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The Bugbear's Surprise Attack feature reads:

Surprise Attack: If the bugbear surprises a creature and hits it with an attack during the first round of combat, the target takes an extra 7 (2d6) damage from the attack.

Is it referring to the bugbear's first round of combat or the players'?

My players were clearing Cragmaw Castle in LMoP. They were in a long combat that went from room to room, then entered another room and got surprised by a bugbear. I wasn't sure if this triggered the surprise attack or not...

I assume it doesn't trigger and it's meant as if the Bugbear ambushes an unaware party, but I'd like to be sure.

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    \$\begingroup\$ a feat is a specific game term in 5e, this is not a feat, but a feature. \$\endgroup\$ – András Feb 14 at 6:55
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    \$\begingroup\$ Possible duplicate of Can a character be surprised mid-combat? \$\endgroup\$ – GcL Feb 14 at 14:07
  • \$\begingroup\$ Hello. The title might be more clear if you reworded it to be, "Does the Bugbear’s “Surprise Attack” feature apply on its first round of combat or the encounter?" \$\endgroup\$ – GcL Feb 14 at 14:22
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It is the same thing

The bugbear and the players each have a turn in the first round.

The Order of Combat (PHB p189):

The game organizes the chaos of combat into a cycle of rounds and turns. A round represents about 6 seconds in the game world. During a round, each participant in a battle takes a turn. ...
Once everyone has taken a turn, the fight continues to the next round if neither side has defeated the other.

In your example, the bugbear had a turn, either waiting for the party to arrive, or approaching them. If it knows about the combat, he is a part of it, for example its movement should be tracked in turn increments.

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    \$\begingroup\$ But "During a round, each participant in a battle takes a turn." sounds as if the Bugbear is not having a turn, as he is not "participant in a battle" yet? \$\endgroup\$ – ideamonster Feb 14 at 7:02
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    \$\begingroup\$ @ideamonster it had a turn, either waiting for the party to arrive, or approaching them \$\endgroup\$ – András Feb 14 at 7:05
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    \$\begingroup\$ @ideamonster here's a nice answer (to me) to anderstand the meaning of a combat/round/turn : rpg.stackexchange.com/a/140614/51851 \$\endgroup\$ – Zoma Feb 14 at 7:37
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    \$\begingroup\$ @ideamonster: Make sure you understand the mechanics of surprise, and how it occurs within the confines of initiative/rounds. \$\endgroup\$ – V2Blast Feb 14 at 8:21

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