DND_Reborn
The High Aldwin
Ok, I have to make an assumption here: when you are no longer in darkness, the target cannot see you (has its back turned, etc.), right? Otherwise, if they can see you coming at all, after 5 feet you lose the advantage (the 5-feet rule of thumb was JC's advice) and none of your attacks would have advantage.A common scenario. A character is currently in darkness and hidden. The character moves 20 ft towards an enemy, and after the first 10 ft of movement, is no longer in the darkness. They then proceed to make two attacks. They complete their move by moving back into the darkness.
At what point does the character lose the benefit of stealth?
1) As soon as they first move out of the darkness. None of their attacks get advantage.
2) The first attack gets advantage, then they lose stealth.
3) Both attacks get advantage, then they lose stealth.
4) They maintain stealth the entire time
So, assuming they still don't see you coming....
1) If they see you coming and you have to move more than 5-feet (IMO and I agree with JC on this one), no.
2) YES.
3) No. As soon as you make an attack, you give yourself away unless you have a feature that overrides this.
4) No.
Also, when you say "move back into darkness", if you mean actual darkness, unless the target has darkvision they can't see you. Now, this does NOT mean you are "hidden", you have to make an opposed Dex (Stealth) check versus their Wis (Perception), they win ties, to be hidden again.