D&D 5E (2024) How do you handle surprised but won initiative?

Is there a way to achieve the same result by bending the rules to suit the fiction rather than bending the fiction (as narrated) to suit the rules?
Nothing is being bent. If you tell me that your fighter swings his sword, I might narrate a wide swing. A downward chop. Or something else. The narrations fit the mechanics. What I described above is simply a narration that fits the mechanic. That of someone unlikely to win initiative, winning and hitting the ambusher first.
 

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I can see the problem being easier to explain if there are several monsters trying to gain surprise. I know many DMs tend to roll initiative for groups of monsters and not by each monster. The math is likely better to hid if one roll was made and not several, like calling for a Perception check and one PC is bound to roll high enough. So having one PC react faster than the lot of monsters makes enough sense to narrate.

One monster hiding makes less sense. I do not have a problem with it though.
 


I strongly suspect the point is to nerf ambush strategies. Surprise is busted powerful in 5.0. Personally, I’m fine with that being the case, but I’d imagine the thinking was that advantage on initiative is still impactful without making surprise a near auto-win, and then DMs can feel more free to grant surprise (to either side of a combat) more freely since it isn’t basically a free win.
So the problem is actually the 3-round-combat. If a combat is on average 3 rounds, getting the "surprise round" removes more than 1/3 of the attrition of said combat (because usually in round 1 the most damage is done - and surprise rounds also usually give you advantage on the attacks because you were hidden which means you will usually remove some enemey NPCs/Monsters in the surprise round, making a medium or hard combat encounter easy).
But at the same time, I think this is a feature and realistic. If you surprise an enemy, that just be devastating for him.
 

There are plenty of movies and tv shows where a well hidden assasin gives away their position by chance.
A reflection on a sniper rifle without actually seeing the sniper.

Sometimes the bodyguard can react fast enough and uses shove on their protegee to get them out of danger.

In D&D terms:
Initiative is rolled.
Fighter has advantage on initiative and rolls higher than the assassin.
Attack with unarmed strike: shove prone option. And then using their body for +5 AC for 3/4 cover.
 

I run it where the moment the ambusher decides to attack, that initiates the roll. There are plenty of class abilities that nullify the disadvantage of being surprised, so it seems unfair to grant the ambusher a "free" attack given this is a class ability (I'm talking about advantage on initiative rolls). Call it a sixth sense or whatever, but it really just means they suddenly become aware that something is trying to attack them. If the source is hidden, they can use their action to try to detect the source of danger (perception vs. stealth roll). Other options include running for cover while warning the party. Plenty of ways to narrate the quick reactions and keen senses of a character.
How do the players feel knowing that they can't actually get an ambush off either?
 

How do the players feel knowing that they can't actually get an ambush off either?
Given we still most often get to go before the majority of enemies, fine. Getting an ambush is not all about going first (unless you’re an assassin or gloomstalker). It’s also positioning and getting a tactical advantage.
 

Given we still most often get to go before the majority of enemies, fine. Getting an ambush is not all about going first (unless you’re an assassin or gloomstalker). It’s also positioning and getting a tactical advantage.
Typically an ambush is a tactic one uses to get a major advantage over a superior foe you cannot, or would not want to, take on in a standup fight. By reducing the effectiveness of ambush to "maybe we win initiative" you undermine that, which means it is harder to have the PCs be able to choose to push their luck and go bigger risk for bigger reward.

Like I have said, the system works fine for simple surprise, but I think actual ambush tactics should be more effective and robust -- from any side employing them.
 

But if you're mounting an ambush, acting first is not at all the only way to be effective. Acting from a superior tactical position, starting the battle with spells and protection already in place, being hidden, being behind cover, etc.

The 2014 rule is really one-dimensional in this regard, it's such a massive advantage that you don't even have to bother with the rest. It always annoyed me.
 

Really, ambushes need their own subsystem, beyond a simple surprise check. There should be a way to quantify set up and resource expenditure.
 

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