D&D 5E question about surprise

I'd totally allow surprise in a social situation, esp if it involves the level of deception of a doppleganger assassin.
I'd probably use Insight vs Deception (or Deception vs Passive Insight) instead of Stealth and Perception if I felt it was relevant.

Generally two groups meeting the wilderness are too suspicious, if not outright hostile.
Attacking in the middle of a shared meal several hours later might well be sufficiently unexpected.

As for kicking down a door, mostly it's a case of whether the players have been successfully stealthy and if the monsters have been recently alerted to a threat. Even those on guard duty are likely to get bored and their attention waver.

Of course more suspicious/alerted individuals might not be surprised even if their compatriots are.
(An adventurer tailing the doppleganger assassin in the midst of a court party)
 
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For a "surprise" attack in a social situation, I simply grant advantage to the attack roll if I feel it's warranted. Technical surprise is too strong IMO.
 

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