Yup.
Personally, my adjudicating surprise situations is strict:
- Unless there's an intentionally attempted ambush planned in advance by one side, and a clear case of the other side not expecting any danger, surprise automatically does not happen.
- If both of those are true, then surprise must be rolled for. The roll involved may be a variant from the usual Stealth vs Passive Perception, including involving adv or disadv or group checks etc, at my discretion.
- Attempting to surprise can never be automatically successful.