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So say I'm going to ambush an orc. I successfully sneak up on him and I attack. The DM determines that the orc is surprised. The orc happens to get an initiative roll of 19, while I get a 10. How would this work? I can only think of two reasonable resolutions to this.

  1. The orc, having a higher initiative, goes first. Since he's surprised, he does nothing. Then it's my turn. If the orc survives my attack, it is now his turn, and being that the orc has already gone through his round of surprise, he can now attack me or whatever, and combat proceeds as normal.
  2. I, having started the combat, go first. If the orc survives my attack, but he is surprised, so he does nothing. It is now my turn again, I attack again. If the orc survives my second attack, it is now his turn, and being that the orc has already gone through his round of surprise, he can now attack me or whatever, and combat proceeds as normal.

Which one of these is correct? neither? Does starting combat secure me a turn/action at the start of initiative order like in option 2? If option 1 is correct, could I ready an action to shoot the orc, effectively granting me a similar first attack as in option 2?

Sorry if this makes no sense.

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Interpretation 1 is correct.

The rules of surprise are described here in the basic rules:

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn't notice a threat is surprised at the start of the encounter.

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.

Surprise occurs within initiative. If you declare a combat action (e.g. an attack), you roll initiative before the combat action is resolved. If a creature is surprised, that simply means it can't take actions (or bonus actions; "anything that deprives you of your ability to take actions also prevents you from taking a bonus action") on its first turn of combat, and it can't take reactions (such as opportunity attacks) until its first turn is over.

Any combat action would occur within initiative. You can't ready an attack outside of combat; otherwise, literally every character would have an attack readied as they wander around a dungeon. The point of initiative is to resolve the order in which creatures that are prepared for combat (i.e. not surprised) act.

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    \$\begingroup\$ Thanks! Accepted because you answered my question on readying before combat as well as my main question. \$\endgroup\$ – Ponggoleechee Jun 25 '18 at 2:53
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Your first interpretation is correct.

Initiative is rolled as always. If the orc rolls higher than you he is still surprised and does nothing. If the orc rolls lower than you and you stab him he is still surprised and gets to act and move only in the next round.

Look at the following snippet on surprise (taken from 5eSRD.com):

[...]

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. [...]

Emphasis mine.

The only difference the initiative of the orc makes would be attacks of oportunity. If the orc goes after you, you can run in, stab him and then swiftly move out of his reach (if you have enough movement left) without him able to retaliate; if, however, he did have his surprise turn before you move you'd get counter-stabbed if you moved out of his reach after attacking.

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    \$\begingroup\$ Higher initiative also means effectively you get 2 attacks against the orc before it gets a real turn. This can be a huge advantage. \$\endgroup\$ – SeriousBri Jun 20 '18 at 7:39
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RAW, Situation 1 is Correct

From Page 189 of the PHB (Chapter 9: Combat)

The DM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the DM compares the Dexterity (Stealth) checks of anyone hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

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.

So, whomever rolls the higher initiative still goes first. If it's the surprised creature, however, they cannot effectively take a turn.

However, the GM has the ability to change the rules in any way they see fit, and one example that I've seen some GMs do is ruling that Surprised creatures get a penalty to Initiative rolls (because they can't react as fast.)

The GM can also apply situational/circumstantial bonuses depending on the situation. For example, a Rogue attacking from Stealth with a crossbow might get an additional +2 on their initiative role, but a combatant affected by the Slow spell (such as from an Artifact) may roll with a -3 penalty.

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