D&D 5E Surprise and Sneak Attack

[giore]

reviving dead post because I find this issue especially interesting.

The real issue is in how the assassin subclass is worded, which is a total mess.

The exact ruling for surprise in 5e is counterintuitive and a bit weird, but once you understand how it works it actually makes sense.

The surprise mechanic is meant to define a tactical advantage so to reward strategic thinking (or punish the lack of it).
If you prepared, planned ahead and succeeded in ambushing your target, you basically get way ahead in the action economy, which is huge in 5e.
You strike out of nowhere, before anything is resolved initiative is rolled, all the creatures unable to detect you now have "the surprised status".

Then everyone acts per initiative order, as usual.
All the creatures with the surprise status, though, can only use their turn "to stop being surprised", which is an enormous advantage.

Do they come before you in the initiative order? Well, now they know you're there, but they spent their first turn doing nothing.

Did you get to go first? Even better, the creatures can't even take reactions until after their first turn.

The difference between the two scenarios is minimal. In both situations a succesful ambush means a lot of free attacks and a very evident advantage for the ambushers.
Using invisibility, stealth, or enchantment spells or whatever it's absolutely worth it, it almost always defines the outcome of the encounter.

I personally dislike this system, but I admit that even if it feels clunky it actually works as intended.

The problem is that the way the assassin is designed goes against the core rules of the game, it makes absolutely no sense. It's so bad it's offensive, because the assassin it's actually a great subclass, but it makes the worst possible use of the game mechanics. Seriously.

The whole point of the class is using planning and role playing to take down enemies instead of engaging in "normal combat". Every single feature the assassin has revolves around this concept.
If you are inventive, smart and plan together with your party, you can turn combat encounters in puzzles or in social encounters. This means that the assassination actually RESOLVES OUT OF COMBAT, because you spend most of the time preparing for it. This is obviously balanced by the assassin's complete lack of proper combat skills. Outside a narrow and very specific situation, the assassin is by far inferior to any other rogue subclass. He literally has 0 combat bonuses and 0 exploring or utility oriented skills.

This a super cool choice because IT FORCES YOU TO COMMIT to a role play heavy style, rewarding you for interacting with the game world and putting you at a steep disadvantage if you don't.
So you have to take everything in account: you stack bonuses, buffs and potions to rise your chances to hit as much as possible, you stack damaging buffs, poisons etc, to be sure to do maximum damage, you study a strategy to make sure to reach your target without alerting it.
You make sure you have advantage, you make sure you can cause surprise on your target.
you plan, gather and expend resources, build and optimize your character to do so.
You never have a 100% chance of success, but you can do a lot to rise your chances by as much as possible.
Because it's what the class is designed to do, because it's what you wanted to do, because it's super fun.

BUT THEN, THE WHOLE MECHANIC FALLS APART.

Because the assassin absolutely needs to activate its ability, or all the planning done means nothing.
If you have to strike while the target is still surprised, then you need to make sure you have a higher initiative than it, right? yes of course. TOO BAD, YOU CAN'T.
THERE ARE ALMOST NO WAYS TO INFLUENCE INITIATIVE ROLLS.
You just can't prepare for it. And if you fail, you're done.
The few that exist HAVE NOTHING TO DO WITH PLANNING, strategy or preparing. And almost all of them ARE NOT ACCESSIBLE TO THE ASSASSIN. The only thing you can do is take the alert feat. Period. If you don't, the class is unplayable, because there would be NO WAY to influence the outcome of the roll that decides if the assassination works. The whole class is based on roleplaying, planning, being sneaky and strategic, it's all about thinking in advance. But all the work you do is actually pointless, because in the end you just hope to get lucky and roll higher than your target, which could very well have dex modifiers not so different from yours.

I hope you see now why the wording of the assassin MAKES ABSOLUTELY ZERO SENSE. it's so dumb it's infuriating.
It's horrible design. And it's even more infuriating because the class is actually well made and balanced, but the wording makes it unplayable., unless your DM decides to change the surprise mechanics.

It would take so little like to fix it, like: "all your attacks toward creatures who have been surprised this round are critical hits" or a different variant with different implication "during the first round of combat all your strikes directed to creatures that haven't taken any actions yet are critical hits". with this wording your planning will always work as intended if you did it properly. You can still miss, you can still roll low, you're taking CALCULATED risks to get a great reward, which is very different than "you plan for hours then toss a coin and hope it wasn't all for nothing".

Or they could leave the core ability as it is and add another ability like the one the 3.5 assassin had: "if you study your target for at least 3 rounds while being no more than 30 ft from it and without the target being aware of you or considering you a threat you get advantage on the next initiative roll".
This way you can do something! You can influence the roll, if you plan thoroughly and find a way to decieve your target or prepare a trap. That's what assassins do both in games and real life!

Or they could even leave things as random as they are and add a greater reward.
"The assassin's critical strikes multiply the total number of dice by 3 instead of by 2". If the intent was to design a class that employs extremely risky strategies, then rise the stakes! This is even more flavorful because ithighlights the assassi's anatomical knowledge and proficiency in murder.

I hope i made my point clear...

 

[Lyxen]

Our table's solution for this is simple, we allow characters to ready actions out of combat. This allows an assassin, if he does his preparation job properly, to be able to attack as a reaction (for example when the target comes into view) which completely solves the problem. It also has the advantage to allow a victim to prepare itself for an assassination attempt the the assassin has been careless and unlucky. And it also takes care of the frustration of players anticipating a fight during a social situation and who don't like to be told "I don't care if you were ready for treachery during the negotiation, just roll for initiative".

Of course, as per the rules, the readied actions need to be specific and the triggers perceivable, and of course a given trigger needs to happen, which might mean - if you were wrong about what you anticipated - that you will lose your readied action, but it encourages players to be pro-active.

 

[Greenstone.Walker]

THERE ARE ALMOST NO WAYS TO INFLUENCE INITIATIVE ROLLS.

Bardic Inspiration.
Guidance spell.
Enhance Ability spell.
Stone of Good Luck magic item.
Ioun Stone of Agility magic item.
Ioun Stone of Mastery magic item.
Weapon of Warning magic item.
Sentinel Shield magic item.
Diviniation Wizard Portent.
Alert feat.
The Bard feature Jack of All Trades.
The Barbarian feature Feral Instinct.
The Fighter feature Remarkable Athlete.
The Ranger feature Dread Ambusher.
The Rogue feature Rakish Audacity.

And of course, Inspiration.

I'm not sure I'd call that "almost no ways."

 

[giore]

Our table's solution for this is simple, we allow characters to ready actions out of combat. This allows an assassin, if he does his preparation job properly, to be able to attack as a reaction (for example when the target comes into view) which completely solves the problem. It also has the advantage to allow a victim to prepare itself for an assassination attempt the the assassin has been careless and unlucky. And it also takes care of the frustration of players anticipating a fight during a social situation and who don't like to be told "I don't care if you were ready for treachery during the negotiation, just roll for initiative".

Of course, as per the rules, the readied actions need to be specific and the triggers perceivable, and of course a given trigger needs to happen, which might mean - if you were wrong about what you anticipated - that you will lose your readied action, but it encourages players to be pro-active.

That makes a lot of sense.

I just recently found out we were playing it all wrong.... Well at least not how we were "supposed" to.
We all come from 3.5 and we all took for granted that surpise meant "surprise rounds". It is functionally pretty much the same thing, a mechanic that rewards forward planning with free actions, but it's much simpler and more intuitive.
It took me a lot to understand why we were wrong, because the 5e assassin actually worked pretty well with the old surprise round!
Even the wording seemed to refer to the old ruling.
Still the class it's not perfect by any means and perhaps it's still a bit underpowered, but it allows you to do what the class was conceived to do: evil scheming for happy brutal murder.

It's a simple gimmick, but it's one of the reasons i fell in love with dnd.
I think this is what rules and mechanics should strive to do: encourage players to solve in game problems through their narrative skills.

This is also why i kind of care about the assassin and how to fix it, it's a prime example of how well thought rules can force you into deeper immersion

Ok, nerdy example no one asked for:
Some time ago I rolled an assassin shadow sorcerer, which on paper should have been severely lacking and also prone to be a cringey edge lord (or edge lady, in this case), but it actually came out as a fun, supportive and surprisingly reliable character. She's a "living plot device": she can dish out a ridiculous amount of punishment, but she needs to cooperate with the rest the party and work with them to set up the deadliest trap possible. On her own, she's fun to play, but not particularly powerful (and also pretty dumb).
The other players love her thematically, and actively build strategies requiring her assassination skills.
We even set a "combat password": when someone says the magic word, the assassin will drop her silly girly disguise and immediately alpha strike the closest enemy caster.

We're having fun together, and part of it comes from seeing the rules as a tool to enhance our collective narration

 

[Lyxen]

It took me a lot to understand why we were wrong, because the 5e assassin actually worked pretty well with the old surprise round!
Even the wording seemed to refer to the old ruling.

That's an unfortunate side effect of 5e's natural english reminding people of more technical jargon from previous editions, 3e in particular, there are quite a few cases like this.

Still the class it's not perfect by any means and perhaps it's still a bit underpowered, but it allows you to do what the class was conceived to do: evil scheming for happy brutal murder.

Yes, I think that's also a bit of the problem inherited from 3e, the mania of "builds" and comparing theoretical power of classes. The fact is that it's very rare when combat occurs in perfect condition anyway, and the circumstances always matter way more than theory, which in turn means that if you play your assassin right, the circumstances will favour you and he will feel right.

I think this is what rules and mechanics should strive to do: encourage players to solve in game problems through their narrative skills.

And they do, if people pay a bit more attention to the stories and narrative than to the RAW.

We even set a "combat password": when someone says the magic word, the assassin will drop her silly girly disguise and immediately alpha strike the closest enemy caster.

We had something like that in a LARP, if someone mentioned that his father had an officer rank in the military, we would all strike, but it never worked out, people did not pay enough attention and it frustrated our leader to no end...

 

[giore]

Bardic Inspiration.
Guidance spell.
Enhance Ability spell.
Stone of Good Luck magic item.
Ioun Stone of Agility magic item.
Ioun Stone of Mastery magic item.
Weapon of Warning magic item.
Sentinel Shield magic item.
Diviniation Wizard Portent.
Alert feat.
The Bard feature Jack of All Trades.
The Barbarian feature Feral Instinct.
The Fighter feature Remarkable Athlete.
The Ranger feature Dread Ambusher.
The Rogue feature Rakish Audacity.

And of course, Inspiration.

I'm not sure I'd call that "almost no ways."

I don't mean to be rude but:

5 of these are powerful and extremely costly magic items, some of which are not directly available to rogues without further investment in feats or multiclassing.
other 6 entries are from other classes and some of these features require a significant investment in other levels. Rakish audacity isn't feasible at all, since it's from another rogue subclass.

Alert feat i am aware of, it's a good option, but even this one is no small investment, if you think about it. The assassin really needs ASIs as soon as possible.

Inspiration shouldn't be something you can rely on (at least at my table is rare), but, yes, it works.

I admit i didn't think about bardic inspiration, but you still need someone else to grant it to your murderboi at the right time.

Same with the spells (guidance is actually a good idea though). There also are other spells that could do the trick, like gift of alacrity, which you can obtain through the fey touched feat (which is arguably the best option here).

NONE of these options is something the assassin has access to by default and all of them require hard choices (multiclassing for several levels, giving up juicy ASIs for feats) just to not suck.
Same with the magic items, the one's that boost initiative have exorbitant prices and you're unlikely to see one before tier 3 (again, that's how we usually roll).
I personally think that being forced to invest some of the most valuable resources you have just to make the class do what it was supposed to do on its own it's the sign of a huge design problem.

The issue here is that you can prepare and work in advance to obtain a reliable advantage on attack rolls, by sneaking around.
You can also get closer to your target by infiltrating and use deception and disguises.
You can also stack damage, with sneak attack, poisons, or any kind of weird multiclass combo or lots of different items, both cheap and not so cheap. The game mechanics allow you to properly prepare in pretty much every aspect and stack enough bonuses to sneak and hit reliably.
But you just can't do it that easily with initiative. You can't plan so to have a situation in which initiative will be favorable to you like you do with attack rolls. You can get some bonuses out of your build, take feats, multiclass, etc. thus giving up other really useful options. Multiclassing is especially taxing and can severly posptone the moment in which your killer kiddo will finally be viable.
Otherwise you can plan to totally depend on someone else's help, without which your subclass features are worthless.


And yes, there already are ways to make the assassin work and i really like the class. I'm actually playing one.
it's frustrating, though, that such a potentially flavorful and entertaining class needs so much work just to do bare minimum because it clashes with core game design features.
5e is good but has lots of weird flaws and "bugs" and i really hope they'll fix this one like they fixed the ranger and (kind of) fixed the sorcerer with tasha's items

 

[giore]

Yes, I think that's also a bit of the problem inherited from 3e, the mania of "builds" and comparing theoretical power of classes. The fact is that it's very rare when combat occurs in perfect condition anyway, and the circumstances always matter way more than theory, which in turn means that if you play your assassin right, the circumstances will favour you and he will feel right.

i think the mania for builds is not inherently a bad thing.
It can become a powerful mean to enhance player immersion. I recently tried some super cool ttrpg with amazing atmosphere and setting that were etremely light on rules (like Morkborg) and, to my surprise, i felt like they were way too light on rules!
I ended up caring way less for my character and the suspension of disbelief took way more effort to kick in, even though i was really enjoying the rest of the game.
Builds are one of the main ways through which players emotionally invest in their characters, a little build optimization mania i suppose can help rise the intensity up a notch. It's also one of the main reason people like me get so angry when some class or interactions get changed or doesn't live up to expectations...

Ok enough nerdy forums, back to being a productive adult

 

[NotAYakk]

reviving dead post because I find this issue especially interesting.

The real issue is in how the assassin subclass is worded, which is a total mess.

The exact ruling for surprise in 5e is counterintuitive and a bit weird, but once you understand how it works it actually makes sense.

The surprise mechanic is meant to define a tactical advantage so to reward strategic thinking (or punish the lack of it).
If you prepared, planned ahead and succeeded in ambushing your target, you basically get way ahead in the action economy, which is huge in 5e.
You strike out of nowhere, before anything is resolved initiative is rolled, all the creatures unable to detect you now have "the surprised status".

You do know you are inventing mechanics here?

Then everyone acts per initiative order, as usual.
All the creatures with the surprise status, though, can only use their turn "to stop being surprised", which is an enormous advantage.

This is not how 5e words surprised. This is you inventing mechanics. It is invented mechanics compatible woth 5e wording, but 5e does not dictate these mechanics.

Most importsntly, 5e does not describe a "surprised status" (like prone, petrified, etc), nor does it descrive when the status ends.

5e only describes when you are surprised at the start of combat. Mapping this to a status condition with specific effects and end conditions is something you invented, not what the 5e rules say.

As it happens, your invented mechanics mostly work, but you have noticed that it makes the assassin class not work. So, maybe, don't use the mechanics you invented?

 

[Plaguescarred]

Most importsntly, 5e does not describe a "surprised status" (like prone, petrified, etc), nor does it descrive when the status ends.

While being surprised is not a condition like the one you enumerated, it is some form of status where it's effect sets a timing and duration. 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.

An official ruling was made in Sage Advice Compendium as to the duration of being surprised;

For triggering the rogue’s Assassinate ability, when does a creature stop being surprised? After their turn in the round, or at the end of the round? A surprised creature stops being surprised at the end of its first turn in combat.

 

[Plaguescarred]

The surprise rules are fine as they are. I always said the problem lies in the Assassinate mechanic. The second benefit is too situational and should instead score a critical hit against any creature that was surprised by you during the first round. Like this, loosing initiative during a successful surprise would still be benefical to an assassin somehow.