"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. A member of a group can be surprised even if the others aren't."
Seems pretty clear to me, other than to say that nobody who is surprised can take a reaction until the turn ends, e.g. everyone in the initiative order has had a turn. If you are second in the initiative order out of six, then you cannot make use of a Reaction until all six creatures have had a turn.
This is entirely false. A turn refers to the actions of one character during the round. A round is over when all the combatant's respective turns are over. You are confusing turns and rounds.
So for clarity: You can take reaction after yourturn, even if that round isn't over, even if not everyone has gone yet.
The question I have is... when is a creature no longer considered "Surprised"? Like... Let's say that Assassin attacks Bandit and surprises him. Bandit rolls higher on Initiative, so technically gets the first turn of combat, but simply can't do anything with that turn. Is he still Surprised until the end of the round, or does hitting his Initiative end the Surprised condition?
This is a good question. Surprise rules suggest you simply either are surprised or not surprised for the encounter. By default, that only has effects on the first round, but... I suspect a RAW reading suggests you remain surprised for the entire combat encounter.
All we have is:
Any character or monster that doesn't notice a threat is surprised at the start of the encounter.
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. A member of a group can be surprised even if the other members aren't.
And this gives us no ending point for the condition other than some vague reference of the encounter. The effect of surprise, again, by default, only really impairs you on the first round of combat. It is 'effectively' over after that but not 'actually' not there. It is just a condition without an effect after round one.
Except, Assassinate... if you were to apply this ruling, gets, deadly OP.
So, RAI it is either over after your turn or after round one. But... RAW? I think it doesn't end until the encounter does.
SAC states more clearly that Surprise ends after their turn.
And both Assassinate effects work if you attack before others in the round by granting Advantage AND Auto-crit on those that you act before on the first round. You do NOT get Advantage nor Auto-Crit for anyone else.
When there is no surprise round, Assassin still gets Advantage on those he acts before in the first round.
This is balanced IMO, as long as your DM handles stealth and surprise positively.
Edit: creating a surprise round feels the most janky - as a DM, all this encourages is more and more “I take my bow out and attack the first bad guy around the corner!”, and countless “we all ready our attacks as soon as the door opens”, or the perennial “I take my dagger out super fast and attack the vampire we are talking to, so I get surprise?”
Creating a surprise round doesn't feel as janky to the people that actually played when the surprise round was a rule.
Maybe I should re-word it - creating a surprise round in the current rule set is janky. The only real difference is that creatures and PCs get a reaction if they roll higher on initiative. Trying to shoehorn a new process into it because “Assassins might not get a crit!” is janky.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
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.
I'm pretty sure this tells you how long surprise lasts...
Pretty sure it doesn't. It doesn't actually say it ends there. It just says that if you are surprised, there are some things you can't do in the first round of combat. Never actually says it ends on round one. Or even when on round one it would end.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
Yeah....its a horribly designed feature from PHB and honestly needs adjustment.
I would suggest the following:
Assassinate: You are used to getting the upper hand in a fight. When you take the Attack action on your turn you can use a BA to attempt one of the following:
A Deception Check (Charisma) vs the targets Insight Check (Wisdom) A Sleight of Hand Check (Dexterity) vs the targets Perception Check (Wisdom)
An Athletics Check vs the targets Athletics(STR) or Acrobatics(DEX) check
If you win the contest you do an additional 1d6 of sneak attack damage. This damage increases by 2d6 at (3d6) levels 5, (5d6) 11th, and (7d6) 17th. You can use this feature a number of times equal to your Proficiency Bonus. You regain all uses of this feature on a long rest.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
This is true..except for a couple of things, at least.
First, it's assumed that someone choosing the Rogue class and assassin subclass are going to have a good Dexterity score. Second, the game allows for things like the Alert feat which adds a bonus to your initiative roll.
So it's very attainable that by 4th level, a rogue could have +10 to their initiative roll, which is a huge advantage when determining order of actions in the game.
That, combined with other class and racial features, mean that even relatively low level assassins can use strategy and features to gain advantage/surprise.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
So win initiative if you wanna assassinate people? Why is that controversial or triggering for people? The slow lethargic assassin fails to get the jump on his intended target. Makes sense to me.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
So win initiative if you wanna assassinate people? Why is that controversial or triggering for people? The slow lethargic assassin fails to get the jump on his intended target. Makes sense to me.
Even if you max Dex, that's a +5 to Initiative on a 1-20 scale. You are only guaranteed to win ~25% of the time whether you get the jump on them or not (assuming they have a +0 to Dex). You could have expertise in stealth, never ever get noticed, and still lose out on the key feature of your subclass.
"I pop out of the shadows, the look of shock and terror on my targets face immediately melts away because he's not surprised anymore as I rolled a 2 on Initative, and he rolled a 10. My rapier slices him, but does absolutely no additional damage because his shock faded in the mere seconds it took for him to stand there and do nothing."
You're not making any sense whatsoever. If you lose the initiative roll you didn't get the drop on them.
Edit: You're far too fixated on stealth. Initiative is the measure of whether or not you can act before they act. That is where your assassin should be focused. Not stealth. Burglars and thiefs worry about that garbage. Assassins strike fast and first: That's initiative.
So let's rewrite that narrative:
"I pop out of the shadows, the look of shock and terror on my targets face melts away as I try to spring on him, but his reaction speed is simply faster than mine. (because he's not surprised anymore as I rolled a 2 on Initative, and he rolled a 10.) My rapier slices him, but does absolutely no additional damage because his shock faded in the critical first few seconds it took for me to fumble around and do nothing instead of attacking fast like my masters taught me. Maybe I won't botch the job next time."
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
This is true..except for a couple of things, at least.
First, it's assumed that someone choosing the Rogue class and assassin subclass are going to have a good Dexterity score. Second, the game allows for things like the Alert feat which adds a bonus to your initiative roll.
So it's very attainable that by 4th level, a rogue could have +10 to their initiative roll, which is a huge advantage when determining order of actions in the game.
That, combined with other class and racial features, mean that even relatively low level assassins can use strategy and features to gain advantage/surprise.
So let me see here you would need to:
Roll for stats
Roll an 18
Pick up the Alert feat at level 4 OR be v. human and pick it up at 1st level.
All this just to use your subclass effectively?
Honestly thats much more hassle than it should be.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
This is true..except for a couple of things, at least.
First, it's assumed that someone choosing the Rogue class and assassin subclass are going to have a good Dexterity score. Second, the game allows for things like the Alert feat which adds a bonus to your initiative roll.
So it's very attainable that by 4th level, a rogue could have +10 to their initiative roll, which is a huge advantage when determining order of actions in the game.
That, combined with other class and racial features, mean that even relatively low level assassins can use strategy and features to gain advantage/surprise.
So let me see here you would need to:
Roll for stats
Roll an 18
Pick up the Alert feat at level 4 OR be v. human and pick it up at 1st level.
All this just to use your subclass effectively?
Honestly thats much more hassle than it should be.
You could do all that, sure. Or, you could simply attack whatever enemy on round 1 rolled lower initiative than you. Seems almost guaranteed to happen most the time.
Edit: I mean. "boo hoo I can't always guarantee free critical hits every combat". Right there with you its such a bad feature.
You're not making any sense whatsoever. If you lose the initiative roll you didn't get the drop on them.
Edit: You're far too fixated on stealth. Initiative is the measure of whether or not you can act before they act. That is where your assassin should be focused. Not stealth. Burglars and thiefs worry about that garbage. Assassins strike fast and first: That's initiative.
So let's rewrite that narrative:
"I pop out of the shadows, the look of shock and terror on my targets face melts away as I try to spring on him, but his reaction speed is simply faster than mine. (because he's not surprised anymore as I rolled a 2 on Initative, and he rolled a 10.) My rapier slices him, but does absolutely no additional damage because his shock faded in the critical first few seconds it took for me to fumble around and do nothing instead of attacking fast like my masters taught me. Maybe I won't botch the job next time."
I mean, it is kinda impossible to focus on initiative outside of getting the Alert feat (which many DMs ban because it is often considered OP). Let's say that you choose to shoot from the shadows so the enemy has no idea you are there AT ALL. Let's say you even have the Alert feat and max Dex, getting you a +10 to initiative. Then you roll a 1. Your target has a ~50% chance of not being surprised by you even though he doesn't know you're there. And then you have to roll your attack ON TOP OF initiative. You have advantage, sure, but that's still no guarantee of success.
And the AR didn't fumble around and do nothing on his first turn, that was the target. But somehow, he still is no longer surprised. And an AR is pretty much made for picking of individual targets, like slowly killing guards on a wall. So if you only have one target, then you can't just pick someone with a lower initiative than you. I agree that this should not be "guaranteed free crits every combat", but if you do all the steps to ASSASSINATE someone, then you should absolutely get to use your ASSASSIN Rogue abilities.
But I'm sure you have some sort of mystical control of your dice so that you can "focus on initiative".
Welcome to D&D. We roll dice to randomly determine outcomes here.
You want a way to unfailingly kill enemies on round one. That's a different game I think.
You're not making any sense whatsoever. If you lose the initiative roll you didn't get the drop on them.
Edit: You're far too fixated on stealth. Initiative is the measure of whether or not you can act before they act. That is where your assassin should be focused. Not stealth. Burglars and thiefs worry about that garbage. Assassins strike fast and first: That's initiative.
So let's rewrite that narrative:
"I pop out of the shadows, the look of shock and terror on my targets face melts away as I try to spring on him, but his reaction speed is simply faster than mine. (because he's not surprised anymore as I rolled a 2 on Initative, and he rolled a 10.) My rapier slices him, but does absolutely no additional damage because his shock faded in the critical first few seconds it took for me to fumble around and do nothing instead of attacking fast like my masters taught me. Maybe I won't botch the job next time."
I mean, it is kinda impossible to focus on initiative outside of getting the Alert feat (which many DMs ban because it is often considered OP). Let's say that you choose to shoot from the shadows so the enemy has no idea you are there AT ALL. Let's say you even have the Alert feat and max Dex, getting you a +10 to initiative. Then you roll a 1. Your target has a ~50% chance of not being surprised by you even though he doesn't know you're there. And then you have to roll your attack ON TOP OF initiative. You have advantage, sure, but that's still no guarantee of success.
And the AR didn't fumble around and do nothing on his first turn, that was the target. But somehow, he still is no longer surprised. And an AR is pretty much made for picking of individual targets, like slowly killing guards on a wall. So if you only have one target, then you can't just pick someone with a lower initiative than you. I agree that this should not be "guaranteed free crits every combat", but if you do all the steps to ASSASSINATE someone, then you should absolutely get to use your ASSASSIN Rogue abilities.
But I'm sure you have some sort of mystical control of your dice so that you can "focus on initiative".
Welcome to D&D. We roll dice to randomly determine outcomes here.
I think the point is that the subclass itself confers no benefit to getting the leg up on your target....which combined with the abysmal design of the Assassinate feature makes it even worse.
Welcome to D&D. We roll dice to randomly determine outcomes here.
I think the point is that the subclass itself confers no benefit to getting the leg up on your target....which combined with the abysmal design of the Assassinate feature makes it even worse.
You attack at advantage (ie sneak attack) plus automatically crit if you win initiative attacking from stealth. That's pretty significant.
Class features don't often allow for guaranteed critical hits. That's not really how D&D works, we roll dice to determine outcomes.
Increase odds? Yea, rerolls? sure. A bonus here or there? yeah ok.
Guaranteed critical hits every combat on round one just because? Naw.
You're asking for something crazy OP. Sorry, you need to reevaluate your expectations.
Win initiative and your attacks crit. That's already really fantastic.
The Assassin is waiting in an alley for her target, and he comes walking in right on schedule, she waits, and he passes on by. She pops out of the shadows and he stops, and starts looking around. She knows he has been alerted somehow. He doesn't know where she is yet, but something has gone wrong, so she fades back into the shadows and waits. He looks around, can't find her, and he moves on, she pops back out of the shadows again, and this time he doesn't stop, so she goes though with the attack and he screams as the dagger sinks into his back.
There you go. She gets to roll twice to see if she hits and take the best roll, and if she hits, she's got a crit.
The trick here is that a target who is surprised and doesn't have the initiative keeps moving. The only reason they would stop is because they have the initiative. The Assassin doesn't even need to re-roll their stealth check. The target doesn't know where they are, but they do have an excuse to roll an active check and that's a benefit to all sides really, it keeps people from invariably being Assassinated, so it is possible they could find that Assassin, but the Assassin can have Expertise in Stealth, while the other than a Rogue or Bard you have to have the Skill expert feat to have Expertise in Perception.
As for the Alert feat, the main thing it does is make you immune to Surprise. The bonus to Initiative is just a nice perk. It's kind of wasted on a Rogue unless they are really paranoid, which, I suppose an Assassin might well be. If they both have it, the higher dex of the Rogue cancels out the initiative bonus of the feat, so the Rogue is still more likely to win the initiative. You don't need to have surprise to get the drop on someone, you just need to have the initiative, so the Assassin at least gets Advantage when they attack, so long as they get the initiative, and the odds are stacked in their favor.
Welcome to D&D. We roll dice to randomly determine outcomes here.
I think the point is that the subclass itself confers no benefit to getting the leg up on your target....which combined with the abysmal design of the Assassinate feature makes it even worse.
You attack at advantage (ie sneak attack) plus automatically crit if you win initiative attacking from stealth. That's pretty significant.
Class features don't often allow for guaranteed critical hits. That's not really how D&D works, we roll dice to determine outcomes.
Increase odds? Yea, rerolls? sure. A bonus here or there? yeah ok.
Guaranteed critical hits every combat on round one just because? Naw.
You're asking for something crazy OP. Sorry, you need to reevaluate your expectations.
Win initiative and your attacks crit. That's already really fantastic.
It's not based on the infrequently of it and finicky nature of the ability.
I already posted what I think is a better ability that doesn't use crits or the silly surprise rules.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
Except that as soon as an attack is brought up, initiative is rolled. Even if the NPC/monster has no idea that there is an Assassin Rogue hiding in the bushes, they have an initiative order. This means that they can still roll higher initiative than the AR and completely nullify the surprise aspect of the AR, making them no better than any other Rogue.
Murdering a lone guard from the shadows does not have to require initiative. The combat rules are a tool to be used when it makes sense to do so. You use your car to get around, but you don't need it to cross the street.
If an assassin wants to sneak around murdering guards, their chance of failure already rests in their ability to stay undetected. Assuming the guards are just basic mooks that would die in one crit, just let the assassin be an assassin.
This is entirely false. A turn refers to the actions of one character during the round. A round is over when all the combatant's respective turns are over. You are confusing turns and rounds.
So for clarity: You can take reaction after your turn, even if that round isn't over, even if not everyone has gone yet.
I got quotes!
This is a good question. Surprise rules suggest you simply either are surprised or not surprised for the encounter. By default, that only has effects on the first round, but... I suspect a RAW reading suggests you remain surprised for the entire combat encounter.
All we have is:
And this gives us no ending point for the condition other than some vague reference of the encounter. The effect of surprise, again, by default, only really impairs you on the first round of combat. It is 'effectively' over after that but not 'actually' not there. It is just a condition without an effect after round one.
Except, Assassinate... if you were to apply this ruling, gets, deadly OP.
So, RAI it is either over after your turn or after round one. But... RAW? I think it doesn't end until the encounter does.
I got quotes!
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.
I'm pretty sure this tells you how long surprise lasts...
SAC states more clearly that Surprise ends after their turn.
And both Assassinate effects work if you attack before others in the round by granting Advantage AND Auto-crit on those that you act before on the first round. You do NOT get Advantage nor Auto-Crit for anyone else.
When there is no surprise round, Assassin still gets Advantage on those he acts before in the first round.
This is balanced IMO, as long as your DM handles stealth and surprise positively.
Edit: creating a surprise round feels the most janky - as a DM, all this encourages is more and more “I take my bow out and attack the first bad guy around the corner!”, and countless “we all ready our attacks as soon as the door opens”, or the perennial “I take my dagger out super fast and attack the vampire we are talking to, so I get surprise?”
Creating a surprise round doesn't feel as janky to the people that actually played when the surprise round was a rule.
Maybe I should re-word it - creating a surprise round in the current rule set is janky. The only real difference is that creatures and PCs get a reaction if they roll higher on initiative. Trying to shoehorn a new process into it because “Assassins might not get a crit!” is janky.
My own take on the Assassin Rogue's rules for critical hits/advantage is that the RAW/RAI both are meant to help create opportunities for those characters to plan out or at least strategize a "hit" on an NPC or monster. They're not meant to be particularly handy in normal/group combat, where getting surprise is often difficult.
If the assassin rogue is scouting well ahead of the party, whether in wilderness or in a dungeon, then stealth, hiding, and darkness all provide ample chances for the assassin to apply those class features...but they're likely not going to be within easy reach of the party for help for at least a round or two.
Pretty sure it doesn't. It doesn't actually say it ends there. It just says that if you are surprised, there are some things you can't do in the first round of combat. Never actually says it ends on round one. Or even when on round one it would end.
I got quotes!
Yeah....its a horribly designed feature from PHB and honestly needs adjustment.
I would suggest the following:
Assassinate: You are used to getting the upper hand in a fight. When you take the Attack action on your turn you can use a BA to attempt one of the following:
A Deception Check (Charisma) vs the targets Insight Check (Wisdom)
A Sleight of Hand Check (Dexterity) vs the targets Perception Check (Wisdom)
An Athletics Check vs the targets Athletics(STR) or Acrobatics(DEX) check
If you win the contest you do an additional 1d6 of sneak attack damage. This damage increases by 2d6 at (3d6) levels 5, (5d6) 11th, and (7d6) 17th.
You can use this feature a number of times equal to your Proficiency Bonus. You regain all uses of this feature on a long rest.
This is true..except for a couple of things, at least.
First, it's assumed that someone choosing the Rogue class and assassin subclass are going to have a good Dexterity score. Second, the game allows for things like the Alert feat which adds a bonus to your initiative roll.
So it's very attainable that by 4th level, a rogue could have +10 to their initiative roll, which is a huge advantage when determining order of actions in the game.
That, combined with other class and racial features, mean that even relatively low level assassins can use strategy and features to gain advantage/surprise.
So win initiative if you wanna assassinate people? Why is that controversial or triggering for people? The slow lethargic assassin fails to get the jump on his intended target. Makes sense to me.
I got quotes!
You're not making any sense whatsoever. If you lose the initiative roll you didn't get the drop on them.
Edit: You're far too fixated on stealth. Initiative is the measure of whether or not you can act before they act. That is where your assassin should be focused. Not stealth. Burglars and thiefs worry about that garbage. Assassins strike fast and first: That's initiative.
So let's rewrite that narrative:
"I pop out of the shadows, the look of shock and terror on my targets face melts away as I try to spring on him, but his reaction speed is simply faster than mine. (because he's not surprised anymore as I rolled a 2 on Initative, and he rolled a 10.) My rapier slices him, but does absolutely no additional damage because his shock faded in the critical first few seconds it took for me to fumble around and do nothing instead of attacking fast like my masters taught me. Maybe I won't botch the job next time."
I got quotes!
So let me see here you would need to:
All this just to use your subclass effectively?
Honestly thats much more hassle than it should be.
You could do all that, sure. Or, you could simply attack whatever enemy on round 1 rolled lower initiative than you. Seems almost guaranteed to happen most the time.
Edit: I mean. "boo hoo I can't always guarantee free critical hits every combat". Right there with you its such a bad feature.
I got quotes!
Welcome to D&D. We roll dice to randomly determine outcomes here.
You want a way to unfailingly kill enemies on round one. That's a different game I think.
I got quotes!
I think the point is that the subclass itself confers no benefit to getting the leg up on your target....which combined with the abysmal design of the Assassinate feature makes it even worse.
You attack at advantage (ie sneak attack) plus automatically crit if you win initiative attacking from stealth. That's pretty significant.
Class features don't often allow for guaranteed critical hits. That's not really how D&D works, we roll dice to determine outcomes.
Increase odds? Yea, rerolls? sure. A bonus here or there? yeah ok.
Guaranteed critical hits every combat on round one just because? Naw.
You're asking for something crazy OP. Sorry, you need to reevaluate your expectations.
Win initiative and your attacks crit. That's already really fantastic.
I got quotes!
The Assassin is waiting in an alley for her target, and he comes walking in right on schedule, she waits, and he passes on by. She pops out of the shadows and he stops, and starts looking around. She knows he has been alerted somehow. He doesn't know where she is yet, but something has gone wrong, so she fades back into the shadows and waits. He looks around, can't find her, and he moves on, she pops back out of the shadows again, and this time he doesn't stop, so she goes though with the attack and he screams as the dagger sinks into his back.
There you go. She gets to roll twice to see if she hits and take the best roll, and if she hits, she's got a crit.
The trick here is that a target who is surprised and doesn't have the initiative keeps moving. The only reason they would stop is because they have the initiative. The Assassin doesn't even need to re-roll their stealth check. The target doesn't know where they are, but they do have an excuse to roll an active check and that's a benefit to all sides really, it keeps people from invariably being Assassinated, so it is possible they could find that Assassin, but the Assassin can have Expertise in Stealth, while the other than a Rogue or Bard you have to have the Skill expert feat to have Expertise in Perception.
As for the Alert feat, the main thing it does is make you immune to Surprise. The bonus to Initiative is just a nice perk. It's kind of wasted on a Rogue unless they are really paranoid, which, I suppose an Assassin might well be. If they both have it, the higher dex of the Rogue cancels out the initiative bonus of the feat, so the Rogue is still more likely to win the initiative. You don't need to have surprise to get the drop on someone, you just need to have the initiative, so the Assassin at least gets Advantage when they attack, so long as they get the initiative, and the odds are stacked in their favor.
<Insert clever signature here>
It's not based on the infrequently of it and finicky nature of the ability.
I already posted what I think is a better ability that doesn't use crits or the silly surprise rules.
Murdering a lone guard from the shadows does not have to require initiative. The combat rules are a tool to be used when it makes sense to do so. You use your car to get around, but you don't need it to cross the street.
If an assassin wants to sneak around murdering guards, their chance of failure already rests in their ability to stay undetected. Assuming the guards are just basic mooks that would die in one crit, just let the assassin be an assassin.
My homebrew subclasses (full list here)
(Artificer) Swordmage | Glasswright | (Barbarian) Path of the Savage Embrace
(Bard) College of Dance | (Fighter) Warlord | Cannoneer
(Monk) Way of the Elements | (Ranger) Blade Dancer
(Rogue) DaggerMaster | Inquisitor | (Sorcerer) Riftwalker | Spellfist
(Warlock) The Swarm