Preheat oven to 350°. Spray a 13x9-inch baking pan with baking spray with flour.
In a large bowl, beat cake mix, milk, eggs, and oil with a mixer at low speed until moistened, about 30 seconds. Increase mixer speed to medium, and beat for 2 minutes. Pour into prepared pan.
Bake until a wooden pick inserted in center comes out clean, 20 to 25 minutes. Using the end of a wooden spoon, poke holes all over cake.
In a medium microwave-safe bowl, whisk together dulce de leche and 1⁄2 cup cream. Heat at high until dulce de leche is smooth and fluid, about 30 seconds. Pour evenly over warm cake, allowing it to soak in completely, spreading with a spatula as needed. Refrigerate for at least 3 hours or up to overnight.
In another large bowl, beat cream cheese and condensed milk with a mixer at high speed until smooth, stopping to scrape sides of bowl. Add confectioners’ sugar, and beat at low speed until combined, stopping to scrape sides of bowl. Add remaining 1 1⁄4 cups cream, 2 tablespoons at a time, beating until combined after each addition. Beat at a high speed until soft peaks form. Immediately spread over chilled cake. Top cake with Grilled Pineapple Rings as desired. Serve chilled.
Recipe by Paula Deen Magazine at https://pauladeenmagazine.com/pineapple-poke-cake/