For the Sugar Cookies: Beat the softened butter, granulated cane sugar, and brown sugar for 2 minutes on high speed. Add in the eggs and beat for 1 more minute, until smooth and creamy. Stir in the vanilla extract.
In a large bowl, mix the flour, pumpkin pie spice, baking powder, and salt together. Add into the egg mixture and fold together just until combined.
Press into a large rectangle, tightly cover with saran wrap, and refrigerate for 1-2 hours.
Preheat oven to 400F. Line two large cookie sheets with parchment paper.
Lightly flour a clean surface. Roll out the chilled cookie dough to 1/8” thick. Using pumpkin-shaped cookie cutters, cut out an equal amount of cookies. Transfer to the prepared cookie sheets.
To create the jack o’lanterns, carefully use a small sharp knife to cut out the faces of a jack o’lantern on half of the cookies.
Bake for 6-8 minutes, until lightly golden on the edges. Let cool completely while you make the ganache filling.
For the Chocolate Ganache: Chop the chocolate into small chunks and place into a bowl. Heat up the heavy cream until steaming but not boiling. Pour over the chocolate chunks and leave uncovered for 10 minutes. The chocolate should be melted and smooth when you stir it all together. Cool uncovered for 20-30 minutes before transferring to a piping bag.
To Assemble the Jack O’Lanterns: Pipe a small amount of chocolate ganache on the regular pumpkin cookies, spreading out an even layer with an offset spatula. Add a jack o’lantern cookie on top and gently press down. Repeat with remaining cookies. (Optional: Dust with powdered sugar or orange icing.) Enjoy!
PLEASE NOTE: Placing orders by December 14th will give you the best chance of receiving your order by December 24th. Personalized orders can take even longer, so plan ahead and order ASAP!