Preheat oven to 350°F and prepare two 9-inch round cake pans with parchment paper and nonstick spray.
Whisk together flour, sugar, cocoa powder, baking soda, baking powder, and salt in a large mixing bowl.
Whisk eggs, milk, vanilla extract, and vegetable oil together until slightly foamy.
Pour the wet ingredients into the dry ingredients and stir until just combined.
Divide the batter evenly between the prepared cake pans and smooth the tops.
Bake for 28–32 minutes until a toothpick inserted into the center comes out with a few moist crumbs.
Cool cakes in the pans for 15 minutes before transferring to wire racks to cool completely.
Break the cooled cake into chunks and pulse in a food processor until fine crumbs form.
Transfer the cake crumbs to a large mixing bowl.
Beat shortening, butter, powdered sugar, and milk together until fluffy and pale.
Add the frosting to the cake crumbs in three additions, folding gently after each addition.
Knead the mixture gently with your hands until fully combined and uniform.
Line a baking sheet with parchment paper.
Scoop the mixture into equal portions using a cookie scoop.
Roll each portion into a smooth ball using your hands.
Place the cake balls on the prepared baking sheet with space between each.
Freeze the cake balls for 2 hours until firm.
Melt chocolate chips and coconut oil together in a microwave-safe bowl until smooth.
Allow the melted chocolate to cool slightly before dipping.
Insert a lollipop stick halfway into each chilled cake ball.
Dip each cake pop into the melted chocolate until coated.
Tap the sticks gently against the bowl to remove excess chocolate.
Place the dipped cake pops upright on a parchment-lined baking sheet.
Allow the chocolate coating to set completely before serving.