u/AdWilling9818

Is the assassin rogue feat Assassinate "In addition, any hit you score against a creature that is surprised is a critical hit." Considered as an 20 roll?

More precisely does the Boon of Irresistible Offense synergize with the assasin rogue?

Overwhelming Strike. When you roll a 20 on the d20 for an attack roll, you can deal extra damage to the target equal to the ability score increased by this feat. The extra damage’s type is the same as the attack’s type