Chocolate Pudding

1. Whisk the sugar, cornstarch, cocoa powder, and salt together in a 2.5 quart saucepan.
2. Cook on low heat, gradually streaming in the milk a little at a time and ensuring that the cornstarch does not clump. Continue to cook over low medium heat, whisking occasionally and scraping the sides of the pot as the mixture continues to warm.
3. Meanwhile, in a medium heatproof bowl, whisk together the heavy cream and egg yolks.
4. Once the cocoa mixture on the stove has started to bubble a little, prepare to temper the heavy cream and egg mixture. While constantly whisking the heavy cream mixture, carefully pour in a little of the hot milk mixture to temper it for a few seconds.
5. Pour all of the mixture back into the saucepan and continue to cook over medium high heat, whisking constantly until the pudding thickens and begins to boil up like hot lava. Be sure to scrape the sides of the pot and keep a close eye on the pudding.
6. Remove the pudding from the heat and whisk in the chocolate and vanilla extract.
7. Transfer pudding to a large heat safe bowl and cover with plastic wrap by placing the plastic wrap directly on the surface of the pudding to avoid a skin from forming. Chill for at least two hours.

Chocolate Cookies

1. Preheat oven to 350º F.
2. Whisk the flour, cocoa powder, baking soda, and salt together in a large bowl and set aside.
3. In a stand mixer fitted with a paddle attachment, cream together the butter, sugar, and melted chocolate on medium speed until light and fluffy. Scrape down the sides of the bowl.
4. Add eggs one at a time, followed by the vanilla extract.
5. With the mixer on low, slowly add the flour mixture and mix until smooth, scraping down the sides of the bowl as needed.
6. Using a 2 tablespoon scoop, form cookies into balls and place each cookie a few inches apart on a parchment lined cookie sheet. If the dough becomes difficult to work with, pop the bowl in the fridge to chill for 5-10 minutes.
7. Bake for 10-11 minutes or until cookies are firm around the edges. Let the cookies cool for about 10 minutes on the baking sheet before carefully moving them to a cooling rack.

Assembly

1. Transfer chilled pudding to a piping bag with a large round piping tip.
2. Pipe a circle of pudding on each cookie, being careful to leave a small border of cookie free. Use an offset spatula to spread the pudding so it is level.
3. Top each cookie with finely crushed oreos and two pumpkins. Chill until ready to eat. Enjoy!