Chocolate Chip Covered Oreo Cookies

These are the most decadent cookies I’ve made yet.


First, make a batch of chocolate chip cookie dough.  Use your favorite.  Here’s the one I used (oz are by weight):

Cream in mixer for two minutes:

2 sticks butter, softened

8 oz brown sugar

2 oz white sugar


2 eggs

1½ teaspoon vanilla extract

Separately, mix:

12oz all-purpose flour

1/2 teaspoon sea salt

1 teaspoon baking soda

and slowly add to wet mixture.  Incorporate:

8 oz chocolate chips (dark belgian chocolate chips are good)

OK, then, spray a bowl with cooking spray and set outside to cool:

If you don’t have a snowy woodpile, a refrigerator or freezer would suffice.

Next, spread out 18 Double-stuff Oreos on an insulated jelly roll pan, and set on top of the woodstove:

The temperature here was 113° F:

If you don’t have a woodstove, a warming oven, or a second oven about 120° F would do.  The idea is to make the cookies warm enough that they’re not cooling the cookie from the inside while they’re baking, but if this goes on too long or too hot, there will be a gooey cookie mess.  Once the top cookie rotates freely, it’s warm enough.  This took about 15 minutes.

Pre-heat the oven to 325° F (but see discussion of temperatures below).

Spray some cupcake tins with cooking spray:

Set out a rolling mat, or flour a counter with the chilled dough (use more flour than shown in this picture):

and flour the dough as you roll it out (this is sticky dough):

The final thickness of the dough will be determined by the thickness of the chocolate chips:

What you’re going for is about 1/4″ thick:

Now, take a biscuit cutter and cut the dough into as many disks as will fit:

Gently remove the excess and lift the disks into the cupcake tin:

Now, place an Oreo in each tin.  Try to center them as well as possible:

And then add a disk to the top of each one:

It’s not necessary to seal the top to the bottom, but I did push the edges down a bit, to make a bit of a dough dome.

These are set for the oven.  Place on the middle rack and bake for 17 minutes.  I’ve verified that my (gas) oven’s thermostat is property calibrated, but many recipes assume an oven that runs too hot, so if your oven runs hot, reduce the cooking time.  Here’s what they look like when they’re done:

Set them outside on the woodpile to cool for 10 minutes (photo is of second batch):

While the first batch is baking, roll out the rest of the dough:

and when you’re down to the last of the dough, it helps to just mark the dough before cutting, so you can count out an even number of tops and bottoms:

In the end, I had 36 rounds, for 18 tops and 18 bottoms.

Now, then, bring the cooled cookies inside and gently run a butter knife around the edge to make sure they don’t stick.  Transfer to a cooling rack to finish cooling through to room temperature (as if you’re not going to eat one hot…):


]( I made these as a gift, so I arranged them on a plate:

Now then, about temperature.  Here are two cookies, the left is baked at 350° F and the right is baked at 325° F:

At 350, the cookie does not rise as high and is more cooked through.  At 325, you get a higher rise, and a more gooey chocolate chip batter.  I find the 325 cookies to be the most popular, but it’s a matter of personal taste.  At 350, bake for 14 minutes instead of 17.

Here are some inside shots, again 350 on the left, and 325 on the right:

Enjoy!  A full glass of milk is required per cookie.  I guess that’s not really a surprise, since these are really four cookies in one.  Best to have these only once a year!