Gooey Gloppy Cinnamon Rolls

“Gooey, gloppy, cinnamon rolls are so hard to resist. The rolls are baked in a syrup. When they are done, the rolls rest in the pan for a few minutes to allow the syrup to set, then they are turned upside-down onto a plate where the syrup becomes the glaze. They’re sinfully delicious.” (my Mom’s note from the Oppenneer Family Cookbook).

Terribly uninformative video involving Gooey Gloppy Cinnamon Rolls

Today was a perfectly dreary autumn day, colorless and rainy. Becca was binge watching Gossip Girls so I headed into the kitchen to make some feel-good food. This is a special recipe – you won’t find it in any of my Mom’s commercially available cookbooks. She put this recipe in The Oppenneer Family Cookbook, a loose-leaf limited-release volume containing all of the recipes our family grew up on and more.

The glaze (or syrup as Mom calls it) is the secret weapon of this recipe. It seeps into the spirals and turns into actual cocaine. That last sentence was just to see if you were awake. But really, the glaze is part of what makes these rolls so addictive.

So many of the implements in my kitchen were once used by my Mom in her kitchen. For this recipe, I was able to use her old rolling pin.

I like to imagine it as being very old, perhaps old enough to have been carried across the prairie by a salty pioneer woman who used it to protect her family from an aggressive bear or perhaps a wild boar. I guess what I’m trying to say is that I feel history when I hold it in my hands – a rugged old-world quality that makes me write paragraphs like this one.

Cinnamon is the Chuck Norris of spices. If you don’t give it the respect it deserves, it will kick your ass. That’s why it is used in serious foodstuffs like Fireball (you know, the liquor that you smuggle onto the bleachers for every fall sport your kid plays), Red Hots (so named for the effect of eating too many of them), and others.

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Once you flip the rolls over, you will see that they are drenched in the glaze that was on the bottom of the dish. This is a perfectly suitable place to end the recipe. But, hell no. Because without the icing, the rolls will only give you half a heart attack. Having second thoughts about pouring more sugar over the sugar in this sweet bread? Well don’t be a sissy. Take a moment to gather yourself… and pour that sugar on the sugar, baby.

Gooey Gloppy Cinnamon Rolls

Gooey, gloppy, cinnamon rolls are so hard to resist. The rolls are baked in a syrup. When they are done, the rolls rest in the pan for a few minutes to allow the syrup to set, then they are turned upside-down onto a plate where the syrup becomes the glaze. They're sinfully delicious.
Prep Time 2 hours 30 minutes
Cook Time 25 minutes
Total Time 2 hours 55 minutes
Servings 16 large rolls
Author Betsy Oppenneer


For the bread

  • 1 scant tablespoon (or 1¼-ounce package) active dry yeast
  • cups warm water about 110 degrees
  • 1 cup warm milk about 110 degrees
  • 3 tablespoons vegetable shortening
  • 2 large eggs
  • ¼ cup granulated sugar
  • 1 teaspoon salt
  • 3½ to 4½ cups unbleached flour

For the glaze

  • 2 tablespoons butter
  • ¾ cup firmly packed brown sugar
  • ½ cup light corn syrup

For the filling

  • 4 tablespoons melted butter
  • 1 tablespoon cinnamon
  • ¾ cup firmly packed brown sugar

For the icing

  • ½ cup butter softened
  • 1 teaspoon vanilla extract
  • 2 cups confectioners' sugar sifted
  • 2 tablespoons milk


  1. In a large bowl, stir the yeast into water to soften.
  2. Add milk, vegetable shortening, eggs, sugar, salt, and 2 cups flour to the yeast. Beat vigorously for 2 minutes.
  3. Gradually add flour, ¼ cup at a time, until the dough begins to pull away from the side of the bowl. Turn the dough out onto a floured work surface.
  4. Knead, adding flour a little at a time, until you have a smooth, elastic dough.
  5. Put the dough in an oiled bowl. Turn to coat the entire ball of dough with oil. Cover with a tightly woven towel and let rise until doubled, about one hour.
  6. While the dough is rising, prepare the syrup by melting 2 tablespoons of the butter in a small saucepan. Add ¾ cup brown sugar and the corn syrup and stir to combine. Over medium heat, bring the mixture to a boil. Immediately remove from the heat and divide evenly into two well-seasoned 9-inch round pans. Set aside.
  7. Turn the dough out onto a lightly oiled work surface and roll into an 18 by 24-inch rectangle. Brush with melted butter for filling. Leave ½ inch along one of the short edges with no butter or filling to make it easier to seal after rolling. Sprinkle the dough with cinnamon and brown sugar. Roll the dough toward the unfinished edge to form an 18-inch cylinder. Pinch the loose edge to the cylinder.
  8. Cut the cylinder into 16 equal pieces (they'll be a little over an inch wide). I find the best way to cut rolled breads so they keep their shape is with plain, unwaxed, dental floss. Cut off a piece of floss about 14 inches long. Wrap the floss around the index finger on both hands. Pull the floss taut. Lightly score the top of the cylinder with the floss so you know where to cut the rolls. Slip the floss under the roll where it is scored. Bring the ends of the floss up, cross them, and pull straight out to the sides. Presto, the perfect cut. Place 8 rolls in each pan on top of the syrup with the cut side up.
  9. Cover with a towel and let rise until almost doubled, about 50 minutes.
  10. Preheat the oven to 350 degrees.

  11. Bake for 25 minutes, or until the internal temperature of the rolls reaches 190 degrees

  12. Let the rolls cool in the pan for 3 minutes. Invert onto a plate or foil. Leave the pan covering the rolls for another 2 minutes then remove the pan.

  13. Once the rolls have cooled, mix all of the icing ingredients together and drizzle it over the rolls.

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