Drop mixer speed to low and add vanilla extract, then blend for 30 seconds.
Keeping speed on low, quickly add dry ingredients to the wet. Tip: use a 1/3 or 1/2 measuring cup to continually scoop the dry ingredients in while the batter continues to mix (see above video for example). Continue to mix until dough begins to cling to the beater and has a soft and smooth texture, about 2-4 minutes.
Using a 1 tablespoon cookie scoop, scoop out dough and roll it between your hands. Place finished cookie ball on prepared baking sheet. Repeat this step until all dough is used, placing cookies about 2 inches apart on the baking sheet.
Use your thumb (or the back of a spoon) and press into the center of the cookie dough, creating a small well. See above video for example.
Bake cookies for about 12 to 15 minutes or until the sides of the cookies are puffed and bottoms of cookies begin to turn a light golden color.
Let cookies rest on the baking sheet for 5-10 minutes, then transfer to a wire cooling rack to cool completely.
Keeping speed on low, slowly beat in powdered sugar until fully incorporated. If you need to adjust the consistency, try add more milk or powdered sugar (1 tsp at a time) until texture is correct. Frosting should be a standard thickness.
Putting it all Together
Scoop 1 tablespoon of frosting in the well of each cookie. Place chopped fruit on top of frosting. Pour remaining frosting in a frosting bag (or in a ziplock bag with the corner cut) and drizzle more cream cheese frosting in decorative stripes across the top of the fruit as desired.
Allow frosting to dry completely before serving or storing. Cookies can be stored within air tight container in a cool place for up to 5 days.
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