to ambush), I would much rather be able to take some defensive measure on my turn before they attack than to get to my turn and ready an attack only to realize it’ll be my turn again before that trigger comes.

Granted, moving the attacker’s turn to the start of the round for the first round isn’t as bad as giving them a whole free attack. But it also doesn’t really help anything. If everybody was surprised, then the attacker was going to get the first turn anyway with RAW surprise, and all you’ve done is made it to where characters who beat the attacker in initiative can’t use reactions when the attacker attacks. In the case of characters with surprise-prevention features, you’re basically telling them they can still be surprised, just not as surprised as others. And then in the event that some characters see the attacker prior to rolling initiative and others don’t, it just creates a mess. Do they still go to the start of the round? If so, why do they get the jump on characters who saw them? If not, what do you do with the characters who didn’t see them but rolled well on initiative?

[Keltest]

Why does it need to be stealth (high or otherwise). You're in a packed market square. You spot your bounty on the far side and decide to get the drop on them. Your target is in mid-haggle with a merchant, but has Alert. You're saying, boogaty-boogaty-boo, magic! the feat should allow the target to 1) know you're about to attack him from across the quad, 2) be able to roll initiative and possibly beat you, and 3) if they do, be able to attack you instead (or run away or whatever). And 4) you think that's working far better? That's not ever remotely realistic. And is on par (if not better) than a 9th level spell.

Who cares if it's realistic? Preternatural senses are as much a fantasy trope as elves, for example. Let fantastic characters be fantastic.

[greenstone]

I think a lot of confusion goes away if we don't consider intiative to be "the order that things happen" but instead "the order that things are resolved."

If a hidden figure attacks but the player (or GM) rolls low, that doesn't indicate that the target gets to act before the attack starts; it means that the target gets to react before the attack finishes. The attacker has already started, already done something, otherwise the GM would not have moved the game into turn-based mode. The player doesn't get to walk it back if they roll badly on initiative, because their character has already kicked the situation off.

In the case of attacking a target across a crowded marketplace, the target percieves someone on the other side of the market telegraphing purposeful action, perhaps moving quickly, drawing a weapon, focusing their attention, whatever. The target doesn't know if it affects them or not, just that something serious just started, something that requires a response right now.

We should also consider it from a monster vs character persepctive. Would a player be happy if a GM says to them, "Your character just got hit, take 45 points of damage."?
"But don't I get to react or defend or do anything?" Nope.
"Don't I get to roll initiative?" Nope.

Most players are going to respond, "That's not fair!"

[tokek]

We should also consider it from a monster vs character persepctive. Would a player be happy if a GM says to them, "Your character just got hit, take 45 points of damage."?
"But don't I get to react or defend or do anything?" Nope.
"Don't I get to roll initiative?" Nope.

Most players are going to respond, "That's not fair!"

Exactly this - and if they have built their character specifically around the fantasy of being alert to danger and not vulnerable to being surprised they are going to be justifiably upset with a DM who does that. If they roll the dice and lose the roll that's part of the game, if you take the dice out of their hands and disregard the abilities they wanted their character to have then as a DM I think you are straying towards writing a book more than running a game.

If a player invests in not being vulnerable to ambush then when you run an ambush that's their chance to shine, to feel awesome. Why would a DM systematically take that away from their players?

[Kane0]

And it's even worse if it's not just a chunk of damage but a save against a spell or effect that would just remove you from the fight, or a spell or effect that would just remove you from the fight without a save.

[Theodoxus]

1) They took a feat for the express purpose of being alert to such attacks. The target does not necessarily know that I am the one who is going to attack or how I am going to attack, only that they need to keep their guard up and be ready for combat.
2) They roll initiative and could possibly beat my initiative regardless of the feat. Normally beating me in initiative only means the target could use a reaction.
3) The whole point of taking the feat is to avoid letting people get the drop on you, so yes they should have a chance to do something to avoid me getting the drop on them.
4) Yes, this does work better than telling players who took a feat that prevents surprise that they can still be caught by surprise.

And no, this is nowhere close to a 9th level spell in power.

Making it precognitive is on par with Foresight. So yes, it is exactly as powerful as a 9th level spell. The only real difference between the feat and the spell is advantage on rolls for the character, and having more than one disadvantage for the attacker.

We should also consider it from a monster vs character persepctive. Would a player be happy if a GM says to them, "Your character just got hit, take 45 points of damage."?
"But don't I get to react or defend or do anything?" Nope.
"Don't I get to roll initiative?" Nope.

Most players are going to respond, "That's not fair!"

So don't run monsters that way? But as a DM, I don't scream out 'that's not fair!' when a player decides to go full Corbin Dallas on some bugbear looking fool. I say 'cool, roll to hit' and then roll initiative.

I personally don't run ambushes on my players. At least not purposefully.

[starwolf]

Initiator starts combat, going first, every one else roll initiative.
Initiator is top init+1.
Nothing fiddly or complex and solves the surprise/ambush scenario.

[tokek]

Making it precognitive is on par with Foresight. So yes, it is exactly as powerful as a 9th level spell. The only real difference between the feat and the spell is advantage on rolls for the character, and having more than one disadvantage for the attacker.

That rather hyperbolic.

Storm Rune is described as glimpsing the future and precognitive but nobody thinks its as powerful as Foresight spell. Its a 7th level fighter feature, yes it is precognitive - that's exactly what its rules call it but claiming that all precognitive powers must therefore be equal or better than 9th level spells makes no sense.

But nor should it be almost worthless in an ambush situation because its specifically supposed to be useful in that situation.

[Aimeryan]

That's a hard pass from me. The rules as written work far better.

Yeah, this is several pages and posts now that you still don't understand that neither are the rules as written, because they are literally not written. When the DM calls for the initiative roll is completely DM fiat. There is no RAW on this.

[Morgaln]

Let's compare two different ways of playing out the same situation:

Number 1:

GM: You're walking along the road. Roll perception.

Jill: 11
Jack: 7
John: 14

GM: Nope, none of those beat the stealth roll of 16. Roll for initiative

Jill: 19. Nice!
Jack: 10. That's 15 with Alert
John: Oh crap, 3
Gm *notes a 12 for the hidden attacker*

GM. Alright, Jill, you're first. But you're surprised, so you can't do anything
Jill: Surprised by what? What happened?
GM: Nothing yet, you're first in initiative.
Jill: But I am surprised=
GM: Yes
Jill: Okay, I do nothing in the face of the nothing that surprised me.
GM. Alright, your turn is over, you are no longer surprised.
Jill: So I have now processed the thing that hasn't happened yet and therefore am no longer suprised by nothing?
GM. Yes
Jill. If you say so...

GM: Jack, you're up. You're not surprised because you have the alert feat
Jack: Okay, great. What can I do? What's happening?
GM: Nothing yet, the thing that is happening is later in initiative
Jack: So I can't do anything, really? I guess I take a martial arts stance and ready an attack in case anyone comes near me.

GM: Fair enough. The hidden attacker can attack now. at initiative 12. He's shooting his crossbow at John, because he's still flat-footed.
John: That sucks. And I won't even be able to attack on my turn because I'm still surprised, right?
GM: Correct
Jack: So my attack is wasted because he doesn't move, I guess? But I could have moved and attacked them if Alert hadn't given me that +5 to initiative?
GM: Yup. Since John is surprised, he can't do anything. So onward to round two.

---

Number 2:

GM: You're walking along the road. Roll perception.

Jill: 11
Jack: 7
John: 14

GM: Nope, none of those beat the stealth roll of 16. The first thing you notice of a hidden attacker is a crossbow bolt flying towards *rolls die* Jack. Since you're surprised, you take...
Jack: Hold on, I've got the Alert feat, I can't be surprised.
GM: Right you are. So you're not flat-footed.
Jack. I've got the deflect arrwos feat, can I use that?
GM: You can, it will count as your reaction for the first combat round.
Jack. Neat, I'll do that.

GM: Now that the attacker has revealed themselves, you can see him as an indistinct shadow in the bushes. Roll initiative.
Jill: 19. Nice!
Jack: 10. That's 15 with Alert
John: Oh crap, 3
GM: The attacker has a 12, but his attack just now counts as his attack for the first round. So he'll not act again until round two.
GM: Jill, you're up, but you are surprised.
Jill: I guess it takes a moment for me to process what just flew past my face.

GM: Jack, your turn.
Jack: I raise my fist with the arrow I caught and snap it in half. Then I charge the butthole before he can shoot again.

---

I know which one of these I would prefer, which of these feels more fluid and natural. But everyone needs to decide that for themselves.

[NichG]

With regards to the comparison to Foresight, that's part of the reason why as written I'd have Alert effectively give 'Jedi danger sense', because that particular game mechanical idea of 'this character cannot be surprised' is itself a very powerful thing. It's also one of the signature transformative abilities in Exalted, for that matter. Not to mention various fantasy media outside of tabletop RPGs. Being immune to being surprised is a Big Deal.

So rather than 'a feat should not be as powerful as a 9th level spell', I'd instead say 'if you write a feat carrying the same text as a 9th level spell, you're saying as a designer that's the level of power you want that feat to have'. Running Foresight differently than Alert would, IMO, be weird because they have the same text describing what it is they do. If you don't want a feat to have that level of power, don't write a feat that gives blanket abstract immunity to 'being surprised' in the first place. I don't think there's anything wrong with having a system where the abstract ability 'immune to surprise' is simply not available to characters. Remove that line from Alert and call it done. Or rewrite the line to say 'if they would otherwise not receive an action during a surprise round due to being caught by surprise, the character may instead act at the end of the surprise round and then on their normal initiative on subsequent rounds'. Or explicitly write the initiative system differently.

To put it another way, if the OP had asked 'how do you run Foresight in this case?' versus 'how do you run Alert in this case?', would we be having the same debate?

[Kish]

I know which one of these I would prefer, which of these feels more fluid and natural. But everyone needs to decide that for themselves.

How about these three scenarios?

Scenario 1:
Sam: I sneak into the room.
GM: Your stealth roll is successful. No one knows you're there.
The three other PCs: We wait to hear Sam make his move to open the door and charge in.
GM *rolls dice*: None of the enemies hear you positioning yourselves outside the door.
Sam: I attack the hobgoblin leader!
GM: Everyone roll initiative....Okay, Sam rolled lower than all the other PCs, the hobgoblin leader, and half the hobgoblins. Kate, you can attack now if you want.
Kate: I already said I'm not.
GM: Luke?
Luke: Also already said I'm not.
GM: Sarah?
Sarah: Also already said I'm not.
GM: Okay, the hobgoblin leader is next. He sees no enemy so he readies his action.
Sam: Hang on, what?
GM: That's what everyone does when they don't have something in-combat to do. You're up, Sam.
Sam: I attack the hobgoblin leader.
GM: Okay, he's damaged but still standing. He takes his readied action and attacks Sam, doing slightly over half Sam's hit points in damage. Kate, you're up next.
Kate: I kick in the door and attack.
GM: You down that hobgoblin. Two others take their readied actions and move to take his place at the doorway and attack you. Luke?
Luke: I attack.
GM: You down another hobgoblin. Sarah?
Sarah: I attack.
GM: Missed. The other hobgoblins attack...Next round. The hobgoblin chief goes first, attacking Sam again. He again does slightly over half Sam's hit points in damage.
Sam: I'm dead.

-----------------------------------------------------------------------------------------
Scenario 2:
Sam: I sneak into the room.
GM: Your stealth roll is successful. No one knows you're there.
The three other PCs: We wait to hear Sam make his move to open the door and charge in.
GM *rolls dice*: None of the enemies hear you positioning yourselves outside the door.
Sam: I attack the hobgoblin leader!
GM: Okay, he's damaged but still standing. Everyone roll initiative. Okay, the hobgoblin leader acts first and attacks Sam back, doing slightly over half Sam's hit points in damage. Kate, you're up.
Kate: I kick in the door and attack.
GM: You down that hobgoblin. Two others take their readied actions and move to take his place at the doorway and attack you. Luke?
Luke: I attack.
GM: You down another hobgoblin. Sarah?
Sarah: I attack.
GM: Missed. Sam, you're up.
Sam: I five-foot over to...here *points at battle map*, out of hobgoblin reach, and drink a healing potion.
GM: Okay. The other hobgoblins attack...

-----------------------------------------------------------------------------------------
Scenario 3:
Sam: I sneak into the room.
GM: Your stealth roll is successful. No one knows you're there.
The three other PCs: We wait to hear Sam make his move to open the door and charge in.
GM *rolls dice*: None of the enemies hear you positioning yourselves outside the door.
Sam: I attack the hobgoblin leader!
GM: Okay, he's damaged but still standing. Everyone roll initiative. Okay, Sam, you rolled highest so you're up again.
Sam: I attack him again.
GM: Okay, he's down. Two other hobgoblins move next, they both attack you. Then it's you, Sarah.
Sarah: I kick open the door and attack!
GM: You down that hobgoblin.

Which, if any, of those scenarios presents an unacceptable situation? And if any do, why is it unacceptable?

[OvisCaedo]

It is... quite an interesting take to claim that "immune to surprised" is in any way the main benefit of the Foresight spell, and therefore indicative of the power of the Alert feat.

[rel]

Oh, no, not quite. I think in the overwhelming majority of situations, it's fine for Alert to just be a vague precognition/danger sense, and the "surprise" mechanic works fine with the opening attack being after initiative is rolled. I think the Assassin's ability specifically gets potentially screwed over by this, but maybe IT should just be better written.

Apologies, I've modified my original post to reflect this.

For completeness, I don't use the optional feat rules, so I didn't venture an opinion of my own. However I do have an initiative houserule which might be relevant;

'A surprised character cannot be at the top of the initiative. If after determining initiative, a surprised character is at the top of the queue, increase the initiative of the unsurprised character with the highest initiative until they are at the top of the queue.'

[Salmon343]

Wading into this discussion. I'll say that although it isn't explicit, in its natural language style the PHB is fairly clear on initiative for surprising attacks - it's governed by the combat rules. The book tells us to run combat via the combat rules, essentially.

The combat rules tell us the order of events:
1) Determine Surprise
2) Establish Positions
3) Roll Initiative
4) Take Turns
5) Begin the Next Round

So if you'd consider what you're running to be "combat" - and I feel like any encounter with an assassin or the like falls under that - then these rules govern how it works. Yep there's no explicit link of attack or damaging action = combat, but I feel like it's reasonably clear under a natural language interpretation.
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There are a few arguments on how silly it is to have initiative running when you haven't been attacked yet and are unaware of the attacker. But this is just a quirk of the combat system, and does not reasonably affect the outcome.

A surprised creature cannot take actions or move on their first turn, and cannot take reactions until after their first turn. Essentially, you lose your first turn.

Let's work with one enemy. You can either be surprised and win initiative, or surprised and lose it. If you win initiative, then you still cannot act on your first turn. However, you can react later in the round. This could be casting Shield if you're attacked, or Intercepting an attack against an adjacent ally. If you lose initiative, you still cannot act on your first turn, nor can you react until afterwards - which is after the enemy has attacked.

What's the difference? Well if you win initiative, you can react to changing circumstances - if you lose initiative, you can't. All this condition is telling us is that the initiative roll governs whether you are quick enough to react to a surprising attack, even if you were not aware enough to act fully. We're talking about reflexive action versus considered action. Reflexive is much faster and intuitive, hence being able to get that off before you can even mentally register the threat. I admit that the language is tricky - being surprised before the triggering event - but this is just a language problem. If you just call surprised a state of "unreadiness to the inciting event", then you can use the word "surprise" however you like but the rules stay the same.
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The Alert feat grants three benefits. You cannot be surprised while conscious, you have a permanent +5 to initiative, and unseen targets don't gain advantage against you. Amending the surprise rules nerfs the first two benefits.

Under the normal rules, an Alert character cannot be surprised - thus they always get a turn while others may be surprised, and never lose their reaction to surprise. Making a hidden attacker (don't want to use the word surprise in multiple contexts at once, blame natural language) automatically go first removes the chance of the Alert character going first and being able to make preparations. More subtly, it also removes the chance of them getting an additional attack compared to their colleagues. If an Alert character rolls below the inciting event and everyone else is surprised then we have: Attacker -> Alert -> Next Round. If not, we have Attacker -> Next Round. (Even if the Alert character goes first we have, Alert -> Attacker -> Next Round, versus Attacker -> Next Round. They've lost a turn.)

I see no conceptual issue in an Alert character not being surprised. Firstly, it can be considered supernatural. Job done. Dragons breathe fire, Alert characters have a sixth-sense. Or you can be creative with the tells. An Alert character notices a slight shift in movement as the assassin prepares their attack, or the subtle facial changes of the enchanter before they unleash their Subtle Spell. Always on edge, they pick up these tells as a prelude to violence.
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So what do we do if an Alert character wins the initiative roll? Well combat has still begun, but the inciting event hasn't gone yet. However, the inciting event has begun. Initiative just determines the order of events.

Consider two duelists facing one another, in a free-form battle system. Duelist A charges with his weapon, but Duelist B is quick enough and is able to parry - and get off a counter-attack. There is an element of simultaneity here that D&D can find hard to model. What we understand here is that attacks are not instantaneous - A must move then strike, giving B time to process this and parry.

Combat began when you decided that the assassin was going to strike. Under a precognitive Alert, this could be them steeling their resolve. Under a hyper competent Alert, this could be them shifting their stance as they prepare to leap from the bushes. The enchanter narrows his eyes as he casts his spell, the devil appears before the party then goes in to strike.

Additionally, consider how you're using turns and the initiative system. Under my devil example, I've not had them teleport in and strike on the same turn. They've teleported, then combat has begun. After all, its not a battle of two sides until the devil is actually there - and loosely speaking the turn system doesn't really exist until combat has begun (if you were considering a special bonus action teleport into movement and action strike).
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Edit contents
The initiative system does have its quirks. But don't mistake those for issues with surprise. Under normal initiative rules, you'll always have some turns you would've spent differently had your opponent acted first. And my players having turns sandwiched between monster actions and healing often led to them yo-yoing, never having the turn to fully heal themselves (I've learnt from that mistake - avoid the boss with incessant actions!)

I think the solution here isn't to chuck surprise out of the window, but just import the Delay action into 5e. Drop your initiative, either for the entire encounter or just the round. And I'd make that a meta action - you don't have to justify it as a player. This way, initiative becomes a measure of reflexes not just a sorting tool. An Alert character always gets their counterattack, and aren't punished by winning initiative. But if they do win initiative, then they can bolster defenses, or strike first.

Edit 2
Although this might not be as beneficial as you think - if you import Delay as normal (an encounter permanent change), then you still get no more attacks in between enemy attacks - you just shift the turn number it happened in.

Say we have enemy X and Alert character A. If X can only take 2 attacks before going down, then in a world with only A and X, if A wins initiative we have:

(Round 1) A (no attack) -> X
(Round 2) A -> X
(Round 3) A -> FINISH

If A loses initiative we have:
(Round 1) X -> A
(Round 2) X -> A -> FINISH

Although we have 1 fewer round, we have the same number of X actions, and A has a prep turn in round 1 if they win initiative. So winning initiative isn't as bad as it looks - it just gives you a prep turn. Delaying would still be important for general turn order manipulation, however.

[GooeyChewie]

Let's compare two different ways of playing out the same situation:

...

I know which one of these I would prefer, which of these feels more fluid and natural. But everyone needs to decide that for themselves.

The fluidity of the scenarios you presented was determined largely by how you presented Jill, Jack and John each time, as well as how you had the GM explain (or fail to explain) things, rather than by the mechanics involved. If the DM explained that surprise just means you were not prepared for combat and not a reaction to a specific event, and Jack took a more sensible readied action of throwing a dart instead of one which required the opponent to approach him, the first scenario would have been much more fluid. If Jack complained about the attacker getting to attack despite him not being surprised, and Jill complained about how they were still surprised even though the event that supposedly surprised them was over and done, then the second scenario would have seemed a lot less fluid.

[tokek]

How about these three scenarios?

Scenario 1:
Sam: I sneak into the room.
GM: Your stealth roll is successful. No one knows you're there.
The three other PCs: We wait to hear Sam make his move to open the door and charge in.
GM *rolls dice*: None of the enemies hear you positioning yourselves outside the door.
Sam: I attack the hobgoblin leader!
GM: Everyone roll initiative....Okay, Sam rolled lower than all the other PCs, the hobgoblin leader, and half the hobgoblins. Kate, you can attack now if you want.
Kate: I already said I'm not.
GM: Luke?
Luke: Also already said I'm not.
GM: Sarah?
Sarah: Also already said I'm not.
GM: Okay, the hobgoblin leader is next. He sees no enemy so he readies his action.
Sam: Hang on, what?
GM: That's what everyone does when they don't have something in-combat to do. You're up, Sam.
Sam: I attack the hobgoblin leader.
GM: Okay, he's damaged but still standing. He takes his readied action and attacks Sam, doing slightly over half Sam's hit points in damage. Kate, you're up next.
Kate: I kick in the door and attack.
GM: You down that hobgoblin. Two others take their readied actions and move to take his place at the doorway and attack you. Luke?
Luke: I attack.
GM: You down another hobgoblin. Sarah?
Sarah: I attack.
GM: Missed. The other hobgoblins attack...Next round. The hobgoblin chief goes first, attacking Sam again. He again does slightly over half Sam's hit points in damage.
Sam: I'm dead.

This goes wrong because the GM got it horribly wrong unless this is a unique Hobgoblin NPC that has a special anti-surprise feature.

When the hobgoblin turns come up they don't get an action because they are subject to the surprise rules. They miss their turn. All that happens is that after that they would have a reaction, but regular hobgoblins don't have a very meaningful reaction

Basically the GM didn't read the the rules or was house-ruling a unique set of hobgoblins that are immune to being surprised.

Also the other players should have been readying actions or buffing or doing something useful on their turns. But that's just a normal level of players making mistakes. The GM having hobgoblins take any action at all after leading the players to believe they have the advantage of surprise is basically just shocking GM behaviour.