Start by placing the pumpkin purée in a saucepan over medium heat. Stir constantly until it thickens slightly and darkens in color. This step removes excess moisture and concentrates the pumpkin flavor.
In a mixing bowl, cream the softened butter with granulated and brown sugar. Mix until light and fluffy, which helps create soft cookies with even texture.
Mix in the egg yolk and vanilla extract until fully incorporated. The dough should look smooth and glossy at this stage.
In a separate bowl, whisk together flour, baking soda, salt, and pumpkin pie spice. This ensures the leavening and spices are evenly distributed.
Gradually add the dry ingredients to the wet mixture. Mix just until combined to avoid overworking the dough.
Stir in the cooled caramelized pumpkin and chocolate chips. The dough will be thick and slightly sticky.
Scoop dough onto a lined baking sheet and bake until the edges are set and centers look soft. Let them cool slightly before glazing.
Drizzle caramel glaze over cooled cookies. Allow it to set before serving for the best texture.