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.
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Jack-In-The-Box Oreo Cookie Shake (cont.)