Preheat the oven to 350°F. Line three 6-inch cake pans with parchment paper.
To make the batter: In the bowl of a stand mixer fitted with the paddle attachment, add the butter, cane sugar and vanilla extract.
Mix on low until combined and there are no butter chunks.
Add the pumpkin puree, milk, all purpose flour, baking powder, pumpkin spice, and salt. Mix on low until combined into a smooth cake batter. Be sure to scrape down the sides of the bowl part way through mixing, this will ensure everything mixes together evenly.
Add in the chocolate chips and mix to combine completely.
Transfer the cake batter to the prepared baking pans. It’s best to weigh them so they are even since this is a naked cake design. They will weigh about 270 grams each. Spread out the batter evenly.
Bake at 350°F for 20 minutes or until a toothpick inserted in the center comes out clean. Let the cakes cool completely in the cake pans before removing.
To make the decorating frosting: In the bowl of a stand mixer fitted with the paddle attachment, add the shortening, powdered sugar and milk.
Mix on low until combined, then speed the mixer up to high and whip for 2 to 3 minutes, or until light and fluffy. Be sure to scrape down the sides of the bowl part way through mixing to ensure the frosting is smooth and everything is mixed well.
Transfer a small amount of frosting, only a few tablespoons, to a piping bag with Ateco tip #4. This is going to be the writing for the RIP so we don’t need a lot of frosting here, you can just eyeball this.
Transfer the remaining bulk of the frosting into a piping bag with Ateco tip #808, this is for the ghosts. Set aside the piping bags.
To make the black frosting: No need to wash the mixing bowl, add in the butter, powdered sugar, vanilla extract and milk.
Mix on low until combined and then speed mixer up to high and whip for 2 to 4 minutes or until light and fluffy. Be sure to scrape down the sides of the bowl part way through mixing to ensure you have a smooth and creamy frosting.
Transfer the frosting to a piping bag with Ateco tip #827.
To make the headstones: Using the white frosting with Ateco tip #4, pipe RIP onto the top of the mini chocolate bars. You can make as many headstones as you like, but I think about 5 to 7 fit nicely on the cake.
To assemble the cake: Place a small dollop of frosting on your cake plate or cake stand. Then add the first cake layer, bottom side down as this helps ensure the cake is flush with the cake stand so it sits flat.
Starting at the edge of the cake, pipe a spiral using the black frosting and work your way into the center of the cake.
Top with the second cake layer, but put this one bottom side up as this helps ensure the cake looks straight. Then, pipe another spiral of buttercream frosting, starting at the outer edge and working your way into the center.
Top with the third cake layer, bottom side up again. And, finish with the last spiral of black frosting.
Crumble up the chocolate cookies into the center of the cake to look like dirt.
Place the headstones anywhere you want on top of the cake with the RIP part on the top.
Pipe small dollops of frosting using the white frosting with Ateco tip #808 to create ghosts (watch the video, it helps!).
Last, transfer a small amount of leftover black frosting into a piping bag with Ateco tip #2. Pipe eyes and a mouth by just piping a small circle onto the ghosts.
Store under a cake dome until ready to serve.