To a large mixing bowl, add the whole wheat flour, all purpose flour, salt, and cinnamon. Stir until well combined.
Measure ⅓ cup coconut oil and transfer it to a heat-safe bowl. Microwave until completely melted, about 15-20 seconds. Add the melted coconut oil to the mixing bowl, along with the olive oil, pumpkin, sugar, and vanilla extract. Stir just until well combined.
Turn a mini muffin pan upside down. Scoop 1 heaping tablespoon of cookie dough and press the dough so that it completely covers the first muffin cup, creating an upside-down bowl shape.
Continue working, covering every other muffin cup with cookie dough (so that no two cookie bowls are touching).
Bake for about 14-16 minutes, or until the edges begin to turn lightly golden.
Allow the cookie cups to cool. Then carefully twist each cup to gently remove from the pan.
Immediately before serving, fill each pumpkin cookie cup with one small scoop of vanilla ice cream. Top with homemade salted caramel sauce.
Storage: cookie cups will keep for several days if stored in a covered, airtight container in a shaded, cool, dry location.