Peanut Butter Stuffed Chocolate Jack-O’-Lantern Cookies

1. Preheat oven to 350 degrees. In a large mixing bowl, cream together the butter, sugar, and vanilla until light and fluffy, about 3-5 minutes. Add the egg and mix until evenly combined. Add the flour, 1/2 cup cocoa powder, baking soda, and salt, beat until combined and the dough forms a ball. If your dough feels too wet to roll out, add the additional 2 tablespoons cocoa powder.
2. Generously flour your work surface. Divide the dough in half and flatten each half into a disk. Roll out the dough to 1/4 inch thickness. Make sure you're using enough flour or your dough will stick. Cut out the cookies using a pumpkin cookie cutter or pumpkin cookie stamp. Carefully transfer the cookies to a parchment-lined baking sheet. Cover the baking sheet and place the sheet in the freezer, freeze until firm, about 10 minutes. Roll out the leftover scraps, and repeat with the remaining disk of dough.
3. Bake the cookies for 10-12 minutes. Cool on the baking sheet five minutes and then transfer to a wire cooling rack to cool completely.
4. To make the filling. Add the peanut butter, butter, powdered sugar, and vanilla to the bowl of a stand mixer. Beat until light and fluffy.
5. Dip half of the cookies, stem side down, into melted chocolate to coat about 1/3 of the top (see photos). Decorate as desired with additional melted chocolate. Sprinkle with sea salt. Chill the cookies in the freezer for 10 minutes. Spread the peanut butter filling over the cookie halves with no chocolate. Place the top cookie, chocolate side up over the peanut butter, gently pressing to adhere. Cookies can be served immediately or stored in an airtight container for up to 3 days.