Trim the crusts from the bread. Flatten each slice with a rolling pin until about half its original thickness.
If using cream cheese, spread about 1/2 tablespoon thinly across each slice, leaving a 1/2-inch border on all sides.
Spread about 1 1/2 teaspoons of strawberry jam along one short end of each slice, keeping the border clear.
Roll each slice tightly from the filled end toward the empty end. Press the seam firmly to seal.
In a shallow dish, whisk the eggs, milk, vanilla, and 1/4 teaspoon of the cinnamon until fully combined.
On a plate, mix the granulated sugar with the remaining 1/4 teaspoon cinnamon, if using.
Dip each roll-up in the egg mixture for 2 to 3 seconds, turning to coat all sides and both ends. Let the excess drip off.
Roll each coated log in the cinnamon sugar, if using.
Preheat the air fryer to 375°F. Grease the basket or line it with perforated parchment.
Place the roll-ups seam side down in a single layer, leaving space between each one. Work in batches if needed.
Cook for 8 to 10 minutes, flipping at the 5 minute mark, until deep golden brown and firm.
Dust with powdered sugar and serve warm with fresh strawberries and syrup or extra jam for dipping.