Preheat oven to 350°F.
Line two baking sheets with parchment paper or spray with non-stick cooking spray. Set aside
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and sugar until creamy.
Beat in the pumpkin puree and vanilla extract and then the eggs, one at a time, until mixture is well combined.
With mixer turned off, add the pumpkin pie spice, flour, baking powder and salt. Mix on low speed until a thick dough forms.
Lightly flour a clean countertop or large cutting board.
Turn out your dough onto the floured surface. Using a sharp knife or bench scraper, cut the dough in half (does not have to be exact). Set one half aside.
Using a lightly floured rolling pin, gently roll one half of dough to ¼-inch thickness.
Use a pumpkin-shaped cookie cutter to cut out pumpkin shapes.
Using a floured spatula, carefully lift each pumpkin onto prepared baking sheet, placing them 2 inches apart.
Repeat with remaining dough until all dough has been used up.
Gently press scraps of dough together and re-roll to cut out more shapes.
Bake for 7-9 minutes, rotating cookie sheets halfway through, or until cookies are just starting to turn golden brown around the edges.
Let cool on baking sheets for 5 minutes before transferring to a wire rack to cool completely.
Fill a medium saucepan with about 2 inches of water and place over low heat.
Place chopped chocolate in a heat-proof bowl (I use a glass Pyrex bowl for this) and set over the water.
Be sure the water is not touching the bottom of the bowl. Let the chocolate warm and slowly melt over the hot water, uncovered, until it is completely melted, gently stirring with a heat-resistant rubber spatula.
Do not allow any water to splash or touch the chocolate or it will cause the chocolate to seize and become unusable.
Remove melted chocolate from heat and gently dip one side of each cooled cookie into the chocolate.
Place dipped cookies onto a wire rack set over a piece of parchment paper or baking tray to catch any drips.
Sprinkle with decorations while chocolate is warm, if desired.
Allow to cool completely or place in the refrigerator to allow chocolate to set.