Sticky date cinnamon rolls

5 from 2 reviews

If you’re finding good dates hard to come by, will deliver them in bulk and I’ve always found them to be delicious when I’ve ordered from there. (If you want to try something other than Medjool, I love their Khadrawi and Honey dates!) And just in case you have a hankering for a full-on traditional cinnamon roll instead, see the Notes below for a standard brown sugar, butter, and cinnamon filling.


  • for the dough:
  • 1/4 cup (60 ml) milk (any kind will do)
  • 1 tsp active dry yeast
  • 2 cups (250 g) flour, plus more for rolling out
  • 3 tbsp (37 g) granulated sugar
  • 1/8 tsp salt
  • 1/4 cup (60 g) Greek yogurt (alternatively, use 1/2 cup buttermilk in place of the milk and Greek yogurt)
  • 1 large egg, room temperature
  • 1 large egg yolk, room temperature (if you like, use the egg white for an egg wash)
  • 1/2 tsp vanilla extract (my all-time favorite is this one, and Ashlae has it back in stock this morning!)
  • 3 tbsp (42 g or 1.5 oz) unsalted butter, melted
  • for the filling (see Notes for a traditional cinnamon filling):
  • 1 cup Medjool dates, pitted (about 810 dates)
  • 1 tbsp (14 g or .5 oz) unsalted butter, melted (optional)
  • 12 tbsp (1225 g) brown sugar, depending on the sweetness of your dates
  • 1 tbsp cinnamon (or more or less, to taste)
  • for the icing:
  • 1/4 cup (56 g, 2 oz, or 1/2 stick) unsalted butter, softened
  • 1/4 cup (56 g or 2 oz) cream cheese, softened
  • 1 cup (125 g) powdered sugar
  • 1/2 tsp vanilla extract
  • 2 tsp (about 15 ml) maple syrup
  • 12 tbsp (1530 ml) milk (any kind will do; optional)


  1. The night before: For the dough, heat the milk in a Pyrex measuring cup or a small bowl until just warm to the touch (about 110 F or less) and sprinkle the yeast over top. Set aside for about five minutes, or until foamy on top. (See Notes if yours is having trouble foaming.) Meanwhile, whisk together the flour, sugar, and salt in a separate, large bowl.
  2. When the yeast is foamy, add the yogurt, egg, egg yolk, vanilla extract, and melted butter to the yeast-milk mixture and whisk to combine. (If you like, you can save the egg white and use it as a quick egg wash before you bake the rolls.)
  3. Add the wet ingredients to the dry, then mix with a wooden spoon or rubber spatula until all the flour is incorporated and a wet, sticky dough forms. Knead in the bowl for 5-6 minutes. The dough will be very wet — the looser and stickier the dough is now, the fluffier and softer the rolls will be later, so don’t worry if it seems gloppy, and try not to add too much flour as you knead. If kneading with your hands, you can add a bit of flour as necessary to keep from sticking, but I just kneaded it by folding it in on itself with a large rubber spatula, which did the trick just fine and kept things from getting frustrating. When the dough begins to look a bit smoother and more elastic, cover with plastic wrap or a damp cloth and place it in the refrigerator to rise overnight. (Alternatively, you can let the dough rise at room temperature for about 2 hours, or until well-doubled — I prefer overnight to allow the flavor and gluten to develop more fully, and because a cold dough is much easier to work with, especially a delicate one like this.)
  4. The night before or the day of: For the filling, bring a cup or so of water to boil in a kettle or small pot. Pour enough boiling water over the dates to fully submerge them, and let soak until soft, about 10 minutes. Drain the water, then add the dates to a food processor or blender. Add the melted butter, brown sugar, and cinnamon, then process until smooth. You may need to scrape down the sides once or twice. Set aside until ready to use, or, if made the night before, refrigerate.
  5. The day of: Generously flour a work surface and scrape the still-cold dough onto it. (No need to let the refrigerated dough come to room temperature. It will warm during the second rise, and I find that a cold dough is much easier to roll and work with.) Roll the dough out to a large rectangle, about 10”x13” or thereabouts, and about 1/4″ in thickness. Spread the date mixture across the dough, leaving a 1/2″ border around the edges. Gently but tightly roll the rectangle into a log. Rolling the rectangle width-wise will give you larger cinnamon rolls with more swirls; length-wise, smaller. Either way, pinch the seam shut and place the log seam-side down.
  6. Using unflavored dental floss or a serrated knife, gently slice the log into about 8 to 10 rolls, a little more than an inch in width. If using a knife, cut by gently moving the knife back and forth in a sawing motion to avoid pressing down on the dough — that should help it keep its shape. It’s important to use a serrated knife rather than a smooth-edged one.
  7. Place the rolls, cut-side down, into a 9-inch pie plate or cast-iron skillet, or an 8×8-inch square baking dish. Leave some space for them to expand; if you run out of room, bake the extras in individual ramekins or free-form on a baking sheet. Cover loosely with plastic wrap or a damp towel and let rise for about 45 minutes to an hour, or until rolls are almost doubled again. (If you like, you can do an overnight rise in the refrigerator at this point as well, or even freeze the rolls, well-wrapped. Either way, just bring the rolls to room temperature before baking. See Notes below for a Christmas schedule!)
  8. About 30 minutes before you’re ready to bake, preheat the oven to 350 F. When the rolls are nearly doubled, brush them with the remaining egg white, if you like, then bake about 18-22 minutes, or until rolls are just barely golden in spots — this will ensure that they’re still nice and soft in the center. If using a cast-iron pan, you may want to take them out a minute or two earlier, since the pan retains heat so well and will continue to cook the rolls for a bit afterwards.
  9. While the rolls cool, make the frosting. Using an electric mixer or plenty of arm strength, beat the butter and cream cheese together until smooth. Add the confectioners’ sugar in batches, beating vigorously after each addition until smooth. Finally, add the vanilla and the maple syrup and beat again to incorporate. If you want more of a glaze than a frosting, add the milk, a tablespoon at a time, until it reaches your desired consistency. I added about 2 tablespoons. Spread over the rolls while still slightly warm to let the frosting melt into the crags, and enjoy immediately.


For a traditional cinnamon filling, use 4 tbsp (1/4 cup, 2 oz or 1/2 stick) softened butter, 1/2 cup packed brown sugar, and 1 tbsp cinnamon. Spread the butter over the dough, then sprinkle the brown sugar and the cinnamon evenly over top.

If your milk is having trouble foaming and your yeast is fresh, it might be because the milk needs scalding first. Heat the milk until it just bubbles at the edges but does not boil, then cool until just warm to the touch. Add the yeast and see if it foams this time, then proceed as normal.

For Christmas: If you’d like to bake these first thing in the morning on Christmas Day, here’s what I’d do!

10 AM, Christmas Eve: Make the dough on Christmas Eve morning around 10 AM. Let rise in the refrigerator for 8-10 hours, or until doubled.

8 PM, Christmas Eve: On Christmas Eve … eve, make the filling, roll out the cold dough, shape, cut, and place into the baking pan or skillet. Let rise in the refrigerator again, covered well, this time overnight.

Christmas Day: On Christmas morning, let the rolls sit at room temperature for about 15-20 minutes while the oven preheats, then bake as directed, make the frosting while they bake, and enjoy warm, with a side of presents. 🙂