Dry out the pumpkin. Spread the pumpkin on a double layer of paper towels in a bowl or on a plate. Press another paper towel on top to soak up the liquid. Swap in fresh towels and keep pressing until the pumpkin is thick and pasty and you're left with about 1/2 cup (113g).
Mix the dry ingredients. Whisk the flour, baking soda, pumpkin pie spice, cinnamon, and salt in a medium bowl.
Mix the wet ingredients. In a large bowl, whisk the cooled melted butter with both sugars and the maple syrup. Add the egg yolk and vanilla, whisk until smooth, then whisk in the blotted pumpkin.
Make the dough. Add the flour mixture to the wet ingredients and fold with a spatula just until no flour streaks remain. The dough will be soft and sticky, which is exactly right.
Chill. Cover the bowl and refrigerate for at least 2 hours, or up to 3 days. Don't skip this. Warm dough spreads into thin, flat cookies.
Make the crumb topping. Whisk the flour, brown sugar, and pumpkin pie spice in a small bowl. Work in the softened butter with a fork or your fingertips until it looks like damp sand with small clumps. Keep it in the fridge or freezer until you're ready to bake.
Get ready to bake. Heat the oven to 350°F (177°C) and line two baking sheets with parchment or silicone mats.
Shape and top. Roll the cold dough into balls of about 1 1/2 tablespoons (35g) each and space them 3 inches apart. Press your thumb into the tops a few times to form a shallow dip, then pile on a generous spoonful of the cold crumb topping.
Bake. Bake for 14–15 minutes, until the edges are set and just starting to turn golden. Let the cookies rest on the pan for 10 minutes before moving them to a wire rack.
Make the icing. In a small saucepan over low heat, warm the butter and maple syrup, stirring now and then, until the butter melts. Take it off the heat, whisk in the powdered sugar until smooth, and add a pinch of salt to taste.
Drizzle. Drizzle the warm icing over the cooled cookies. It firms up in about an hour.