Is there something off the screenshot that shows critical failure, instead of just a failure? This image shows a DC of 10, with a Roll of 1. Since no bonuses to the skill check are shown in this screenshot, a roll of 1 to 9 would be a fail.
It never even applies modifiers when rolls natural 1. Also no, for that roll in particular the very minimum Astarion could roll is 10. Specifically 1 + 5(dexterity) + 3(proficiency) +1(guidance).
