Skip to Content

Chocolate Thumbprint Cookies with Cherries

Friends you will have to believe me when I tell you that these chocolate thumbprint cookies are going to be a family favorite for years to come! These simple Christmas cookies are full of chocolatey flavor, rolled in crushed almonds and then topped with cherry pie filling.

Can you believe we are already on our 3rd cookie recipe for our annual Christmas Baking Frenzy?! I have to say that these chocolate thumbprints may be my favorite ones yet – though the Frosted Sugar Cookie Bars and Chocolate Chip Shortbread Bars are so delicious in their own ways!

Red tablecloth lined with freshly baked Thumbprint cookies

Double Chocolate Thumbprint Cookies

I grew up on thumbprint cookies at Christmas thanks to my mom who is obsessed with the Classic Thimble Cookie – and I am not complaining since it has become a treasured cookie recipe for me year after year…BUT this year I wanted to step it up a bit and try something new!

If you love chocolate and cherries together you are going to love this recipe and I am sure of that! I began by melting some chocolate in a pot to add directly to the cookie batter- rather than just cocoa powder I knew it had to have that extra chocolate in it. Also, instead of just placing a maraschino cherry on top I decided that gooey cherry pie filling would add the texture I was looking for to go along with the crunchy almonds that crust the outside of the cookie. Are you drooling yet?

Chocolate thumbprints on cutting board with crumbled almonds being filled with cherry pie filling

FAQs For Thumbprint Cookies

Here are some of the questions you guys have asked about making thumbprint cookies over the years – if you have a question that isn’t here feel free to leave a comment or email us and we will respond as soon as we can!

How to Make Chocolate Thumbprint Cookies?

Thumbprint cookies are a relatively easy recipe to make though they do take a little bit of extra time because of the rolling and filling needed. Once you make your cookie dough create small 1″ balls and roll in crushed almonds (or any nut you prefer). Once you have rolled the dough balls in the nuts you then gently press an indent in the center of the cookie prior to baking which is where your filling of choice will go once they are cooled.

Can You Freeze Thumbprint Cookies?

Yes!! As with most of our cookie recipes you can definitely freeze them, meaning you can make them ahead of the busyness that comes with the Holiday season.

In order to freeze the thumbprint cookies you will want to first decide if you will freeze them prior to filling or not. We always freeze ours when they have already been filled and completed which simply requires a layer of parchment paper in between the layers to ensure there is no sticking. If you choose however to freeze your cookies before adding the filling you can go ahead and stack them without the parchment and they will be fine. With both scenarios you want to make sure you are using a tightly sealed container to keep them fresh.

How long will Thumbprint Cookies Stay Fresh?

Thumbprint cookies are pretty hardy little cookies – when I make them I always freeze them since they are for my Christmas baking and they last this way for 3 months (that’s the longest I’ve tried it). If you want to leave them in an airtight container on the counter I would say no longer than 1 week but use your judgement here. If you are using a fruit filling like we did I would suggest putting them in the fridge to keep them from developing any bacteria.

Be sure to PIN THIS RECIPE so you have it for later!

Chocolate Cherry Thumbprint cookies pin

More great Cookie Recipes

You May Need …

The following may contain affiliate links. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

There are two main ingredients you need to make these festive thumbprint cookies – Cherry Pie Filling and Roasted Almonds!

Recipe for Chocolate Thumbprint Cookies

Chocolate Thumbprint Cookie with Filling

These thumbprint cookies are simple, decadent and irresistibly festive with their red cherry centers!
Course Christmas Cookies, Cookies, Dessert
Cuisine American, English
Keyword Chocolate Thumbprint Cookies, Filled Cookies, Thumbprint Cookies
Prep Time 10 minutes
Cook Time 10 minutes
Filling 10 minutes
Total Time 30 minutes
Servings 3 Dozen
Author Melissa


  • Stand (or electric) mixer
  • Saucepan


  • ½ cup Semi-Sweet Chocolate Chips
  • 2 tbsp Shortening
  • ½ cup Butter – unsalted
  • ¾ cup Sugar
  • 1 Egg
  • 1 tbsp Milk we used 1%
  • 1 tsp Vanilla Extract
  • 2 cups Flour
  • 2 tbsp Cocoa Powder
  • 1 tsp Baking Powder
  • ¼ tsp Salt
  • ½ cup Finely Chopped Roasted Almonds
  • 1 can Cherry Pie Filling (with whole cherries)


  • Preheat oven to 350 °F and line baking sheet with parchment paper.
  • Add ½ cup of semi sweet chocolate chips along with the shortening to a small saucepan. Melt over low heat- stirring frequently. Remove from heat and allow to cool while you prepare the dough.
  • In stand mixer cream together butter and sugar on medium speed until fluffy. Add in cooled chocolate and beat to combine.
  • Add egg, milk and vanilla – beat on medium speed to fully combine.
  • In a medium bowl sift or whisk together your dry ingredients (flour, cocoa powder, baking powder and salt). Add to wet mixture and beat on low speed to just combine.
  • Shape dough into 1" balls and roll in chopped almonds. Place the balls approximately 1" apart on your prepared baking sheet and gently make an indentation in the center of each ball using your thumb.
  • Bake for 10-12 minutes, or until the edges are firm. Transfer to wire cooling rack and cool completely. You may need to use the back of a wooden spoon to gently press your indent again once they are removed from the oven.
  • Using a small spoon gently place a cherry in each indent – we added a small amount of pie filling as well to give it more texture while eating!

step-by-step making of thumbprint cookies

Melted chocolate in saucepan on grey kitchen towel

Begin by melting chocolate with shortening and allowing to cool while you make the dough.

Creamed butter and sugar in Kitchen Aid mixer bowl

Next, cream together sugar and butter on medium speed.

Creamy cookie dough batter in stainless bowl

Add in the cooled chocolate and mix. Add in egg, vanilla and milk and mix well.

Sift dry ingredients in medium bowl and add to wet -mix just to combine.

Cutting board with white bowl filled with crushed almonds for rolling chocolate thumbprint cookie balls

Shape dough into 1″ balls and roll in crushed almonds.

Thumbprint cookies on cutting board getting indent for filling

Gently use thumb for creating indent in center of each cookie. Bake in preheated oven 10-12 minutes before filling.

Almond crusted thumbprint cookies being filled with cherry pie filling

Once cooled, filled cookies with cherry pie filling and ENJOY!

Recipe Rating