In D&D 5e "Surprise" is a condition that can affect a creature during the first round of combat, only until the end of their turn:
[... T]he GM 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. - PHB 189
Does the action that causes the surprise count as part of the round, though?
Say Renee, a rogue, achieves a stealth check of 22, easily beating an orc sentry's passive perception. She sneaks directly behind him and stabs him in the back. Surely the orc isn't surprised at all until the dagger hits him (or if Renee misses, she fumbles around behind him or something).
What I think it really boils down to in the end is: when is initiative rolled? If (in our example) initiative is rolled before Renee's attack hits (or misses) how can we justify the orc recovering from his surprise before the action that triggered said surprise even occurs, should he roll better than Renee on his initiative?
I'd like to go with initiative is rolled immediately following whatever event began the encounter (which could be an attack, but is likely to often be something else wherever surprise isn't intended), but I can't find any documentation to support this stance.
Why Does Anyone Care?
There are many reasons you might want someone to be surprised while you're attacking - in this example if Renee is over L3 (and took the Assassin archetype) she'll get 'Assassinate' if the orc is surprised, and 'Death Strike' if she's over L17. That's a lot of potential extra damage!
J.E also pointed out that if the orc is surprised, Renee will be able to retreat and hide, without having to take the disengage action as her bonus action to avoid an attack of opportunity. Of course, there's no way for her to know whether the orc is surprised or not at that stage, so trying this would be a bit of a gamble...