In the bowl of a stand mixer fitted with a paddle attachment, cream together the cream cheese and orange extract until smooth and fully combined.
Add 2 cups of the powdered sugar and the milk. Mix on medium speed until creamy.
Add the remaining powdered sugar and mix on low until the dough forms and begins to pull away from the sides of the bowl. It should be soft, smooth, and easy to roll.
Roll the mixture into small balls, about 1 inch in size. If the dough feels sticky, chill it for 10 minutes or dust your hands with powdered sugar to help shape the candies easily.
Place the rolled balls on a parchment-lined baking sheet and refrigerate for 30 minutes so they firm up.
After chilling, use the back of a fork to gently press each piece to about 1/4-inch thickness, creating a ridged pattern on top.
In a small microwave-safe bowl, melt the dark chocolate in 15-second increments, stirring between each interval until smooth.
Dip each cream halfway into the chocolate and place it back onto the parchment-lined sheet.
Refrigerate for about one hour to allow the chocolate to fully harden. Store in an airtight container in the refrigerator for up to a week, or freeze them for longer storage.