Love and Olive Oil
Gingerbread Thumbprint Cookies

Gingerbread Thumbprint Cookies

Gingerbread Chocolate Thumbprint Cookies


Only 10 more days until Christmas!

And that means I’ve only got 9 more days to post gingerbread recipes.

I’m going ALL IN… 2016 is officially the year of gingerbread (because I think we all deserve something sweet after a year like this one).

Gingerbread Chocolate Thumbprint Cookies

Taylor recently told me he doesn’t really like gingerbread… and just like that I’m questioning our 15 year relationship.

Just kidding. That just means more cookies for me!

These cookies, though… I think the combination of gingerbread and chocolate is an undiscovered secret, because even gingerbread-hating husbands will devour these in no time flat.

Gingerbread Chocolate Thumbprint Cookies

The filling, while it looks like a slightly melted chocolate kiss, is actually a mix of melted chocolate, butter and a bit of corn syrup. This makes the chocolate set up nicely (it won’t smudge if a few cookies are bagged together), but it’s still soft enough to bite through. After spooning the filling into 1 or 2 cookies, I realized that piping it in was so much easier. Hence the little kiss-like tip on the top of each one.

Now that I think of it, seeing how well the gingerbread-and-raspberry combination worked, you could also fill these with a raspberry jam which would be entirely lovely. But the chocolate is nice too… Ooh! How about a Chocolate raspberry jam? Boom. Brilliant.

Now if you’ll please excuse me I have to go gingerbread ALL THE THINGS. Let’s see how many more gingerbread recipes I can post between now and Christmas, shall we?

Gingerbread Chocolate Thumbprint Cookies

Gingerbread Thumbprint Cookies

Soft, chewy gingerbread thumbprint cookies rolled in sugar and filled with smooth, rich dark chocolate. Even if you don’t love gingerbread you’ll devour these!

Did you make this recipe?


For Gingerbread:

  • 3 cups (12.75 ounces) all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon kosher salt
  • 2 teaspoons ground ginger
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon ground allspice
  • 1/4 teaspoon ground nutmeg
  • 4 tablespoons unsalted butter, room temperature
  • 6 tablespoons unflavored vegetable shortening, room temperature
  • 3/4 cup packed brown sugar
  • 1/2 cup unsulphured molasses
  • 1 large egg
  • 1 teaspoon vanilla extract
  • granulated sugar, for rolling

For Filling:

  • 10 ounces dark or semisweet chocolate, finely chopped (1 cup)
  • 1 tablespoon butter
  • 1 tablespoon corn syrup


  1. In a bowl, whisk together flour, salt, baking soda and spices; set aside.
  2. In a large mixing bowl or the bowl of a stand mixer, beat butter and shortening together until smooth. Add sugar and beat 1 to 2 minutes or until fluffy. Beat in molasses. Scrape down the sides of the bowl, then add egg and vanilla and mix until smooth.
  3. Add half of dry ingredients and mix on low speed until just incorporated, scraping down the sides of the bowl as needed. Add remaining dry ingredients in two additions until no streaks of flour remain. The dough should be thick and just slightly sticky.
  4. Cover bowl with plastic wrap; chill for at least 1 hour or overnight.
  5. Preheat oven to 350 degrees F. Line a cookie sheet with parchment paper or a silicone baking mat.
  6. Roll dough into 1 inch balls (or use a small cookie scoop which is the perfect size). Roll into a smooth ball, then roll in granulated sugar. Arrange on prepared baking sheet, leaving 2 inches of space between balls.
  7. Gently press an indentation into each cookie using your thumb or the back of a rounded 1/4 teaspoon (something like a melon baller, or even a marble would also work well). Don’t press all the way, you want the indentation about half the depth of the cookie without it cracking too much around the edges.
  8. Bake for 7 to 9 minutes or until puffed and bottoms are just barely starting to darken; bake them on the lower side of the time range if you will be shipping your cookies or if you prefer softer cookies overall.
  9. Re-press the puffed indentations while the cookies are still warm, then let cool for 10 minutes before transferring to a wire rack to cool completely. Repeat with remaining dough.
  10. To make filling, gently melt chocolate together with butter and corn syrup in a saucepan over the lowest heat setting possible, or in the microwave on 50% power in 30 second intervals.
  11. When chocolate is melted and smooth, transfer to a piping bag fitted with a 1/2-inch-round tip, then pipe into thumbprints. You can also spoon the chocolate into the thumbprints, but I found the piping bag way more efficient. Let sit at room temperature for about 1 hour or refrigerate briefly until chocolate is set.
  12. Cookies will keep in an airtight container for up to 5 days.
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  1. These turned out great. Instead of the filling, I pushed a white chocolate peppermint kiss candy in them as soon as I took them out of the oven. A soft, spiced cookie with a sweet top. Perfect! As an added holiday touch, I turned the kisses upside down and put them in the cookies. That left the cookie with a white chocolate top with red and green specs in it.

  2. These look amazing and am def going to add them to my Christmas cookies. Can you please tell me, if I wanted to make a white chocolate version of the filling how it can be done??

    Thanks for this absolutely delicious recipe!!

    • You should be able to sub white chocolate here no problem! It’ll be a bit softer than dark chocolate but should be very tasty!

  3. I just made them for Orthodox Christmas and they are amazing! I’m convinced that they are going to be the star among all other cookies! Thanks for sharing the recipe. I tagged you on instagram if you’d like to see how they turned out :)

  4. This recipe keeps coming back to me on Pinterest, need to make it.

  5. thank you this looks wonderful, and also have gingerbread haters, or at least dis-likers that I have to address, and chocolate might do the trick!

  6. These are delicious. I used white chocolate chips for the filling instead of the dark chocolate, but had to also add some heavy cream to make it fluid. Filled them with a spoon. Thank you so much for the recipe. I will definitely be making these again.

  7. These look amazing, Lindsay – can’t wait to give them a try!

  8. Can the dough be chilled longer than overnight?

    • I’d say 2-3 days would be the absolute max. Longer than that and I’d suggest rolling and shaping the dough into thumbprints and freezing it like that. Then you can bake the cookies fresh right from frozen (add about 2 minutes to the cook time).

    • I ended up refrigerating for 2 days and the cookies were absolutely fantastic!  I have a certain someone in my family who rarely has positive things to say, and she ate three cookies and asked for the recipe!  Thank you so very much.

  9. You’re on fire! This recipe keeps coming back to me on Pinterest, need to make it :D

  10. Hi  Lindsay,
    Can’t wait to try this combo as I love 
    both gingerbread and chocolate, but can 
    I shortcut by using a Hershey’s Kiss instead?
    Will it stick or just fall out of the thumbprint?

    • I think you could definitely use a kiss instead, more like a traditional peanut butter blossom! Just add them right when the cookies come out of the oven so they’ll somewhat melt into place.

  11. Oh yum! What a great idea. Last year I made gingerbread cake with chocolate chips; it was marvelous. I bet these are equally as good.

  12. I love this gingerbread theme that is going on here :) These gingerbread thumbprint cookies look so perfect!

  13. They’re gorgeous and I love molasses, gingerbread, and that whole flavor scene like crazy! I have made chocolate chip molasses/gingerbread cookies before and bars and cakes and I would love to try one of your cookies because the combo is just so perfect!

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