In my game I'm playing as a assassin rogue and I have just reached level three. My question is if I attack something in my understanding I get my assassination feature. If we then roll initiative and I go before it do I get the assassination again or am I misunderstanding it?
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Welcome to the site! Take the [tour] when you get the chance. You seem to be misunderstanding how surprise works. This question goes into how surprise works. Does that help answer your question? – David Coffron Nov 03 '18 at 21:54
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it's more of a question of would I get the ability to do my assassination twice if I attacked and then after initiative went before it again. – joshua Nov 03 '18 at 21:57
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How are you getting to attack both before and after initiative? – Mark Wells Nov 03 '18 at 21:58
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2Please clarify how you are attacking before rolling for initiative in the first place. As currently written the whole situation is very confusing. – Purple Monkey Nov 03 '18 at 21:58
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there is a situation where we are not in combat and talking to some guards and I decide to attack we are not in combat and as far as I know its them getting surprised after that they are aware and combat starts with initiative being rolled – joshua Nov 03 '18 at 22:01
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I would suggest you and your group carefully read through the combat rules again. – Purple Monkey Nov 03 '18 at 22:05
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1See, for example, https://rpg.stackexchange.com/questions/115800/how-to-resolve-surprise-and-instant-actioning-initiating-combat – Mark Wells Nov 03 '18 at 22:08
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2Not a duplicate, but answered by How to resolve surprise and “instant actioning” initiating combat – MikeQ Nov 03 '18 at 22:10
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You only benefit from Assassinate once per combat
You seem to be misunderstanding how surprise works. You cannot attack before rolling initiative. When combat is imminent, the GM decides who is surprised, and even if someone in the combat is surprised, you still roll initiative first.
The GM determines who might be surprised... 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.
[...]
When combat starts, every participant makes a Dexterity check to determine their place in the initiative order.
Then during the turn where the creature is surprised, they still have a turn (they just can't act). This means that if you roll poorly on initiative, you may not get advantage from Assassinate even if they are surprised when combat starts (since they already had a turn):
You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet.
[emphasis mine]
It is generally understood (although not overwhelmingly clear), that a surprised creature ceases to be surprised when they take their first turn (even if they do nothing), so in order to benefit from Assassination you have to go before the target. They will not be surprised by the time your turn comes around so you don't get the guaranteed critical hit:
In addition, any hit you score against a creature that is surprised is a critical hit.
David Coffron
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Assassinate, which gives you advantage on the attack roll, applies against any creature that has not had a turn in the combat.
You only roll initiative once, at the start of combat. So when it's your turn, you get that advantage against any creature that has not yet had its own turn.
If that creature is also surprised (was not previously aware of your presence) then the hit is automatically a critical (see Player's Handbook page 189).
PJRZ
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