Cast iron skillet challah cinnamon rolls (Photo/Micah Siva)
Cast iron skillet challah cinnamon rolls (Photo/Micah Siva)

Turn challah dough into cast iron skillet cinnamon rolls

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If you love the taste of cinnamon rolls and you love challah, then you will love this recipe, baked to perfection in a cast iron pan and with all the sweet cinnamon goodness of a roll braided into rich challah dough. (This challah can stand on its own, but I like mine drizzled with dairy-free cream cheese frosting.) It’s also round, making it perfect for Rosh Hashanah. The mixture of cinnamon, sugar, butter and yeast means that your kitchen will smell absolutely amazing after you bake it.

While I adore challah, cinnamon rolls are the ultimate nostalgic treat. In my family, it was a tradition when I was growing up that, on our birthdays, we’d be woken up with a massive cinnamon roll for our breakfast, with a candle on top. Every time I think of cinnamon rolls, I think of my family.

Cinnamon Roll Challah

Makes 2 medium-size round challahs (in 8- or 9-inch skillets)


  • 1 package instant yeast
  • 1 Tbs. sugar
  • 1½ cups lukewarm water, divided
  • 3 large egg yolks; reserve the egg whites for brushing on top
  • ¼ cup maple syrup or honey
  • ¼ cup butter, melted
  • 1 Tbs. vanilla extract
  • 2 tsp. sea salt
  • 4½ -5 cups all purpose flour
  • 2 Tbs. coarse sanding sugar, to sprinkle before baking


  • ¼ cup butter, softened
  • ¼ cup brown sugar
  • 2 Tbs. tahini
  • 1 Tbs. cinnamon

Combine yeast, sugar and ½ cup water in a bowl of a stand mixer. Let sit for 5-10 minutes, or until the yeast starts to foam or “bloom” (if the yeast fails to bloom, it may not be fresh enough).

Add remaining water, egg yolks, honey, melted butter, vanilla and salt, mixing on low to combine.

Switch out your stand mixer paddle for a dough hook. Add flour, 1 cup at a time, mixing on low using the dough hook. Knead the dough until smooth and no longer sticky, adding more flour as needed. Transfer to a clean, oiled bowl. Cover with a clean, damp towel, and let rise until doubled in size, about 1 hour.

Preheat the oven to 350F. Line a baking tray with parchment paper or grease a 9-inch cast iron pan.

RELATED: This Rosh Hashanah, fill up on symbolic dips, bites and small plates

Punch down dough to remove any air bubbles, and transfer to a floured surface.

Cut into 6 even pieces. Roll each piece into a rope, approximately 12 inches long. Cover with a damp cloth and let rest for 10-15 minutes.

Meanwhile, make the filling by combining the butter, sugar, tahini and cinnamon.

After the dough has rested, flatten the dough strands with your fingers. Place a line of filling in the center of each strand and pinch to seal. Braid the ropes into 2 braids of 3 strands each. Coil into a circle and pinch together.

Make the egg wash: Whisk the reserved egg whites. Brush the loaf with the egg white, and top with coarse sugar (optional).

Bake in a cast iron pan or baking tray for 40 minutes, turning the tray halfway through and brushing with additional egg wash.

Serve with optional cream cheese frosting.

Micah Siva
Micah Siva

Micah Siva is a registered dietitian and trained chef in San Francisco. She develops modern Jewish recipes inspired by her grandmother, with a plant-forward twist. See her recipes and photography at Nosh with Micah.