Reconstructed “Oreo” sandwich cookies

2 Apr

For April Fool’s Day yesterday we had our good friends over for dinner, and I knew I wanted to make something “disguised” for dessert. I had been contemplating making ice cream cupcakes for a while, so armed with a recipe for Brownie Bottom Ice Cream Cupcakes from Joy the Baker, I tried to see what I could do to make some fun filling with cake and ice cream.

While I normally don’t make box cake, the reality is that when you freeze ice cream cake, the texture and flavor of scratch cake gets lost. Unless you specifically need to avoid certain ingredients, save yourself the trouble and just use a box cake mix.

I was going to go with Oreo double stuffed cookies, but while I was at the grocery store, I spotted Who Nu? cookies, which are packed with extra nutrition. If I’m going to serve these to kids, I might as well try to make myself feel less guilty, right?


36 chocolate sandwich cookies
1 box white cake mix
1 gallon vanilla ice cream or any flavor that is white (not French vanilla)
Hot water


36 foil cupcake liners
9″ icing spatula
wax paper
aluminum foil


36 ice cream cake sandwich cookies


  1. Drop the foil cupcake liners into cupcake pans.
  2. Unscrew the chocolate sandwich cookies, trying as hard as you can to keep all of the cream filling to one side. Drop the uncreamy sides, decorated face down, into the liners, one into each. Save the other cookie halves.
  3. Prepare the cake mix according to directions.
  4. Drop one generous tablespoon of batter on top of each cookie, taking care not to fill each well any more than 1/4 full.
  5. Pick the pans up and drop onto the counter from an inch or two to eliminate as much air as you can. Do this a couple times.
  6. Bake according to cake directions, but pull them out a few minutes early, as you’re only making half a cupcake. Test with a toothpick or cake tester to make sure it’s done.
  7. Let the cupcakes rest in the trays for 10 minutes.
  8. Place the trays with the cupcakes in the freezer for 30 minutes. Meanwhile, let the ice cream thaw so that it is malleable but not liquid.
  9. Fill the cupcakes to the top of the liners with the ice cream, using the spatula to pack it in and smooth the top. Dip the spatula in hot water to help cut through the ice cream. Try to work out as much air as you can, but take care not to squish the cupcake.
  10. Place the reserved cookie halves in the center of the cupcakes, decorated face up.
  11. Place the cupcakes back in their trays. Cover with wax paper, and then wrap the whole thing in aluminum foil.
  12. Freeze for at least two hours, preferably four.
  13. Remove the cupcakes from their trays. Using a sharp thin knife, cut straight down, tracing the outline of the cookie to trim the excess ice cream and cake away.
  14. Remove the foil wrappers and excess material. Use a spatula to smooth the edges.


Like any ice cream cake, this takes a long time and a lot of patience. Also, make sure the ice cream is pretty solid before you serve, as the concoction will be easily crushed. I’m second-guessing using a premium ice cream, as the higher fat content keeps it softer. I might (gulp) even think about using light ice cream to keep the fat content down.


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