In a small microwave safe bowl, combine the white chocolate chips and vegetable oil. Microwave in 30 second intervals, stirring in between, until melted and smooth.
Drop in the orange food coloring to reach your desired shade of orange, then stir again to combine.
Working with one strawberry at a time, hold each washed and dried strawberry by the leaves, lifting them up so they don’t get covered, and dip to coat in the melted chocolate.
Shake or tap off any excess melted chocolate back into the bowl, then place on a baking sheet lined with parchment paper or a silicone baking mat, and repeat with the remaining strawberries.
Transfer the remaining melted chocolate into a ziploc bag, cut off one end, and drizzle over the strawberries to make horizontal lines, then place the dipped strawberries in the fridge to set.
In a large mixing bowl, combine cold milk and instant chocolate pudding mix. Whisk to get out any lumps, then set aside to thicken for 5 minutes.
In the meantime, combine heavy whipping cream and powdered sugar in a separate bowl. Whip to form stiff peaks, then gently fold the whipped cream into the thickened pudding. Set aside.
Add your Oreo cookies to the bowl of a food processor and pulse to crush the cookies into tiny crumbs. You can also crush them with a Ziploc bag and rolling pin if you don’t have a food processor.
Grab your cups of choice, then begin layering the Oreo crumbs with the pudding mixture. You’ll start with Oreos on the bottom, then pudding, repeat one more time, and top with more Oreo crumbs. You’ll end up with 5 layers in each cup.
When you’re done layering, top each pudding cup with two “carrot” strawberries and refrigerate until ready to enjoy!