I have been wanting to make Whoopie Pies for awhile now.  For some reason the thought of two cake like cookies with filling seems really comforting!  We could all use a little extra comfort right now if you ask me.  These Cookies and Cream Chocolate Whoopie Pies are perfect for just that.  They start with a cake mix which makes them easy to make but the delicious homemade filling is where it is at.  Keep scrolling to see how to make a little comfort for yourself.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

It is not a surprise when I tell you that cookies are comforting.  There are other foods that certainly bring me comfort but cookies are above and beyond my favorite.

When life is uncertain, stressful, happy, sad, needs celebration, boring or even just an ordinary day…I love to bake cookies!

Stress baking however is when make cookie baking skills come to life.  I don’t know what it is but I seem to go outside of my Chocolate Chip Cookie box and broaden by horizons.  Thankfully because these are SO GOOD!

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 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

How to make Cake Mix Whoopie Pies

When your ultimate goal is to have a cake like cookie then starting with a cake mix is a real no-brainer.  Chocolate fudge was my mix of choice.

I wanted the cookies to be extra thick because whoopie pies should be.  In order to get that consistency I started with softened butter, sour cream and eggs.

Mix the ingredients together using a hand held mixer.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

The consistency of the dough will be thick and creamy.  If you end up having small bits of butter in it then don’t worry…so did I.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Another way to get extra thick cookies is to refrigerate the dough.  You could always refrigerate the bowl of dough but I think that scooping it and then refrigerating is better.

Refrigerating the dough scoops for 20-30 minutes on a parchment lined baking sheet will give it just the amount of chill that it needs for the extra height.

Use a small scoop to get a total of 24 {48 cookies total} small cookies or use a medium scoop for 12 {24 cookies total} cookies.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

You can see that the texture has changed a bit after refrigeration.  Roll the ball of dough in your hand and shape the dough ball into a taller mound {another tip for getting thick cookies}.

Bake in a 350 degree oven on a silicone {or parchment} lined baking sheet, for 9-10 minutes for small scoop {11-12 minutes for medium scoop} or until the top and outside is set.  The top should also start to crack.  Unlike some of the other cake mix cookies on my site, you will want to bake these a little longer.

5 Tips for Baking Thick & Cakey Cake Mix Cookies

  1. Add softened butter instead of oil to the dough.  This will give you a thicker dough.  Plus, because butter is a solid fat, it will harden up nicely in the refrigerator.
  2. Refrigerate the dough after it has been scooped for 20-30 minutes.  Refrigerating the dough helps chill the butter which means it will remain solid longer in the oven and that keeps the cookies from spreading.
  3. Shape refrigerated dough into tall mounds.  When you shape the dough into tall cookie dough mounds you are giving the dough farther to bake down.  That will keep it thicker than a cookie you just scoop and bake.
  4. Bake cookies for a little longer than normal cake mix cookies.  Most of the time I have you almost under bake cookies and then they cool completely on the warm baking sheet.  In this case, we want cakey cookies so baking them a little longer gives the cookie the texture you are looking for.
  5. Allow the cookies to cool on a cooling rack, not a baking sheet.  To compensate for baking them longer, we want to be sure that we don’t over bake them.  Removing them from the baking sheet and to a cooling rack straight from the oven will accomplish that.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Homemade Cookies n’ Cream Frosting

Once all of the cookies are baked it is time to make the BEST part…the Cookies and Cream Frosting!  To help keep it from getting too sweet, I used a combination of butter and cream cheese.

Using a hand held mixer, combine the butter and cream cheese until it is soft and creamy.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Add the powdered sugar to the butter and cream cheese.  Mix with hand held mixer until smooth.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

To get the cookie crumbs I used a large Ziploc bag.  You could always use a food processor but I hate to clean something extra.

I used a potato masher to crush the cookies into fine crumbs.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Then I added them to the frosting.  Look at the cookie goodness!

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Mix until the cookies are evenly distributed into the frosting.  Fill a piping bag or large Ziploc bag with frosting and cut a large triangle off of the corner to pipe {the triangle can’t be too small or the cookie pieces won’t go through}.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Now pipe a good amount of frosting onto half of the cookies.  Remember…these are sandwich cookies.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

I think that looks like a pretty tasty tray!

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Finally, top with the other half of the cookies.  Cookies and Cream Chocolate Whoopie Pies are now complete!

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

When these chocolate whoopie pies were finished, I promptly ate 3 and then decided they were too dangerous to have at home.  So I wrapped them up and gave them to a friend for her birthday.

I think that anyone would be happy to get these sweet babies for any occasion… like a random Sunday afternoon.

 Cookies and Cream Chocolate Whoopie Pies featured by top US cookie blog, Practically Homemade

Do you love desserts with cookies in them?  Try these recipes…

Cookies and Cream Chocolate Whoopie Pies

Chocolate cake mix is transformed into thick and cakey Whoopie Pie cookies that are filled with homemade Cookies and Cream frosting. The perfect cookie!

Course Dessert
Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Servings 24 sandwich cookies

Ingredients

Cookie

  • 1 box chocolate cake mix
  • 1/2 cup butter {softened}
  • 3 eggs
  • 1/4 cup sour cream

Cookies n' Cream Frosting

  • 1/2 cup butter {softened}
  • 4 oz. cream cheese {softened}
  • 2 cups powdered sugar
  • 1/2 cup chocolate sandwich cookies {crushed}-about 8 cookies

Instructions

Cookies

  1. Preheat oven to 350° and cover baking sheets with silicone liners or parchment paper.

  2. In a medium bowl combine cake mix, butter, eggs and sour cream. Using a hand held mixer {or mix by hand}, mix the ingredients until just combined. There may be small bits of butter in the dough.

  3. Scoop dough onto a parchment lined baking sheet using a small cookie scoop {you should get 48 small cookie mounds}. Refrigerate the dough scoops for 20-30 minutes.

  4. Once chilled, add a dozen cookie scoops to a cookie sheet and bake for 9-10 minutes or until the edges and top of the cookie are set and the top is starting to crack. Move cookies immediately to a cooling rack to cool completely. Continue until all of the cookies are baked.

Frosting

  1. In a medium bowl combine butter and cream cheese. Use a hand held mixer to mix until creamy and smooth. Add powdered sugar and mix until completely incorporated.

  2. In a large Ziploc bag {or food processor}, crush chocolate sandwich cookies. Add crushed cookies to the frosting and mix until the cookies are evenly incorporated. Put frosting into a piping bag {or large Ziploc bag} and cut a large triangle {a small triangle won't allow the cookies to go through}.

Finishing the Whoopie Pies

  1. Pipe a generous amount of Cookies and Cream frosting onto half of the cookies and top with the other half of the cookies. Serve or store in an airtight container at room temperature for up to 4 days. These chocolate whoopie pies are also great refrigerated for up to 5 days and frozen for up to 3 months.