Prepare the dough: Add the pitted Medjool dates, oat flour, almond butter, and dairy-free milk to a food processor. Blend until a soft, cohesive dough forms. If the mixture is too dry or crumbly, add more dairy-free milk, 1 teaspoon at a time, blending between additions. The dough should be soft and pliable but not overly sticky.

Roll out the dough: Place the dough between two sheets of parchment paper. Using a rolling pin, roll into a thin, even rectangle, approximately 1/4 inch thick. Carefully remove the top sheet of parchment paper.

Make the filling: In a medium bowl, combine the almond butter, pumpkin purée, maple syrup, cinnamon, pumpkin pie spice, vanilla extract, and oat flour. Mix until smooth, creamy, and spreadable.

Assemble the cinnamon rolls: Spread the pumpkin filling evenly across the date dough, leaving approximately 1/2 inch of space along one long edge. Starting at the opposite long edge, carefully roll the dough into a tight log. Use the parchment paper underneath to gently lift and guide the dough as you roll, peeling it away with each turn.

Freeze: Wrap the log tightly in parchment paper and place in the freezer for approximately 2 hours, or until firm enough to slice cleanly.

Slice and enjoy: Remove from the freezer and use a sharp knife to cut into 6 large or 8 medium cinnamon rolls. Allow to soften for 5–10 minutes before enjoying!