Jack in the Box Oreo Cookie Shake 3 cups vanilla ice cream 1 1/2 cups milk 8 Oreo cookies Combine the ice cream and milk in a blender and mix on low speed until smooth. Stir the shake with a spoon to mix, if necessary. Break Oreo cookies while adding them to the blender. Mix on low speed for 5 to 10 seconds or until cookies are mostly pureed into the shake, but a few larger pieces remain. Stir with a spoon if necessary to help combine cookies. Pour shake into two 12-ounce glasses.