Preheat oven to 350°.
Coat 12 (6-ounce) custard cups with cooking spray.
Combine sugar and 1/4 cup water in a small, heavy saucepan; cook over medium-high heat, stirring gently as needed to dissolve sugar evenly. Continue cooking 4 minutes or until golden, stirring constantly. Immediately pour about 1 tablespoon sugar mixture into each of 12 prepared custard cups, tipping quickly until caramelized to coat the bottom of prepared cups.
Combine fat-free milk, vanilla, cinnamon, eggs, and condensed milk in a medium bowl, stirring with a whisk until well blended. Pour 1/2 cup milk mixture into each custard cup. Place cups in a jelly-roll pan; add hot water to pan to a depth of 1/4 inch. Bake at 350° for 35 minutes or until a knife inserted in the center comes out clean. Remove cups from pan; cool completely on a wire rack. Cover and chill at least 3 hours.
Loosen edges of custards with a knife or rubber spatula. Place a dessert plate, upside down, on top of each custard cup; invert custard onto each of 12 plates. Drizzle any remaining caramelized syrup over custards.