In a large bowl, whisk together the flour, baking soda, salt, cinnamon, pumpkin pie spice, and oats. Set aside.
In a stand mixer or large bowl with a hand mixer, beat the butter, brown sugar, and granulated sugar on high speed for 2 minutes until creamy.
Add the vanilla, molasses, and eggs. Mix on medium speed until fully combined.
Gradually add the dry ingredients and mix on low speed until just incorporated.
Chill the dough in the refrigerator for 15 minutes. Meanwhile, preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
Scoop dough to make 36 cookies (about 1.5 tablespoons each). Place 12 cookies per sheet. Keep extra dough chilled between batches.
Bake for 8–9 minutes, or until cookies are just set. Allow to cool on the baking sheet for 4 minutes before transferring to a wire rack to cool completely.
For the frosting, beat the butter and marshmallow fluff on high speed for 3 minutes until light and fluffy.
Add powdered sugar, vanilla, and salt. Mix on low until combined, then beat on high for another 4 minutes until fluffy and smooth.
Once cookies are fully cooled, spread or pipe frosting on the flat side of one cookie, then top with another to make a sandwich.
Chill cookie sandwiches in the freezer for at least 10 minutes before serving. Store leftovers in the refrigerator if making ahead.