Heat air fryer to 350°F.
In a food processor, pulse pimento cheese until smooth. Transfer cheese to a piping bag fitted with a round tip; pipe cheese into each olive.
Pour flour into a shallow bowl. In another shallow bowl, whisk eggs. In a third shallow bowl, stir breadcrumbs and Parmesan.
Working one at a time, toss olives in flour, then dip into eggs, letting excess drip off. Toss in panko, gently pressing to adhere.
Back into eggs and panko for one more coating.
Place in air fryer for 5-7 minutes. Remove and let cool.