Homemade Crunchy Chocolate Sandwich Cookies

*Originally posted in March 2020 at the height of the lockdown*

I ended up laying on our bed watching How It's Made on my phone with my children and Sandwich Cookies was one of the videos. With lots of time on our hands, we decided to make our own sandwich cookies.

Unlike Whoopie Pies, which are like small soft cake sandwiches, I wanted to make a crispy cookie, like Oreos. Oreos are one of my favourite cookies. Not the filling, mind you, but the crispy, deeply chocolatey biscuit. I could eat a whole box... which is why we hardly ever by them!

I haven't been able to replicate the Oreo cookie's perfect chocolate biscuit but this recipe makes delicious cookies well worth trying.

The recipe below will make about 28 sandwich cookies plus a bunch of extra chocolate dough which you can freeze and use later, or bake and eat without the filling!

I started with a recipe for "Rolo cookies" where you wrap the dough around a Rolo and bake. (Those cookies are divine!) To make the dough more crispy, I used an egg plus an egg yolk instead of two eggs; cut the leavener (baking soda) in half and upped the cocoa which was originally 3/4C.

COOKIE DOUGH

16 tbls (half pound) of butter at room temperature

1 Cup firmly packed brown sugar

1 Cup white sugar

2 tsp vanilla

1 egg plus 1 egg yolk

360g of flour (2 1/4 cups with the 'scoop and level' way of measuring)

100g cocoa (about 1 cup)

1/2 tsp baking soda

1/2 tsp salt

In a mixer or by hand, beat together the butter and sugar, then add the egg and egg yolk, and vanilla. Beat until light and fluffy.

In a separate bowl, add flour, salt and baking soda then sift in cocoa and whisk together.

Add the dry to the wet and mix until combined but don't over mix.

Split dough into two, shape into disks, wrap in plastic and chill for a half hour.

FILLING

210 g of icing sugar

80 g of butter (about 5 tblsp)

30 g of vegetable shortening

1 tsp vanilla

Beat together until very fluffy.

Baking and Assembly

Pre-heat oven to 350F

Flour your working surface and rolling pin and roll out dough to about 3mm. If using an embossing roller as I did, roll it out a bit thicker with your regular roller then use the embossing roller for one last pass.

Cut out cookies with a 2 inch round cutter.

Transfer cookies to a baking sheet lined with parchment.

Bake for about 10 minutes. Dark cookies are a bit tricky because you can't tell as easily when they are done. Smell, and look at the edges very carefully. If your oven is hotter than mine or convection, the timing may differ.

Take off the pan and cool on a rack.

Once the cookies are completely cooled, beat the filling again until it is light and fluffy. I found the easiest way was to pipe the filling on the cookie so I didn't have to press with a knife or spatula and risk breaking the cookie. I used an old milk bag, that I had washed and saved, as my piping bag. I cut one of the corners off and it worked perfectly.

And there you have it! Delicious crispy chocolate sandwich cookies!