Combine the flour, brown sugar, and cinnamon, then cut in the cold butter until the mixture turns crumbly, with no large butter lumps remaining. Refrigerate the crumble while you prepare the cookie dough.

Preheat the oven to 375°F. In a mixing bowl, beat the softened butter and brown sugar until smooth and slightly lighter in color, then beat in the blotted-dry pumpkin, egg yolk, and vanilla.

Fold in the dry ingredients until just combined, so the dough looks thick and cohesive with no dry streaks visible.

Scoop 2-tablespoon rounds of dough and place them on a sheet pan, leaving space between cookies. Press a generous pinch of the chilled crumble into the top of each cookie so it adheres.

Bake for 12–14 minutes at 375°F until the cookies are golden at the edges and the crumble looks set and lightly browned. Cool until warm, then drizzle with the cream cheese glaze.

Whisk powdered sugar, cream cheese, milk, and cinnamon until smooth and drizzle-ready, loosening with a little more milk if needed for a ribbon-like flow.