In a mixing bowl, whisk together the chocolate pudding mix and cold milk for 2 minutes. Let it sit for 5 minutes to thicken.
Melt the white chocolate wafers in a microwave-safe bowl in 30-second intervals, stirring in between until smooth.
Stir in orange food coloring to achieve a carrot-like shade.
Holding each strawberry by the stem, dip it into the melted orange chocolate, ensuring full coverage. Place on parchment paper to set.
Once set, drizzle extra melted chocolate over the strawberries for a realistic carrot texture.
Spoon the pudding into serving cups, filling each about three-quarters full.
Sprinkle crushed Oreo cookies over the pudding to create the "dirt" layer.
Press two chocolate-dipped strawberries into each cup to resemble carrots in soil.
Serve immediately or refrigerate until ready to enjoy.