Chocolate Thumbprint Cookies with Red Wine Raspberry Jam

Red wine and raspberry jam (via Chocolate thumbprint cookies with red wine raspberry jam (via yes, we are mixing two of my favorite treats to make these cookies: red wine and chocolate. Mmmm. These cookies are slightly chewy with a little pool of sweet and spicy jam at the center of each. They are not only delicious but really fun to make as adding the thumbprints feels a lot like playing with Play-Doh (but tastes nothing like eating Play-Doh).


Chocolate thumbprint cookies with red wine raspberry jam (via The inspiration for these come from Mindy Segal and Kate Leahy’s book, Cookie Love. They share a recipe for a Lambic strawberry jam (paired with a PB thumbprint cookie) that I haven’t gotten to make yet, but it’s HIGH on my list. Sounds amazing, right? And it got me thinking about other fun, boozy liquids that could be added to easy homemade jams. Once I decided I’d try something with red wine, pairing it with a chocolate cookie seemed only natural to me. Anyway, I’ve only made a couple recipes from this book so far, but I’m excited to try more as I’m already a big fan, seeing it’s already inspiring me to explore other combos already. So, thought I’d share in case you need a good cookie cookbook in your life. 🙂

Chocolate thumbprint cookies with red wine raspberry jam (via Chocolate Thumbprint Cookies with Red Wine Raspberry Jam, makes 12 cookies and about 2/3 cup jam

For the cookies:
1/2 cup softened butter
1/3 cup sugar
1 egg
1 teaspoon vanilla extract
3/4 cup all-purpose flour
1/4 cup cocoa
sanding sugar for the edges (optional)

For the jam:
1/2 cup red wine (something bold that you like drinking)
1/2 cup sugar
1/2 teaspoon vanilla extract
6 oz. raspberries

First get the jam going by combining the wine, sugar, vanilla extract, and raspberries in a small pot. If you are using frozen raspberries, thaw them first. Cook over low heat, stirring until the sugar dissolves. The raspberries will likely begin to breakdown here, but you can also use the edge of a wooden mixing spoon to smash them up some. Then increase the heat to medium so that the liquid begins to boil. Keep the boil low and steady; you don’t want it to boil over the edges of the pot. Allow to cook for 15-20 minutes, stirring every now and again, until the mixture is thick enough that it easily coats the spoon. As the jam cools, it will thicken a bit more.

Red wine and raspberry jam (via the jam is cooking, you can start on the cookies. In a large mixing bowl, cream together the butter and sugar until well blended. Add the vanilla extract and egg and stir until just combined. In a separate, smaller bowl, whisk or sift together the flour and cocoa. Add the dry mixture to the butter mixture in two batches, stirring in between, until a thick dough forms. Cover and refrigerate for 2 hours or in the freezer for 15 minutes.

Divide into twelve small balls. Flatten the bottom of one side and on the other side press a deep hole with your thumb. You don’t want to press a hole all the way through the dough, but don’t be afraid to make it quite deep as these will even out/puff a little when baked and you want plenty of space for your jam to sit in. Maybe these should be called jam thrones from now on? Hmmm. If you are using the sanding sugar, roll the edges of each cookie in that now.

Bake on a baking sheet covered with a baking mat or parchment paper at 350°F for 8-9 minutes. Remove to a cooling rack and allow to cool for a couple minutes before adding the jam.

Chocolate thumbprint cookies with red wine raspberry jam (via These are so fun! A little red wine, a little chocolate, plenty of wine left in the bottle to enjoy a glass still too – perfection. Happy baking! xo. Emma

Credits // Author and Photography: Emma Chapman. Photos edited with A Beautiful Mess actions

  • Can gluten free one-for-one flour be substituted? Will sifting said flower a couple of times help lighten it and keep the cookies from becoming stodgy? Is there a substitute for butter that you would recommend to someone who cannot eat dairy or is vegan?

  • Try putting the cookies in the fridge for 15 minutes before you actually cook them. This should help them firm up and not lose their shape.

  • Actually I´m in Germany, maybe some of the ingredients have a different consistency?

  • yeah, I had the same problem, wondered if something went wrong in translating a US recipe to the UK, but maybe not if you’re in the US and had the same problem?

  • These are incredible but they lost their shape in the oven. Is there anyway to prevent that?

  • Made these the night you posted them – holy cow – so stinking good! They are now gone. Haha. But I had some leftover jam that made it onto a PB&J today. Delicious. Thanks Emma!

  • How can one transport a bunch of these without using multiple containers and without messing up the filling? Is there a product you recommend? Thanks!

    • My grandmother made jam thumbprints every year for the holidays. They are essentially the same as these. The jam thumbprints, as I recall, were packed with a sheet of waxed paper between layers. Even though we lived in another state for many of the years Grandma was baking, she always shipped us about a years supply (Mom would put a tray out everytime we had company over, which was often) of about 20 different cookies. She packed them in coffee cans, cookie tins, and shoe boxes, then packed those into a shipping box. Everything arrived intact and undamaged.

  • I would use a fruit juice (grape would work well). A little balsamic vinegar might be a really fun addition but I am not sure if 1/2 cup might be too much and overwhelm the flavor of the jam. My guess (without testing) would be that it would. So I would use a fruit juice as a substitute, which would mean you could use a little less sugar as well. 🙂


  • If I had to make this without wine to share with toddlers, what can I substitute it with? balsamic vinegar maybe?

  • I ate some of the remaining jam from this batch on a bagel one morning and it was SOOOO good. Probably a bit too much sugar for breakfast but I can’t resist leftovers sometimes. 🙂


  • You only have to use some of the bottle… what you do with the rest of the opened bottle of wine is totally up to you. 🙂


  • I do have to try that red wine raspberry, it sounds so delicious! And of course the cookies sound wonderful as well!

  • Are you really saying this wine would survive till the end of baking? 😉

  • These look so good!!! I might have to try making them.

  • These look delicious Emma!! Even though it’s only breakfast time here in Australia, I’m tempted to make some right now 🙂

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