In D&D 5e, if a Gloom Stalker Ranger uses their Dread Ambusher feature's secondary attack on a creature during a surprise round (whether on the same target or a different one), is that creature still considered surprised?
This is important if the character is multiclassed with Assassin rogue, because Assassins auto-crit when hitting a surprised creature.
Best Answer
A surprised creature remains surprised until the end of their turn on the first round of combat
Related:
and especially:
If you take from these one thing and one thing only it should be this:
There is no "surprise round" in D&D 5e!
There is only the first round of combat during which none, some or all combatants may be surprised until the end of their turn.
When it is the Gloom Stalker ranger/Assassin rogue's turn during the first round there are only two types of creatures:
If the Gloom Stalker ranger/Assassin rogue chooses, on their turn, to attack a surprised creature, then that creature remains surprised because they haven't had their turn yet. It doesn't matter if the Gloom Stalker ranger/Assassin rogue attacks once, twice or seventy-three times - the creature is surprised during each and every attack.