Wash the strawberries thoroughly.
Remove the stems from the strawberries.
Roughly chop the strawberries into small pieces and set them aside.
Place the softened cream cheese in a small bowl.
If the cream cheese is too firm, microwave it for approximately 10 seconds to soften it.
Add the powdered sugar to the cream cheese.
Stir until the mixture is smooth and fully combined.
Trim the crusts from each slice of bread.
Using a rolling pin, flatten each slice of bread evenly.
Spread approximately 1 tsp of the cream cheese mixture along one edge of each flattened bread slice.
Place a small layer of chopped strawberries over the cream cheese mixture.
Starting from the filled edge, gently roll each bread slice into a tight roll.
Place the prepared roll ups seam-side down on a plate while preparing the remaining pieces.
In a shallow bowl, whisk together the eggs, milk, granulated sugar, and cinnamon.
If using vanilla extract, add it to the egg mixture and whisk until combined.
Preheat a nonstick skillet or pan over medium heat.
Lightly grease the pan with butter or cooking spray, if needed.
Carefully dip each roll up into the egg mixture, coating all sides.
Do not soak the roll ups for too long, as the bread may become too soft.
Place each roll up seam-side down in the preheated pan.
Cook until the seam is sealed and the first side is golden brown.
Gently rotate each roll about a quarter turn at a time.
Continue cooking until all sides are evenly browned.
Transfer the cooked roll ups to a serving dish.
Dust with powdered sugar.
Garnish with any remaining chopped strawberries.
Serve warm.