On a Roll | Daryl Sissman’s Cinnamon-and-Chocolate Rollups Cookie Recipe

Daryl Sissman - Seacrest Country Day School Cookie ExchangeDaryl Sissman shares her recipe for Cinnamon-and-Chocolate Rollups cookies for Seacrest Country Day School‘s cookie exchange.


The cinnamon-and-chocolate rollups that Daryl Sissman bakes bring up fond memories, as she inherited the recipe from her grandma Rose. “She was always baking,” says Sissman, a first-time host and longtime baker. “She was very specific for how the dough should be cut and the right amount of chips that had to be placed perfectly on each triangle.” Sissman says it’s the heart behind this fundraiser that has made the biggest impression on her. “I’m part of this because I believe in the message and donating to the financial aid program,” she says. “The idea of community is very important to Seacrest. It’s a sense of togetherness.”

   “I’ve adapted this from my grandmother’s original recipe. Please also note the dough needs to sit overnight before baking.”


Daryl Sissman shares her recipe for Cinnamon-and-Chocolate Rollups cookies for Seacrest Country Day School's cookie exchange.Cinnamon-and-Chocolate Rollups


   For dough:

  • 1 package yeast
  • 1/4 cup of lukewarm water
  • 1tsp. and 2 Tbsp. sugar
  • 3 cups flour
  • 2 eggs
  • 2 tsp. vanilla
  • 1/2 lb. unsalted butter, melted

For assembling cookies:

  • 1 tsp. cinnamon
  • 1 cup sugar
  • Chocolate chips (nuts or raisins)


  1. Combine yeast, water and 1 tsp. sugar. Set aside.
  2. In a large bowl, mix flour, 2 Tbsp. sugar, eggs, vanilla and melted butter.
  3. Add yeast mixture to flour mixture, then refrigerate overnight.
  4. When ready to assemble, mix cinnamon with sugar.
  5. Separate dough into 4 or 5 balls.
  6. Sprinkle cinnamon and sugar mixture on a board or flat surface.
  7. Roll out each dough ball on board (as you would a pie crust), then cut into eight wedges (see diagram). There should be 32-40 wedges in total when done.
  8. Fill each wedge with chocolate chips, and roll up from wider end.
  9. Sprinkle more cinnamon and sugar, if desired.
  10. Preheat oven to 350 degrees. Place roll-ups on baking sheets, then bake 18 minutes.


Cookie photography by Vanessa Rogers

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