Prepare the chocolate pudding by whisking the pudding mix and cold milk together in a large bowl until smooth and thickened. Let it sit for about 5 minutes to fully set.

While the pudding sets, crush the Oreo cookies into fine crumbs using a food processor or by sealing them in a bag and crushing with a rolling pin.

To make the carrot strawberries, melt the orange candy melts in a microwave-safe bowl in 20–30 second intervals, stirring well between each, until smooth. Hold each strawberry by the leafy top and dip it into the melted orange chocolate, gently twisting to coat. Let the excess drip off, then place on parchment paper. If desired, drizzle a small amount of the remaining melted orange chocolate over the strawberries to create carrot-like texture lines. Allow the strawberries to set completely at room temperature or in the refrigerator.

To assemble the dirt cups, spoon a layer of chocolate pudding into each cup leaving space for the dirt layer. Add a generous layer of crushed Oreo crumbs.

Just before serving, gently press one chocolate carrot strawberry into the center of each cup. Tuck a small thyme sprig slightly behind or beside the strawberry so it looks like greenery sprouting from the soil.