In a medium bowl, combine the sliced strawberries and granulated sugar. Toss to coat and let sit for about 10 minutes to release their juices.
In another bowl, mix the softened cream cheese, powdered sugar, and vanilla extract until smooth and creamy.
Spread a generous layer of the cream cheese mixture on four slices of bread. Top with the sugared strawberries, then place the remaining slices of bread on top to create sandwiches.
In a shallow dish, whisk together the flour, baking powder, salt, and cinnamon. In another bowl, whisk together the egg and milk until well combined.
Heat about 2 inches of vegetable oil in a deep skillet or pot over medium heat until it reaches 350°F.
Dip each sandwich into the egg mixture, allowing any excess to drip off, then coat with the flour mixture, pressing gently to adhere.
Carefully place the coated sandwiches in the hot oil, frying in batches if necessary, until golden brown on both sides, about 2-3 minutes per side. Remove and drain on paper towels.
Serve warm, optionally topped with whipped cream.