Preheat the oven to 375 degrees F. Line a baking sheet with parchment, and spray the parchment with cooking spray.
Mix together the cream cheese and 2 tablespoons sugar in a small bowl. Roll each slice of bread flat with a rolling pin, and spread with 1 heaping teaspoon of the cream cheese mixture. Place 2 heaping teaspoons of the diced strawberries at one end of each slice. Starting at that end, roll up each slice. Pinch and press the seam and ends so each roll-up is sealed, and push back in any ingredients that may have snuck out of the ends.
Whisk the cream and eggs together in a small bowl. Combine the remaining 1/2 cup sugar and the cinnamon in a shallow dish. Dip each roll-up in the egg mixture until completely submerged, shake off excess egg, then cover completely in the cinnamon sugar. Arrange the roll-ups, seam-side down and evenly spaced, on the prepared baking sheet.
Bake the roll-ups until they're golden brown and the cinnamon sugar forms a crunchy layer, about 15 minutes. Let cool for 5 minutes, then transfer to a cutting board. Trim off any excess caramelized sugar, and slice each roll-up in half on the diagonal (be careful when slicing, as the filling is hot). Serve the roll-ups on a platter, with maple syrup on the side if using.
Never leave a child unattended in the kitchen. Limit the child to tasks that are safe and age-appropriate.
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