Apple Crisp Cookie Cups

Apple Crisp Cookie Cups - gluten free, vegan, and refined sugar free

A crispy oatmeal cookie cup filled with a sweet apple-cinnamon filling makes the perfect hand held treat. Full of fiber and wholesome ingredients, no one will know these cookies are actually good for you!

Apple Crisp Cookie Cups - gluten free, vegan, and refined sugar free

Anyone else obsessed with Shark Tank?

If you are, you might remember the inventors that brought a plastic sippy cup with a snack holder for a lid. They’re selling point was that it was great for those times when you need your other hand for something besides food. Or, in my opinion, the demoted hand not lucky enough to hold delicious goodies 😉 .

Well, these apple crisp cookie cups are kind of like that cup! (Yes, I had a point there…)

They’re like a hand held apple pie/oatmeal cookie hybrid that you don’t need a fork to eat. And, fits in the palm of your hand!

Apple Crisp Cookie Cups - gluten free, vegan, and refined sugar free

The cookie cup is a crispy oatmeal cookie with a hint of cinnamon that makes the perfect pairing to the sweet and creamy apple filling.

Simmering the apple filling brings out the apples’ natural sweetness, but if your sweet tooth is calling, you can also add a little extra sweetener to the mixture.

And trust me, cookie cups might look fancy, but they definitely aren’t hard to make. Although, if you want to trick your friends into thinking you spent hours on them, it will be our little secret.


Yields 10 cookie cups

Apple Crisp Cookie Cups

Gluten Free; Vegan; Refined Sugar Free; Soy Free; Egg Free; High Fiber

50 minPrep Time

12 minCook Time

1 hr, 2 Total Time

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    Cookie Cups
  • 12 dates, pitted
  • ¼ cup milk of choice
  • ½ tsp vanilla extract
  • 3 cups oat flour
  • 1 cup almond flour
  • 1 Tbsp + 1 tsp cinnamon
  • ¼ tsp allspice
  • 1/8 tsp salt
  • 2 Tbsp coconut oil
  • 1 Tbsp + 1 tsp molasses
  • 1 Tbsp + 1 tsp agave
  • Apple filling
  • 3 medium apples, chopped
  • ½ cup unsweetened applesauce
  • ¼ cup milk of choice
  • 1 Tbsp molasses
  • 1 tsp cinnamon
  • ½ tsp lemon juice
  • Pinch of salt
  • 2 Tbsp granulated sweetener of choice – optional


  1. For the cookie cups: preheat the oven to 350 F and spray a muffin tin with cooking spray.
  2. Combine the dates, milk, and vanilla extract in a food processor or blender. If the dates are dry, soak them in warm water for 30 min. to soften.
  3. In a medium sized bowl, combine the oat flour, almond flour, cinnamon, allspice, and salt. Whisk to combine.
  4. In a separate bowl, stir together the date paste, oil, molasses, and agave.
  5. Add the date mixture to the dry ingredients. Stir to combine until all the dry ingredients are incorporated. The mixture should feel like wet sand..
  6. Scoop the dough evenly into 10 cups of the muffin tin. Press the dough up the sides and on the bottom of the cups. You’ll have to use firm pressure to make sure the dough sticks together. I found it easiest to form the sides first and then fill in the bottom second.
  7. Bake in the preheated oven for 12 minutes or until the rim of the cookie cups turn a darker brown. Remove the tray from the oven and allow the cookie cups to cool completely in the tin. Once cooled, the cups will pop right out.
  8. For the filling: cut the apples (any kind will work, just pick a type you like. I used McIntosh.) into ½” cubes.
  9. In a medium sized sauce pan, add in the apples, applesauce, milk, molasses, cinnamon, lemon juice, salt, and optional sweetener if you want some extra sweetness.
  10. Turn the heat on high. Once the mixture begins to boil, turn the heat to low and simmer, covered, for 6 min. or until the apples soften. The mixture should have thickened slightly.
  11. Spoon the mixture evenly into the cooled cookie cups. If you don’t plan on serving them right away, you can transfer the cooled mixture into an airtight container and store in the refrigerator. The cups are very sturdy and will hold the filling without any problems, but if the mixture sits in the cups for a few hours, it will get the inside a tiny bit soggy.
  12. Enjoy your hand held apple crisp cookie cups and eat away!

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