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Step 1
Preheat the oven to 350°F. Grease two regular-size (12 cup) muffin tins with nonstick cooking spray.
Step 2
Roll each sugar cookie into a ball and place into the muffin tin. Using a tart shaper dipped in flour, or the back of a spoon, gently press the dough into the pan and onto the sides. Make sure the bottom isn't too thin and keep the sides higher than the bottom to create an edge on the crust.
Step 3
Once all muffin tins are full, bake for 4 minutes. The crust will not be fully cooked. Remove from the oven.
Step 4
Slice the peaches into smaller pieces. This can be done easily with a spoon on a plate. Spoon a small amount of filling into each cookie cup and return to the oven. Bake for 6-8 minutes or until the crust is golden brown. Remove from the oven and let them cool before removing the cookie cups from the pan.
Step 5
Whisk together powdered sugar, milk, and vanilla until smooth. Transfer the icing to a resealable sandwich bag and seal shut. Snip the tip of the bag with scissors and drizzle on top of each peach pie cookie.
Step 6
Serve immediately or cover and refrigerate until ready to serve.