Preheat the oven to 350 degrees F. Beat the butter, pumpkin puree, vanilla, and coconut sugar until well combined. In a separate bowl, whisk together the oat flour, pumpkin pie spice, cinnamon, baking soda, and salt, and then slowly add it to the butter mixture, beating on low, until well combined and a cookie dough forms.

Turn the beater off and stir in the milk and oats. Using a cookie scoop (I used a D24, approximately 2 tablespoons), scoop the cookie dough and roll between your hands to create a ball. Place each cookie dough ball about 2 inches apart on a baking sheet lined with parchment paper.

Next, press down in the center of each cookie dough ball with the back of a round measuring spoon or your thumb and bake for 10-12 minutes (10 minutes for softer cookies). Remove from the oven and allow them to cool completely.

While the cookies are cooling, make the date caramel. Pit the dates and add them to a microwave safe bowl/measuring cup. Cover with water and microwave for 2 minutes. Drain and add to a food processor or high speed blender. Add the vanilla and coconut cream and blend until til smooth, stopping to scrape down the sides, until creamy. Set aside.

Once the cookies are completely cool, gently spoon some of the date caramel into the middle of each cookie. Store leftover cookies covered on your counter for up to 3 days.