Preheat the oven to 350F.
In a medium bowl, whisk together flour, pumpkin pie spice, baking powder, and salt.
In a large bowl, whisk together eggs, pumpkin puree, brown sugar, melted butter, and ¼ cup heavy cream. Add flour mixture to egg mixture and whisk until combined.
Drop dough in 1 tablespoon-sized mounds (or use a cookie scoop), onto a parchment or silicone lined baking sheet. Aim for 12 per sheet! Bake until tops of cookies spring back when gently pressed, 10-12 minutes. Rotate sheets halfway through. Transfer to wire racks to let cool completely.
In a medium bowl, using an electric mixer, beat the room temperature butter for the filling until whipped and creamy. Add in the cream, cocoa powder, and powdered sugar, and beat on medium high until fluffy, about 2 minutes. Scrape the bottom and sides often if using a stand mixer.
Scoop filling into a large Ziploc bag, cut a small hole in a corner, and pipe on the underside of half the cookies, then top with remaining cookies. When ready to serve, dust with additional powdered sugar. Enjoy!