Q. 319: A bugbear with sweeping attack

If the new Bugbear were to act first in a combat and hit a target and elect to use sweeping attack, would the second target would take the ambush damage? I’d argue yes since the result of your attack roll determines whether or not you hit the creature.

J Craw also tweeted that effects that apply to ALL attacks, as opposed to just weapon attacks, can be applied to sweeping attacks.

https://twitter.com/JeremyECrawford/...2%2Fframe.html