D&D 5E Surprise and initiative

One Boss and one assassin only combat

Then the rogue better win initiative if he wants advantage and instant criticals, or the boss target gets to react to the ambush and not get punked. The rogue still gets to take actions before the the target just doesn't get to benefit from one of his class abilities, not seeing a problem with that.
 

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A Reaction is not a Turn, so until the surprised creature gets it's turn it is surprised but still gets a reaction after the lost Surprised turn

but only from the creature that surprised it
 

Step 3. of Combat Step by Step: Everyone involved in the combat encounter rolls initiative, determining the order of combatants’ turns.

Surprise: 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.

The surprised characters roll for initiative just like everyone else, on their turn which can happen before anyone else involved in the fight goes they take no actions, but they still had a turn.
 


A Reaction is not a Turn

Take a second and read it again.

Step 3. of Combat Step by Step: Everyone involved in the combat encounter rolls initiative, determining the order of combatants’ turns.

Surprise: 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.

The surprised characters roll for initiative just like everyone else, on their turn which can happen before anyone else involved in the fight goes they take no actions, but they still had a turn.

You aren't taking a reaction, you have a turn you just can't act on it. After your turn is over you can take reactions if one is triggered. You can be surprised and still have a turn before anyone else in the fight, you just can't take any actions or move on your turn.
 

A Reaction is not a Turn
You are correct. But a turn spent doing nothing IS a turn, whether you spend the turn intentionally doing nothing, or you spend the turn doing nothing because you were surprised.

The Assassin may very well still be hidden, and still gain advantage because of that, or by spending Inspiration, or whatever. A 3rd level ability is not supposed to be the "I win" button. It is an excellent ability, as written. Don't Panic.

The Assassin should go first, he likely has a higher DEX. But sometimes, the fates conspire against us, and even our best laid plans fail: yes, you surprised the big boss, but when you jumped out of the shadows he happened to be looking right at you (his Initiative Roll was higher than yours). It happens - and if you hadn't surprised him, he would have spent that turn smacking you around, getting away, or buffing. Your carefully executed plan didn't have quite the dramatic effect you wanted, but it still had an effect. Rejoice, and maybe plan on picking up that Alert Feat...
 

Alert Feat is the first one to get, but may be after Stat increase

But if the Boss does not see the arrow coming until after it hits how does it get initiative
 

You are correct. But a turn spent doing nothing IS a turn, whether you spend the turn intentionally doing nothing, or you spend the turn doing nothing because you were surprised.

The Assassin may very well still be hidden, and still gain advantage because of that, or by spending Inspiration, or whatever. A 3rd level ability is not supposed to be the "I win" button. It is an excellent ability, as written. Don't Panic.

The Assassin should go first, he likely has a higher DEX. But sometimes, the fates conspire against us, and even our best laid plans fail: yes, you surprised the big boss, but when you jumped out of the shadows he happened to be looking right at you (his Initiative Roll was higher than yours). It happens - and if you hadn't surprised him, he would have spent that turn smacking you around, getting away, or buffing. Your carefully executed plan didn't have quite the dramatic effect you wanted, but it still had an effect. Rejoice, and maybe plan on picking up that Alert Feat...

But it could be coming in the Errata that it is a lost Turn and does not count as a turn and the surprised creature is bypassed in the round, but can take a reaction after it's lost bypassed turn
 
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Regardless, I think Paraxis is right in his reading of RAW. And I don't think we should debate if it's RAI.
Ultimately, the DM will decide, and can even decide knowing his choice may not technically be RAW. It gives Rogues a strong reason to actually invest in initiative, rather than just coast on their high Dex for it, and could lead to more interesting tactical choices.

I can say for me, I'm going to be more lenient with how I let my Rogue players use their abilities, until I see them being too powerful etc.

Trit
 


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