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Cookies:
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Whisk together the flour, baking soda, salt, and pumpkin pie spice.
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Working with a stand mixer, preferably fitted with a paddle attachment, or a hand mixer in a large bowl, beat the butter on medium speed until smooth and creamy. Add the brown sugar, molasses, and pumpkin puree and beat for 2 minutes. Add the egg and beat for 1 minute more.
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Reduce the mixer speed to low and add the dry ingredients, mixing until the flour and spices disappear. If flour remains in the bottom of the bowl, mix the last of the dry ingredients by hand to avoid over beating. You will have a very soft dough.
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Divide the dough in half and wrap each piece in plastic wrap. Freeze for at least 30 minutes, or refrigerate for at least 1 hour. The dough is sticky, so the longer time it can chill the easier it is to work with.
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Preheat oven to 350u00b0F. Line 2 baking sheets with parchment paper.
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Put the sugar in a small bowl. Working with one packet of dough at a time, divide it into 24 pieces (or use a small cookie scoop), and roll each piece into a ball. Roll the balls in the sugar, then place dough balls on prepared cookie sheets and use a the bottom of a glass to ever-so-gently press down on the cookies. Do not over crowd.
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Bake the cookies one sheet at a time for 7-9 minutes, or until the top feels set to the touch. Remove baking sheets from the oven. Let cookies cool 5 minutes on the sheets before transferring them to a cooling rack.
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Repeat with second batch of dough.
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Filling:
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In a medium bowl with an electric mixer, combine cream cheese and confectioners' sugar. Mix on low speed until the sugar is incorporated, increase speed to medium-high and mix for about one minute. Add in vanilla and continue mixing on low speed until vanilla in fully incorporated.
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To assemble the cookies, pipe or spread the filling on the bottom of one cookie. Top with another cookie and press together gently to create a sandwich cookie.
