Surprise round question

Hriston

Dungeon Master of Middle-earth (He/him)
All you need to do to get events to be credible is to roll opposed Stealth/Perception checks to find out if the assassin did something to awaken the sleeper!

What would make sense is to find out whether or not the assassin did in fact make a commotion, or at least whether or not the target woke up, taking into account the Stealth skills of the assassin, the Perception skills of the sleeper, and luck.

I have two problems with your approach to finding out whether the sleeping target awakens before the start of combat.

First, sleeping creatures are unconscious. Specifically, they are unaware of their surroundings. This means their passive Perception is turned off. The latest Sage Advice covers this: http://dnd.wizards.com/articles/features/james-haeck-dd-writing. Jeremy Crawford states it explicitly at around 22:30. The sleeping creature's Perception couldn't possibly be a deciding factor in whether it wakes up or not.

Second, your willingness to engage the fortune mechanic with reference to the assassin's DEX (Stealth) check seems to assume that the task of sneaking up on a sleeping creature wouldn't be a very easy task, even for a trained assassin. IME, it's very easy to avoid the notice of a sleeping person if that's your goal. And even if you aren't trying to avoid notice and are instead trying to accomplish some task that makes a loud noise, the sleeping person still won't notice you until after s/he is first awakened by the sound. For example, if I come home from work late, and someone is asleep in an adjoining room, it's very easy for me to stay quiet and avoid awakening that person, but if I start doing the dishes because the kitchen was left a mess, it's quite possible that the noise I make will wake up the sleeper.

For fun, I thought it might be interesting to lay out the mechanical differences between our approaches. Your method results in four possible outcomes.

1. The assassin wins the DEX/WIS contest and initiative. S/he is unnoticed, and, when combat begins, the still-sleeping creature is surprised. The assassin attacks with advantage if within 5 feet of the prone creature, and any hit is critical. The sleeping creature awakens upon taking damage and remains surprised until the end of its turn.

2. The assassin wins the DEX/WIS contest, but the sleeping creature wins initiative. The assassin is unnoticed, and the sleeping creature is surprised at the start of combat, but, although it remains asleep, it ceases to be surprised at the end of its turn but can't take reactions because it's still asleep. The assassin must be within 5 feet of the prone, sleeping creature not only to gain advantage on the attack but to score a critical hit as well. Upon taking damage, the creature awakens.

3. The sleeping creature wins the DEX/WIS contest, but the assassin wins initiative. The sleeping creature notices the assassin and wakes up before combat starts. The assassin attacks the still-prone creature with advantage if within 5 feet. On its turn, the creature can stand up from prone and/or move and act.

4. The sleeping creature wins the DEX/WIS contest and initiative. It notices the assassin and wakes up before combat starts. On its turn, it can stand up from prone and/or move and act normally. The assassin's attack may have advantage if the assassin remains unseen, but otherwise the assassin attacks as normal.

My method, on the other hand, produces two outcomes that are possible.

1. The assassin wins initiative. S/he is unnoticed, and when combat begins, the creature is awakened and surprised. The assassin attacks with advantage if within 5 feet of the prone creature, and any hit is critical. The creature remains surprised until the end of its turn. (Note that this is mechanically identical to your outcome 1., the only difference being that I have the sleeping creature awaken to be surprised, which is narrative rather than mechanical.)

2. The sleeping creature wins initiative. The assassin is unnoticed, and when combat begins, the creature is awakened and surprised. The creature stops being surprised at the end of its turn and can take reactions on the assassin's turn. The assassin attacks with advantage if within 5 feet of the prone creature but doesn't auto-crit. (This is similar to your outcome 2., except that the creature gets to take reactions by virtue of having won initiative.)

The main difference in outcomes I see here doesn't stem from the timing of the creature's awakening. It stems from the fact that in my approach the sleeping creature is automatically surprised due to being unaware of its surroundings.

Was the sleeper going to wake up to empty his bladder anyway? Does a drunk smash a bottle outside and waken the sleeper just at the wrong moment?

Roll that opposed check and find out!

How does skill in Perception make someone more likely to have a full bladder? Do low WIS/low Perception characters in your games frequently wet themselves?

How does an assassin's botched DEX (Stealth) check cause a drunk to smash a bottle outside? Or is it the sleeping creature's high Perception that allows it to be roused by the constant smashing of bottles that exists in your game-worlds?
 

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Arial Black

Adventurer
I have two problems with your approach to finding out whether the sleeping target awakens before the start of combat.

First, sleeping creatures are unconscious. Specifically, they are unaware of their surroundings. This means their passive Perception is turned off. The latest Sage Advice covers this: http://dnd.wizards.com/articles/features/james-haeck-dd-writing. Jeremy Crawford states it explicitly at around 22:30. The sleeping creature's Perception couldn't possibly be a deciding factor in whether it wakes up or not.

You and I both agree that, while unconscious creatures are 'unaware', their senses continue to function. Conceptually, being 'aware' in this case is the difference between 'following the meaning of a conversation' (aware) and 'I was woken up by people talking' (unaware, but the noise still woke the sleeper).

JC's podcast was very useful, but as it applies to this case it just clarifies that 'passive Perception' does not apply to a sleeper. It says nothing about an active Perception check to find out if a noise awakens a sleeper.

Second, your willingness to engage the fortune mechanic with reference to the assassin's DEX (Stealth) check seems to assume that the task of sneaking up on a sleeping creature wouldn't be a very easy task, even for a trained assassin. IME, it's very easy to avoid the notice of a sleeping person if that's your goal. And even if you aren't trying to avoid notice and are instead trying to accomplish some task that makes a loud noise, the sleeping person still won't notice you until after s/he is first awakened by the sound. For example, if I come home from work late, and someone is asleep in an adjoining room, it's very easy for me to stay quiet and avoid awakening that person, but if I start doing the dishes because the kitchen was left a mess, it's quite possible that the noise I make will wake up the sleeper.

It turns out that we subconsciously train ourselves to be awoken by some things while sleeping through other things; the volume of the noise is not the only factor. My example earlier in the thread was about sleeping through loud traffic noise while being instantly awoken by the broom handle tapping the kitchen ceiling. We can train ourselves to ignore the regular late night shenanigans of our housemates and still wake up to an intruder.

For fun, I thought it might be interesting to lay out the mechanical differences between our approaches. Your method results in four possible outcomes.

1. The assassin wins the DEX/WIS contest and initiative. S/he is unnoticed, and, when combat begins, the still-sleeping creature is surprised. The assassin attacks with advantage if within 5 feet of the prone creature, and any hit is critical. The sleeping creature awakens upon taking damage and remains surprised until the end of its turn.

2. The assassin wins the DEX/WIS contest, but the sleeping creature wins initiative. The assassin is unnoticed, and the sleeping creature is surprised at the start of combat, but, although it remains asleep, it ceases to be surprised at the end of its turn but can't take reactions because it's still asleep. The assassin must be within 5 feet of the prone, sleeping creature not only to gain advantage on the attack but to score a critical hit as well. Upon taking damage, the creature awakens.

3. The sleeping creature wins the DEX/WIS contest, but the assassin wins initiative. The sleeping creature notices the assassin and wakes up before combat starts. The assassin attacks the still-prone creature with advantage if within 5 feet. On its turn, the creature can stand up from prone and/or move and act.

4. The sleeping creature wins the DEX/WIS contest and initiative. It notices the assassin and wakes up before combat starts. On its turn, it can stand up from prone and/or move and act normally. The assassin's attack may have advantage if the assassin remains unseen, but otherwise the assassin attacks as normal.

My method, on the other hand, produces two outcomes that are possible.

1. The assassin wins initiative. S/he is unnoticed, and when combat begins, the creature is awakened and surprised. The assassin attacks with advantage if within 5 feet of the prone creature, and any hit is critical. The creature remains surprised until the end of its turn. (Note that this is mechanically identical to your outcome 1., the only difference being that I have the sleeping creature awaken to be surprised, which is narrative rather than mechanical.)

2. The sleeping creature wins initiative. The assassin is unnoticed, and when combat begins, the creature is awakened and surprised. The creature stops being surprised at the end of its turn and can take reactions on the assassin's turn. The assassin attacks with advantage if within 5 feet of the prone creature but doesn't auto-crit. (This is similar to your outcome 2., except that the creature gets to take reactions by virtue of having won initiative.)

The main difference in outcomes I see here doesn't stem from the timing of the creature's awakening. It stems from the fact that in my approach the sleeping creature is automatically surprised due to being unaware of its surroundings.

So, if the results are similar enough that it really isn't a problem, the the results are a wash. The only difference is then how much sense it makes. I'm really bothered by the 'auto-wake' thing. This is a game after all. These things are the exciting bits.

How does skill in Perception make someone more likely to have a full bladder? Do low WIS/low Perception characters in your games frequently wet themselves?

How does an assassin's botched DEX (Stealth) check cause a drunk to smash a bottle outside? Or is it the sleeping creature's high Perception that allows it to be roused by the constant smashing of bottles that exists in your game-worlds?

No more than an assassin quietly drawing a blade automatically causing light to flash which automatically wakes sleepers in a 30 foot radius!

If we're looking for the correct place for the narrative in between the dice rolling, then it comes in to explain why our roll just failed or succeeded, and you can think up a plausible reason on the fly; bladder, bottle, whatever.

This is how RPGs and their funny little dice work. We don't just decide that bladders are full, bottles are broken and/or light flashes before any dice are rolled, in such a way that the dice are never rolled! We don't have a game with skills that determine how well we do things and then just decide how well we do things so we never roll the dice!
 

Hriston

Dungeon Master of Middle-earth (He/him)
You and I both agree that, while unconscious creatures are 'unaware', their senses continue to function. Conceptually, being 'aware' in this case is the difference between 'following the meaning of a conversation' (aware) and 'I was woken up by people talking' (unaware, but the noise still woke the sleeper).

I disagree. You can follow the meaning of a conversation you hear in your sleep, and it can even weave its way into your dreams, but you aren't consciously aware that you're doing so, which to me is the important distinction. When I DM, I don't describe to the players things of which their characters are unaware. I limit myself to that which the PCs perceive consciously. So if your character is awake, I would describe to you the conversation your character overhears. If your character is asleep, however, the conversation would remain unknown to you. If I, as the DM, determine that the conversation wakes you up, then you become aware of the conversation from that point forward.

JC's podcast was very useful, but as it applies to this case it just clarifies that 'passive Perception' does not apply to a sleeper. It says nothing about an active Perception check to find out if a noise awakens a sleeper.

It doesn't need to. It is explained on p. 58 of the Player's Basic Rules that "[a]n ability check tests a character's or monster's innate talent and training in an effort to overcome a challenge. The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure." A sleeping character is not making an effort and is not attempting to notice other creatures. Closing your eyes and falling asleep is a very poor way of keeping watch. If you, as DM, wish to consult a sleeping creature's Perception bonus, or add it to a random roll, to set a DC for a sneaking creature's Stealth check, that's your prerogative, but you might as well pick a number any other way for how much it has to do with what the sleeping creature is doing. It certainly doesn't fit the description of an ability check.

It turns out that we subconsciously train ourselves to be awoken by some things while sleeping through other things; the volume of the noise is not the only factor.

That's why I have a short list of events which automatically awaken a sleeping creature. Loud noise is only one of them. Combat is another.

So, if the results are similar enough that it really isn't a problem, the the results are a wash. The only difference is then how much sense it makes. I'm really bothered by the 'auto-wake' thing.

The results are not the same. You're asking for a check that measures a creature's effort to be aware of its surroundings from a creature that isn't aware of its surroundings and isn't trying to be. How do you reconcile those two things in a way that makes sense?

If we're looking for the correct place for the narrative in between the dice rolling, then it comes in to explain why our roll just failed or succeeded, and you can think up a plausible reason on the fly; bladder, bottle, whatever.

This is how RPGs and their funny little dice work. We don't just decide that bladders are full, bottles are broken and/or light flashes before any dice are rolled, in such a way that the dice are never rolled! We don't have a game with skills that determine how well we do things and then just decide how well we do things so we never roll the dice!

Again, I'd refer you to the section of the DMG entitled "The Role of Dice" (p. 236). I get that you're a proponent of the style of play called "Rolling with It". The drawback to this playstyle in my view, and the view of the game developers, is that roleplaying suffers when everything is decided by the dice and the choices the players make at the table don't matter. Choose to keep watch for sneaking creatures? Roll a Perception check. Choose to go to sleep? Roll a Perception check anyway! This is a matter of playstyle, and for you to suggest that my preferred playstyle is incorrect is badwrongfun-ing. I certainly don't need a lecture from you on how RPGs work.
 

Arial Black

Adventurer
I disagree. You can follow the meaning of a conversation you hear in your sleep, and it can even weave its way into your dreams, but you aren't consciously aware that you're doing so, which to me is the important distinction. When I DM, I don't describe to the players things of which their characters are unaware. I limit myself to that which the PCs perceive consciously. So if your character is awake, I would describe to you the conversation your character overhears. If your character is asleep, however, the conversation would remain unknown to you. If I, as the DM, determine that the conversation wakes you up, then you become aware of the conversation from that point forward.

We are saying the same thing here, just using different words.

It doesn't need to. It is explained on p. 58 of the Player's Basic Rules that "[a]n ability check tests a character's or monster's innate talent and training in an effort to overcome a challenge. The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure." A sleeping character is not making an effort and is not attempting to notice other creatures. Closing your eyes and falling asleep is a very poor way of keeping watch. If you, as DM, wish to consult a sleeping creature's Perception bonus, or add it to a random roll, to set a DC for a sneaking creature's Stealth check, that's your prerogative, but you might as well pick a number any other way for how much it has to do with what the sleeping creature is doing. It certainly doesn't fit the description of an ability check.

Your idea, that PCs are only allowed to make checks if they are deliberately choosing to put effort into doing so, is a fundamental misunderstanding of the text on Ability Checks (PHB p172), which states:-

"An ability check tests a character’s or monster’s innate talent and training in an effort to overcome a challenge. The DM calls for an ability check when a character or monster attempts an action (other than an attack) that has a chance of failure. When the outcome is uncertain, the dice determine the results"

It's not that the creature is deliberately, consciously trying to overcome a challenge (though it usually is), but the the Ability Check itself is what tests the creatures 'innate talent and training'. There is absolutely no requirement for the creature to be doing something deliberately and consciously in order to have their innate talent and training tested by means of an ability check! It's very common, for example, for a DM to ask for Perception checks to find out if you heard something without you ever stating that you were trying to hear it! The DM might ask for an Insight check to notice that someone is behaving strangely, without you ever stating that you were on the lookout for strange behaviour.

What ability checks are in the game for is for situations "When the outcome is uncertain, the dice determine the results".

Therefore, the idea that sleeping creatures are not permitted ability checks is simply not the case.

That's why I have a short list of events which automatically awaken a sleeping creature. Loud noise is only one of them. Combat is another.

We have a situation where stimulous that may or may not be picked up by a creature's senses may or may not wake it. What does the game itself expect us to do? I'll quote it again:- "What ability checks are in the game for is for situations when the outcome is uncertain, the dice determine the results".

The problem with the way you do it is that you take a situation which is rife with uncertainty and just....decide. No uncertainty. That doesn't make sense.

Further, your criteria for choosing whether or not a creature wakes is completely divorced from the things which do determine (largely) whether or not a creature wakes due to the stimulous: how loud or quiet the stimulous (Stealth check) and how sharp the senses of the sleeper (Perception check).

That's two good reasons why this idea of yours is a poor choice.

You're asking for a check that measures a creature's effort to be aware of its surroundings from a creature that isn't aware of its surroundings and isn't trying to be. How do you reconcile those two things in a way that makes sense?

As above, I'm using an ability check to test the innate talent and training of the sleeper's senses, and contesting it with the innate talent and training of the assassin to avoid waking the target. You already admit that the sleeper's senses are picking up information from their environment, otherwise 'noise' (however loud) would not be detected and therefore could not waken the sleeper.

It all makes sense. ;)

Again, I'd refer you to the section of the DMG entitled "The Role of Dice" (p. 236). I get that you're a proponent of the style of play called "Rolling with It". The drawback to this playstyle in my view, and the view of the game developers, is that roleplaying suffers when everything is decided by the dice and the choices the players make at the table don't matter. Choose to keep watch for sneaking creatures? Roll a Perception check. Choose to go to sleep? Roll a Perception check anyway! This is a matter of playstyle, and for you to suggest that my preferred playstyle is incorrect is badwrongfun-ing. I certainly don't need a lecture from you on how RPGs work.

First, it's still a meaningful choice of whether to stay on watch or go to sleep. Those on watch benefit from passive Perception while sleepers don't, and sleepers have disadvantage on their Perception checks for, y'know, being asleep. It's been a long time since the disadvantage thing was mentioned in this thread, but it has been mentioned multiple times.

Second, the fact that dice are rolled to resolve the exciting stuff doesn't mean the player's choices don't matter! Sure, it's not like chess where there is no randomness; it's more like a game of bridge where the card distribution is random but your skill includes taking account of the randomness. We know, as players, that d20s get rolled. This does not mean that our choice to attack the ogres or the dragon has no effect. It doesn't mean that the choice to either sleep or stay on watch has no effect just because dice are involved. Our choices do have an effect, even if that effect is to skew the odds in our favour. They are meaningful choices.

Third: badwrongfun. These forums take accusations of 'badwrongfun' as very poor form. People play what they want to play and it's nobody else's business. I get that.

However, I believe it's fair to comment when someone says "I do it this way" if 'this way' seems absurd or unfair. You've put the idea out into the forum, people are going to comment.

I can imagine my own frustration if I were playing either an assassin or the sleeping victim of one and the DM rendered my choices as a player moot by ignoring all those skill proficiency/expertise choices I'd made to represent their strengths by simply ignoring the game system and choosing who wins and loses, using criteria that don't match the situation.
 

Hriston

Dungeon Master of Middle-earth (He/him)
There is absolutely no requirement for the creature to be doing something deliberately and consciously in order to have their innate talent and training tested by means of an ability check!

Only if you completely ignore the part that says an ability check is called for when a character attempts an action and tests talent and training when a character makes such an effort. You're just ignoring that.

Those on watch benefit from passive Perception while sleepers don't, and sleepers have disadvantage on their Perception checks for, y'know, being asleep. It's been a long time since the disadvantage thing was mentioned in this thread, but it has been mentioned multiple times.

You give a sleeping creature as good a chance of noticing hidden creatures as a fully awake person has of spotting something in dim light, and a better chance than a fully awake person engaged in drawing a map, foraging, navigating, or tracking. Huh.

These forums take accusations of 'badwrongfun' as very poor form.

Then don't make them. Don't tell me my way of playing is incorrect, especially when it's what the book recommends while the way you play is called out as having a negative effect on roleplay.
 

Arial Black

Adventurer
Only if you completely ignore the part that says an ability check is called for when a character attempts an action and tests talent and training when a character makes such an effort. You're just ignoring that.

"All poodles are dogs, but not all dogs are poodles".

If a character deliberately attempts an action then we certainly can and do make ability checks, so the text is not wrong. But the text in no way limits tests of talent and training to situations where the creature being tested must be consciously trying to do something.

You give a sleeping creature as good a chance of noticing hidden creatures as a fully awake person has of spotting something in dim light, and a better chance than a fully awake person engaged in drawing a map, foraging, navigating, or tracking. Huh.

In previous systems there would be various positive and negative modifiers to be collated for various situations. In 5E the advantage/disadvantage system has both strengths and weaknesses, and this is one of the weaknesses.

If my PC wears a magic ring that gives him advantage on Perception checks, if the DM said that being asleep gives me disadvantage and they cancel out, I wouldn't think that the system was being unfair.

Then don't make them. Don't tell me my way of playing is incorrect, especially when it's what the book recommends while the way you play is called out as having a negative effect on roleplay.

I don't agree that you're playing the way the book recommends, and in a thread about the rules on this subject I'm justified in saying you're doing it wrong in rules terms, to inform those reading the thread.

I'm not saying, "You're having fun wrong". I'm saying, "The way you do it is not consistent with either the rules or the intent of the game. Those of you reading this thread to try to understand what the rules are should take note".
 

Hriston

Dungeon Master of Middle-earth (He/him)
"All poodles are dogs, but not all dogs are poodles".

If a character deliberately attempts an action then we certainly can and do make ability checks, so the text is not wrong. But the text in no way limits tests of talent and training to situations where the creature being tested must be consciously trying to do something.

The text absolutely does limit ability checks to such situations! Here's the full text (with the relevant part in boldface): "An ability check tests a character's or monster's innate talent and training in an effort to overcome a challenge." That emphasized phrase limits when a creature's talent and training are measured by an ability check. Only "in an effort to overcome a challenge" is the result of an ability check applicable to the outcome of the situation in question. The corresponding, also true statement is that an ability check does not test a character's or monster's innate talent and training in the absence of an effort to overcome a challenge. So when considering whether to call for an ability check to determine if a sleeping creature notices an approaching attacker, the DM should take into account whether the sleeping creature is making an effort to do so. Considering that the last action declared by the creature's player was for the creature to go to sleep, an action that is actually the opposite of staying alert and aware of one's surroundings, the answer is that no ability check is warranted in making that determination.

I don't agree that you're playing the way the book recommends, and in a thread about the rules on this subject I'm justified in saying you're doing it wrong in rules terms, to inform those reading the thread.

I'm not saying, "You're having fun wrong". I'm saying, "The way you do it is not consistent with either the rules or the intent of the game. Those of you reading this thread to try to understand what the rules are should take note".

Well, then you're misleading your audience. The "Rolling With It" playstyle you advocate comes with the disclaimer that it discourages roleplaying, yet you've told me and the impressionable readers you imagine you're helping that to play any other way is not "correct". The truth is that I and others like myself prefer a game where the dice are used judiciously and dramatically, and not for determining everything under the sun from the timing of a creature's bodily functions to the random sounds of a city street. In my games, establishing such colorful elements is left within the purview of the DM.
 

Ovinomancer

No flips for you!
The text absolutely does limit ability checks to such situations! Here's the full text (with the relevant part in boldface): "An ability check tests a character's or monster's innate talent and training in an effort to overcome a challenge." That emphasized phrase limits when a creature's talent and training are measured by an ability check. Only "in an effort to overcome a challenge" is the result of an ability check applicable to the outcome of the situation in question. The corresponding, also true statement is that an ability check does not test a character's or monster's innate talent and training in the absence of an effort to overcome a challenge. So when considering whether to call for an ability check to determine if a sleeping creature notices an approaching attacker, the DM should take into account whether the sleeping creature is making an effort to do so. Considering that the last action declared by the creature's player was for the creature to go to sleep, an action that is actually the opposite of staying alert and aware of one's surroundings, the answer is that no ability check is warranted in making that determination.



Well, then you're misleading your audience. The "Rolling With It" playstyle you advocate comes with the disclaimer that it discourages roleplaying, yet you've told me and the impressionable readers you imagine you're helping that to play any other way is not "correct". The truth is that I and others like myself prefer a game where the dice are used judiciously and dramatically, and not for determining everything under the sun from the timing of a creature's bodily functions to the random sounds of a city street. In my games, establishing such colorful elements is left within the purview of the DM.

1) you don't think that the sleeping creature wouldn't desperately like to hear the approaching assassin intending to kill him, but would find it challenging on account of being asleep?

b) so, a character that declares they have no intention of becoming aware of an assassin by declaring they go to sleep is still rudely awakened from this declaration by the DM on an arbitrary basis? Why cannot the sleeping character attempt an ability check to stay asleep in the face of combat? Surely, this is a challenge?

iii) rolling to see if you awaken before the assassin slips a dagger between your ribs is not a dramatic moment?
 

Caliban

Rules Monkey
RAW, sleeping renders you unconscious - deaf and dumb, unable to sense your surrounding. This is one thing I happily house rule - your senses of hearing and smell still work. In real life, things like smells or loud noises often wake people up.

Of course, in real life some people are effectively dead to the world - I had a roommate that wouldn't wake up if you sounded an air horn in his ear, you basically had to dump him out of bed. I, on the other hand, am a fairly light sleeper and any out of place noise will wake me up. I've also woken up because I smelled something burning.

Simplest way to handle this in-game is with a perception check - usually at disadvantage. Which is a house rule, and I only apply to people who are "naturally" asleep - not ones knocked unconscious or magically put to sleep.
 
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Hriston

Dungeon Master of Middle-earth (He/him)
1) you don't think that the sleeping creature wouldn't desperately like to hear the approaching assassin intending to kill him, but would find it challenging on account of being asleep?

Can you please phrase this in the form of a question? Also, I find your use of a double negative confusing. Was that intentional?

b) so, a character that declares they have no intention of becoming aware of an assassin by declaring they go to sleep is still rudely awakened from this declaration by the DM on an arbitrary basis?

The DM is the game's arbitrator, so this would seem like the DM's proper role.

Why cannot the sleeping character attempt an ability check to stay asleep in the face of combat? Surely, this is a challenge?

None of the six ability scores measures an ability to stay asleep, so no.

iii) rolling to see if you awaken before the assassin slips a dagger between your ribs is not a dramatic moment?

Waking up right before the assassin strikes is a dramatic moment. Not waking up while the assassin slips a dagger between your ribs is not a dramatic moment. You just die. Why let the dice take away a dramatic moment and act like it's the character's fault because s/he failed an ability check?
 
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