Soft Homemade Oreos with Vanilla Buttercream

Milk’s favorite cookie is getting a major makeover with these soft homemade Oreos. Imagine soft (but not cakey) chocolate sugar cookies, filled with a thick layer of fluffy vanilla buttercream. These homemade Oreo cookies are rich, buttery, and creamy, with a delicious balance of dark chocolate and vanilla.

Who doesn’t love an Oreo cookie? Dunked in milk, crumbled into ice cream, or baked into a cookies and cream cake, they’re delicious and so fun to eat. These soft-baked homemade Oreos, though, put the crunchy packaged cookies to shame. I bet you can’t eat just one!

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Ingredients

Soft Chocolate Sugar Cookies

While traditional Oreos are hard and crunchy, my chocolate sugar cookie dough bakes up soft and buttery. It also holds its shape perfectly, so you can use any shape of cookie cutter that you like. Note that these are not cakey, like you would get with Oreo Cakesters or whoopie pies.

• All-Purpose Flour. Provides strength and structure to the sugar cookies.
• Unsweetened Cocoa Powder. Adds rich, dark chocolate flavor. I suggest using a good-quality Dutch-processed cocoa powder.
• Powdered Sugar. Sweetens the sugar cookies, while the fine texture of the powdered sugar makes them soft and tender.
• Salt. Coarse Kosher salt balances the sweetness and enhances the flavor of the chocolate.
• Unsalted Butter. Adds moisture, flavor and fat. When the cookies bake, the water evaporates from the butter and creates steam. The steam fills the cookie with little pockets of air which creates tiny flaky layers for tender, buttery chocolate sugar cookies.
• Vanilla Extract. Good-quality vanilla extract adds flavor, and enhances the richness of the cocoa powder.
• Milk. A splash of whole milk adds moisture to the chocolate sugar cookie dough and binds it together, without the use of an egg, which would make the cookies puff and spread.

Filling

For the filling, I turned to my trusty American Buttercream Recipe. It’s so light, silky, fluffy, and not at all too sweet. And if you want to fill your soft homemade Oreos with something other than vanilla buttercream, then any flavor will do. Pink raspberry buttercream would be delicious with the chocolate sugar cookies, and perfect for Valentine’s Day. Peanut butter would be incredible.

• Unsalted Butter. Butter makes buttercream rich, creamy, flavorful and fluffy when it’s whipped with powdered sugar.
• Powdered Sugar. Sweetens and thickens the buttercream.
• Meringue Powder. Adds stability and improves the texture.
• Vanilla Extract. Use a good-quality vanilla extract for the best flavor.
• Milk. I usually add a small splash of milk to my buttercream if it’s too thick for spreading onto a cake. But for filling these homemade Oreos, you may not need it since the filling should be a bit thicker than what you’d use for cake decorating.

Instructions

Make the cookies.

• Prepare a 1/2 batch of the Chocolate Sugar Cookie Dough as instructed. Wrap the dough in plastic wrap, and chill for 20 minutes before rolling out.
• Line several large baking sheets with parchment paper.
• Dust a clean work surface with cocoa powder, and roll the dough out to an even thickness of about 1/8 inch thick, using more cocoa powder as needed to keep it from sticking.
• Use a 1 1/2 inch round cutter to cut as many cookies as you can, placing them 1 inch apart on the baking sheets. Gather up the scraps of dough, re-roll the dough and continue cutting cookies. I was able to cut 54 cookies, for a total of 27 assembled Oreos.
• Place the baking sheets in the refrigerator and chill for 45 minutes; the chilling helps prevent the cookies from spreading.
• Preheat the oven to 350F. Bake the chilled cookies on the center oven rack for about 8 – 8 1/2 minutes, until you no longer see any wet patches of dough. Cool on the pan for 5 minutes, then gently transfer to a cooling rack to cool completely.

Make the buttercream.

• Prepare the Perfect American Buttercream as instructed. You can make it any flavor that you like, and my post has many suggestions for flavor variations. If you want your buttercream a little stiffer for filling your cookies, you can eliminate the milk, but I made it as written for my Oreos.
• Fit a piping bag with a small open star tip, such as #32, and fill with buttercream.
• Turn over half of the cooled cookies. Pipe a swirl of buttercream onto the bottoms of half the cookies, then top each with another cookie to make a sandwich.

Frequently Asked Questions

What kind of cocoa powder should I use for the chocolate cookies?

• Dutch-Processed Cocoa Powder vs. Natural Cocoa Powder. Understanding the difference between types of cocoa powders is key to choosing one for your cookies, cakes and other baked goods. Dutch-processed cocoa powder is more mellow tasting, less bitter, and darker in color. Natural cocoa powder is stronger and more bitter. I get into this subject in a bit more depth in my favorite chocolate cake recipe, so be sure to give that a read.
• Personally, I don’t even keep natural cocoa powder on hand, and I only use Dutch-processed cocoa for all of my baking. I used Hershey’s Special Dark for years, but not so much in the last year or so since they changed the formula. Mostly I will use Rodelle or Drost Dutch-processed cocoa powders for my baking.

Do homemade Oreos taste like Oreo Cakesters?

• No, this recipe is not similar to a cakester or whoopie pie type of sandwich cookie. These are soft-baked sugar cookies with a buttery, crumbly texture.

Can I make and freeze the cookie dough ahead of time?

• Yes, sugar cookie dough freezes very well. Make the dough as instructed, shape into a disk, and wrap in plastic wrap. Label the plastic, then refrigerate for up to 5 days, or freeze for 3-6 months. Let frozen dough thaw overnight in the refrigerator, then allow the dough to warm up to room temperature for about an hour. It should still be cool to the touch, but pliable enough to roll out without too much difficulty.

How thin should I roll the cookie dough?

• Normally, I roll my sugar cookies 1/4 inch thick. For sandwich cookies, though, you should roll the dough out to 1/8 inch thick.

What size cookie cutter should I use to cut the Oreos?

• I used a 1 1/2 inch round cookie cutter, but you could go as big as 2 inches.

How many assembled chocolate sandwich cookies does this recipe make?

• Using a 1 1/2 inch cutter, I was able to cut 54 chocolate sugar cookies, for a total of 27 filled homemade Oreos.

What piping tip did you use to fill the cookies?

• I used tip #32 for piping the buttercream filling.

How should I store homemade Oreos?

• You should store leftover homemade Oreos in an airtight container. Refrigerate the cookies for up to 2 weeks, or freeze for 3-6 months.

What other flavors of buttercream could I use to fill the cookies?

• In my post for Perfect American Buttercream, you’ll find many flavor variations that you can try. Besides vanilla, I’d suggest peanut butter, strawberry, raspberry, caramel, chocolate, espresso or mint buttercream.

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