Upside Down Cookies Recipe -
Upside Down Cookies Recipe

Upside Down Cookies

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"A festive layered cookie with cinnamon. Easy and delicious cookies!!"

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Ingredients Edit and Save

Original recipe makes 12 cookies Change Servings


  1. Preheat oven to 400 degrees F (200 degrees C). Grease a muffin pan.
  2. In a medium bowl, stir together flour, sugar, baking powder, and cream of tartar. Cut in shortening until mixture resembles coarse crumbs. Sprinkle on the milk, and stir to mix. Place dough on a floured surface and knead for about ten strokes. Too much kneading will toughen up the dough. Divide the dough in half.
  3. In a small bowl, mix together the brown sugar and cinnamon. On a floured surface, roll out 1/2 of the dough at a time to a 12x10 inch rectangle. Brush with the melted butter, and sprinkle the cinnamon mixture evenly over the dough. Cut the rectangle into 5 strips 12 x 2 inches each. Stack the strips on top of one another, and cut the stack into 2 inch squares. Place the squares, layered side down, into the muffin cups. Bake in the preheated oven for 10 to 12 minutes.
  4. In a small bowl, stir together the confectioners' sugar and milk until smooth. When cookies come out of the oven, drizzle the icing on.
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Reviews More Reviews

Most Helpful Positive Review
Oct 04, 2008

I am actually sitting here eating my new cookie and drinking a cup of tea. It is delicious. I agree that cutting them in squares is tedious so I rolled the dough out, put the sugar and cinnamon on and proceeded to make a roll just like cinnamom buns. Them I cut them in slices and put four slices together. I pinched the top half together a little and put them in my muffin pan. Next time I would use a little less flour in the dough to make it easier to roll out.

Most Helpful Critical Review
Jul 21, 2007

These taste good, like very cakey cinnamon rolls, but they aren't worth the effort --- too time-consuming for a result of only 12 cookies. I'd rather just make real cinnamon rolls.


6 Ratings

Dec 18, 2002

I wouldn't classify this as a cookie, more like mini-cinnamon buns. Very yummy.

Jul 09, 2009

It's a lot of work for very few cookies, but definately worth the effort, specially if you really want to impress someone. I've made these cookies many times now.. they're amazing.

Feb 03, 2011

Delicious! I made the recipe as written and I was very happy with the result. It's just like a cinnamon roll but without having to wait for it to rise.

Feb 03, 2010

I agree with another reviewer. . . Not quite a cookie, but not quite a cinnamon roll either. The concept was fun and the end product is good. They came out a bit "floury" for my taste. This could be due to a number of things. Flour measurements are SO critical especially depending on HOW you measure. All in all, the effort is worth it in the end.


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  • Calories
  • 531 kcal
  • 27%
  • Carbohydrates
  • 70.6 g
  • 23%
  • Cholesterol
  • 23 mg
  • 8%
  • Fat
  • 25.9 g
  • 40%
  • Fiber
  • 1.7 g
  • 7%
  • Protein
  • 5.7 g
  • 11%
  • Sodium
  • 399 mg
  • 16%

* Percent Daily Values are based on a 2,000 calorie diet.

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