How does the Gloom Stalker ranger's Dread Ambusher feature interact with Surprise?

Question

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.

Answer 1

A surprised creature remains surprised until the end of their turn on the first round of combat

Related:

• How often during combat can you be Surprised?
• What happens when your group is victim of a surprise attack but you can't be surprised?
• Readying an action for sneak attacks in surprise rounds
• What's the correct way to determine turn order in this situation?

and especially:

• At which moment does the 'Surprised' state disappear?

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:

1. creatures who are surprised - meaning they were surprised at the start of the combat and their turn comes after the Gloom Stalker ranger/Assassin rogue.
2. everyone else - which includes both those who were surprised but are no longer surprised because they have had their turn already, and those who were never surprised.

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.

Answer 2

The creature remains surprised.

There aren't any special rules on the Dread Ambusher or Assassinate features that would cause a creature to stop being surprised. Since there aren't any special rules, the creature remains surprised until the end of their turn as normal.

If you aren't sure what the surprised state is, please refer to this question:
At which moment does the 'Surprised' state disappear?