Cherry Pie Shortbread Thumbprint Cookies

One of my favorite parts of the holiday season was always the vast assortment of cookies available. Monster oatmeal and chocolate chip were the everyday cookies, but the really fancy and exotic treats only were brought out of the family recipe collection for the holidays.

There were a few years I remember my Mom went wild in the kitchen and we had so many exciting cookies and caramel corn treats. Now I try to pace myself and am always looking for a great cookie recipe to use for either a holiday cookie exchange, a homemade gift or that freezes well till needed. These Cherry Pie Shortbread Thumbprints fit into all of those categories, though I am most excited about freezing a bunch to make closer to Christmas.

These are super easy to make, take just a few ingredients, but are a truly "Wow" cookie. Flaky and buttery with just a hint of cherry pie.

My husband is very vocal about not liking Cherry pie. That did not stop him from inhaling his fair share of these tender little cookies. He claimed they were the perfect ratio of filling (about one cherry each) to buttery cookie "crust".

Now, don't be alarmed if the cookie dough seems a little "craggy" or dry. Just press it into a ball, press in a little indent and then smooth out the edges the best you can. I used a small cookie scoop to keep my balls as uniform as possible.

If needed, a couple drops of water can help to hold the dough together. But trust me, dry is just fine.

Now, if you happen to have a little homemade cherry pie filling on hand, I would use that. Sadly, I never had a chance to can or freeze pie cherries this year. Let's say it is at the top of my list for next year.

But, if you happen to be all out of homemade, go grab a can of pie filling. It works just fine!

My little thumbprints held one cherry and a little filling. Again, my husband swore this was perfection.

Bake these little beauties for about 15 minutes, then let them cool and set up for another 15 minutes. Then they can be iced and are ready to enjoy.

And if you want to stock up on cookies for the holidays, just roll and indent the cookies, then freeze. When ready thaw and bake as usual.

Cherry Pie Shortbread Thumbprints

You Will Need:

• 1 c. unsalted butter, softened
• 1/2 c. sugar
• 2 c. all-purpose flour
• 1 tsp. vanilla bean paste
• 1 tsp. salt
• 1 can cherry pie filling
• 4 Tbsp. powdered sugar + more if needed
• 1 Tbsp. milk

Preheat the oven to 375 degrees.

In a stand mixer, cream together the butter and sugar. Add in the vanilla bean paste and salt. Slowly add in the flour, making sure to scrape down the sides. Dough may seem dry, but will hold together when pressed firmly.

Use a small cookie scoop to form balls. Indent the top to hold filling. Spoon a little into each cookie well. 

Bake for 15 minutes. The cookie edges should be starting to turn light brown. Remove from the oven and let them set for another 15 minutes. 

In a small bowl, whisk together the powdered sugar and milk. It should be thick. Add additional sugar as necessary. Put into a zip-top bag and cut the corner to pipe over the cookies. Allow the sugar to set up for another few minutes before serving.

Enjoy!