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.
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.
While cookies cool, heat chocolate chips per package instructions, then transfer chocolate to a pastry bag or a ZipLoc bag with a corner cut (optional).
When ready to decorate, fill the well of each cookie with cherry pie filling (typically 2-3 cherries per cookie), then top each cookie with a drizzling of melted chocolate (optional).
Allow frosting to dry completely before serving or storing.
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