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These pillowy soft chocolate sandwich cookies are filled with whipped cream (dairy free or not), flavored with coffee and vanilla and chilled for a happy straight from the fridge dessert.

This recipe is based on my Gram’s chocolate drop cookies. Whenever we went over to my grandparents house, my Gram would often have a plate of her famous cookies chilling in the fridge. Opening up the fridge and finding my favorite cookies or a bowl of my Gram’s cucumber salad was my most enduring memory of my Gram’s love.

The texture of these cookies is closer to cake then a cookie. They’re similar to whoopie pies, yet Gram ALWAYS filled them with Cool Whip. I’ve tweaked the recipe to make them dairy free, though I’ll let you know the swaps so that you can make them with full fat dairy if you’d like.

Whatever you choose, these soft chocolate sandwich cookies are guaranteed to bring smiles.

soft chocolate sandwich cookies on plate

Soft chocolate sandwich cookies recipe

sifting cocoa, scooping cookies, finished filled chocolate sandwich cookie

Chocolate sandwich cookie origins

We don’t really know where my Gram got this recipe. It was in her recipe book on a simple handwritten, well-used recipe card. As I said, it is similar to whoopie pies. The difference

Did Gram see a whoopie pie recipe and make her own version that made more sense to her? We don’t know! It’s always fun to find these treasured family recipes and try to figure out where it came from.

Recipe redux: nix the #1 most important vintage ingredient

In the original recipe, My Gram made her cookies with Crisco. Vegetable shortening definitely is what gives these cookies their shape–they should dome in the middle like a cake. Butter does NOT work as it produces a flatter, crispy cookie.

Periodically over the years, I’ve tried different iterations of my Gram’s recipe because I don’t use vegetable shortening in my kitchen. I know shortening was common in the 50s. It’s cheaper, yes, but that cheapness comes with the downside of being highly highly processed. Over the past couple years, I’ve steered completely away from seed oils in my home cooking, opting for animal fats and less processed cold pressed, virgin or unrefined non-seed oils (like avocado, coconut, and olive oil).

You can do your own research on seed oils, but the question for this recipe remains. If Gram’s Crisco is out for this recipe, what can you use instead that’ll give you the same texture?

After many experiments over years, the one I’m happiest with is coconut oil.

Coconut oil, being a solid at room temp oil has a similar texture to vegetable shortening. Lard also works, but the cookies have a decided lard flavor if you use it. If this were a savory recipe, I’d go for the lard.

chocolate sandwich cookies filled with whipped cream

Soft Chocolate sandwich cookies ingredients

Coconut oil (vegetable shortening in the original recipe).
Sugar (I cut my Gram’s original amount by 1/3).
Egg.
vanilla: for flavor.
Flour: all-purpose.
Cocoa: Dutch process like Droste, Hershey’s, or Hershey’s Special Dark
Baking powder: makes them poofy.
Salt: for flavor
Brewed coffee (Use milk if you’re okay with dairy)
Whipping cream: use coconut cream for non-dairy or full-fat whipping cream for a dairy version; both are sweetened lightly with powdered sugar and flavored with vanilla.

Tricks to the best soft chocolate sandwich cookies

scooping out chocolate drop cookie batter

Use a spoon: Scrape a spoon against the side of your bowl to get the perfect rounded oval of batter, then squidge it off the end with your finger. Don’t use a scoop–they’d be too perfect, and in this case that’s boring.
Sift the cocoa and flour: Good cocoa powder is lumpy because of the presence of fat in the cocoa. It must be sifted to avoid lumps in the batter. The easiest way to do this is either with a sifter device or with a strainer. Sifting everything twice will also make sure that the baking powder and salt are evenly distributed in the dry ingredients before you mix them into the wet ingredients.
Parchment tricks: Being cakey, these cookies have delicate bottoms that can fall apart easily if you’re not being careful. Allow the cookies to cool completely on a piece of parchment. Then peel off the parchment carefully to release the cookies.
Fill now or later: If you want a softer cookie, whip your cream and fill the cookies, then chill them for a couple hours. You can also fill them on demand just before serving. The texture will be different, but no one will be sad.

Chocolate Drop Cookie Sandwiches

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Author: Elizabeth Farr
Total Time: 27 minutes
Yield: 12 sandwiches

Print Recipe

Description

These are the cookies of my childhood. When I opened the door of my Gram’s fridge to find a plate of these whipped cream filled rich cakey chocolate joys, I felt loved. (Dairy free)

Ingredients

Scale

8 Tablespoons coconut oil (120 g)
2/3 cup sugar (133 g)
2 eggs, at room temperature
1 teaspoon vanilla extract or paste
1 and 1/2 cups all-purpose flour (195 g)
6 Tablespoons dark cocoa powder such as Hershey’s Special Dark (30 g)
3/4 teaspoon baking powder
1/2 teaspoon salt
1/2 cup brewed coffee, cold (118 mL)

Filling

1 cup canned coconut cream or coconut whipping cream
2 Tablespoons powdered sugar
1/2 tsp vanilla extract or paste

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Instructions

Preheat the oven to 350 F (180 C).
Line two baking sheets with parchment. Set the racks on the oven in the upper and bottom thirds. This will let you bake 2 sheets at the same time.
Beat the coconut oil and sugar in the bowl of a stand mixer until it is fluffy.
Add in the egg and vanilla and beat until you have a smooth mixture.
Whisk the flour, cocoa, baking powder and salt in a small bowl.
Add about 1/3 of the flour mixture to the coconut oil mixture, then mix until the flour just disappears.
To finish the batter, add in half of the coffee, another 1/3 of the flour, the rest of the coffee, then the rest of the flour. Mix each addition briefly before adding the next.
Finish off by scraping the bowl all the way to the bottom and folding the batter over on itself a few times so the batter is well mixed.
Scrape the batter into a large soup spoon, then slide it off your finger onto one of the prepared sheets. Finish scooping all the cookies onto the baking sheets.
Bake for 6 minutes.
Open the oven and spin the baking trays 180 degrees, then swap them from top to bottom and bottom to top.
Bake for another 6 minutes. They’re done when the middle springs back on one of cookies when you lightly press it.
Let the cookies cool completely on a wire rack.
When you’re ready to serve them, whip the whipping cream with the powdered sugar and the vanilla for the filling with a stand mixer or a hand mixer until it holds stiff peaks.
Flip over one of the cookies and spoon a scoop of the whipped cream on top.
Cover the whipped cream with a second cookie to make a sandwich.
Fill the rest of the cookies.
Serve the cookies on a large platter immediately.
Save any extra cookies in the fridge, covered for up to 2 days.

Notes

Make it with dairy: If dairy doesn’t bother you, feel free to use heavy whipping cream in place of the coconut cream, and swap in milk for the coffee. Do NOT however make these with butter. The original recipe calls for shortening, and I can attest that using butter in place of shortening here makes for a cookie that is too crisp and flat.

Prep Time: 5 minutes
Additional Time: 10 minutes
Cook Time: 12 minutes
Category: Family favorites
Cuisine: American