Crowning Jewel Cherry Pie Cobbler

It’s been a very rough week for me recently! I sprained my knee for the second time in less than a year….again while holding my son. I’m at the end of recovering from stomach flu among other things & to top it all off it’s another cold & rainy day in the South East….guys I’ve just about had it with life & winter this year and am seriously considering migrating to the tropics and returning with the birds in April…Lol!

So I said a silent prayer before losing my sanity and did what I always do when in need of comfort…..cooked, well actually this time I baked!

It’s the perfect day for a comfort food dessert & I’ve got another quick and easy one for you cobbler lovers out there! I call it Crown Jewel Cherry Pie Cobbler because it’s guest star is the crowning glory of the tropics…Pineapple & it marries nicely with good ole cherry pie, made simple in cobbler form! I really loved making it extra special with the vanilla sugar added to the filling and don’t you dare forget to serve it hot out of the oven with a scoop of heavenly softened vanilla ice cream melting all over it and sprinkled with cinnamon…i will find out and ban you from the national pie eaters association which I am a honorary member of…Lol! Because a cobbler just isn’t a cobbler & a pie is not a pie without a la mode…a scoop of ice cream!

Cooks Notes:

Feel free to make it without the pineapples. It will still be cherry pie cobbler and absolutely delicious.

My go-to canned pie filling is Duncan Hines Comstock brand & the Simply Collection which are not loaded with extra sweeteners & additives.

My favorite brand of yellow cake mix is Betty Crocker Supermoist cake mix, it has a nice buttery sweetness and stays moist yet firm for the perfect cobbler texture.

I also will occasionally change it up and just use 2 deep dish pie crusts and just break it into chunks to top my fruit filling and its just as delicious just with a more crisp texture.

Be sure to pat the cake mix very well into the juices of the fruit filling to cook it through and keep it moist.

Melting the butter does not work as well as slices of cold butter evenly distributed atop the cake mix so that it cooks yet stays moist. You can also cut your butter into slices and then freeze for 5 minutes before using it to keep it cold.

Refrigerate and warm in microwave for leftovers

* Serves 6


  • 1 box of super-moist yellow cake mix
  • 1 large can of cherry pie filling
  • 1 large can of pineapple chunks, reserve 1/2 the juice (optional)
  • 1 or 2 sticks of butter, sliced
  • 1 tablespoon of pure vanilla extract
  • 1 teaspoon of quality ground cinnamon plus extra for garnish
  • French Vanilla Ice Cream
  • 1/8 cup vanilla sugar which is half of your vanilla sugar mixture

(recipe is 1/4 cup granulated sugar + 1 tablespoon softened butter + 1 tablespoon pure vanilla extract. Mix well and use half of the mixture in this recipe then store the rest in a jar.


  • Preheat oven to 350 degrees Fahrenheit and spray a medium baking dish with cooking spray.
  • Fill your baking dish with cherry pie filling and canned pineapple and distribute evenly across the surface of the baking dish then add 1/2 of your vanilla sugar mixture and one teaspoon of cinnamon and mix very well.
  • Top evenly with yellow cake mix and use a wooden spoon or utensil to firmly press cake mix into the filling. This is very important to ensure the cake mix cooks and stays moist.
  • Place slices of butter evenly across the entire surface of the cake mix, working fast so that the butter stays cold. Cover as much surface area as possible with slices of butter.
  • Bake for 40 minutes or until golden brown and crisp.
  • Serve hot or room temperature with vanilla ice cream and and sprinkled with cinnamon.

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