Chocolate Cherry Thumbprint Cookies

Chocolate Cherry Thumbprints|Frankly Entertaining

Thanks to Imperial Sugar for helping with today’s recipe.

Today I’m posting my first recipe for #Choctoberfest. I definitely think #Choctoberfest is a celebration that I can get behind. What’s not to love about dozens of bloggers getting together to celebrate their love of chocolate! I have a couple of recipes to share. Today’s is a recipe that I really thought about because I want it to be delicious (obviously) and I wanted it to look good. So, if I’m being completely honest with you, this recipe probably doesn’t need the white chocolate drizzle, but I thought it added a nice contrast! My kids ate all the drizzle ones and I ate more than my fair share of the plain ones!

Chocolate Cherry Thumbprints|Frankly Entertaining

One of my favorite flavor combinations is chocolate and cherry, and so this cookie seemed like a natural extension of everything that I hold near and dear.

I used a store brand cherry jam and it’s just the right balance with the chocolate. My husband’s comment was, “they’re sweet,” and I think that’s perfect when Imperial Sugar sent me 40lbs of sugar (my UPS guy must love me!)! I used a baby spoon to get the perfect amount of jam onto the cookies before baking. If you have little helpers, creating the thumbprints is a perfect job for little hands and thumbs! I also used a mini cookie scoop, and this recipe made 5 dozen of the mini cookies.

Chocolate Cherry Thumbprints|Frankly Entertaining

Don’t forget to enter the giveaway, and be sure to check out today’s other #Choctober recipes at the end of the post.

Chocolate Cherry Thumbprints


  • 1 c. butter
  • 1 1/4 c. Imperial Sugar + 1/4 c. for rolling
  • 2 eggs
  • 1/2 c. cocoa
  • 2 1/4 c. flour
  • pinch of salt
  • 1 tsp. baking powder
  • 1/2 c. cherry jam


  1. Cream together butter and sugar until smooth.
  2. Add eggs and mix.
  3. In a separate bowl combine dry ingredients (except for the extra sugar for rolling), and add to the butter mixture.
  4. Use a mini scoop to create balls of dough.
  5. Roll dough balls in sugar and create an indentation with your thumb.
  6. Add 1/2 tsp of jam to each indentation.
  7. Bake at 375º for ten minutes. Cool on a wire rack.


Thank you to the sponsors who make #Choctoberfest possible! This year, Imperial Sugar is back as our Gold Sponsor. They have been a trusted name in kitchens since 1843, and their website is home to thousands of sweet recipes tested in the Imperial Sugar Kitchen. You can find Imperial Sugar on Pinterest, Facebook, Instagram, Twitter, and Youtube, or join their Sweet Community so you can share your own recipes, save recipes to a virtual inbox, print Imperial Sugar coupons, and connect with other sugar lovers.

Imperial Sugar and our silver sponsors have banded together to offer a huge #Choctoberfest prize pack, which you can enter to win below! One lucky winner will be chosen at random to receive the following:

  • From our Gold Sponsor Imperial Sugar: 1 case of granulated sugar (40 pounds), 1 case of brown sugar (24 pounds), 1 case of dark brown sugar (24 pounds), 1 case of powdered sugar (24 pounds bags), and an Imperial Sugar red ruffle apron
  • From our Silver Sponsor Nature Nate’s: 32 oz. Raw & Unfiltered Honey bottle, Honey Syrup, Honey Packets, a Nature Nate’s T-shirt, various kitchen supplies, and $50 Amazon gift card
  • From our Silver Sponsor Barlean’s:16 oz Barlean’s Butter-Flavored Coconut Oil, 9.52 oz canister of Chocolate Silk Greens, and 8oz bottle of Essential Women Omega-Swirl Chocolate Mint
  • From our Silver Sponsor Caveman Coffee: 1 Bag of Coffee (you choice of blacklisted or sabertooth), 1 coconut MCT oil, and 1 Cacao Butter
  • From #Choctoberfest blog hosts The PinterTest Kitchen: 1 specialty chocolate gift pack (your choice of dark or milk chocolate), 1 tin (14 ounces) drinking chocolate, and Divine’s Fair Trade Gift Set

Chocolate Cherry Thumbprints|Frankly Entertaining

Enter now to win our #Choctoberfest 2016 prize pack! We’ll be picking a winner at random winner on Saturday, Oct. 22, so enter by Friday to make sure your name is in the drawing:

a Rafflecopter giveaway

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