Challah Dough Pistachio Rolls with Blood Orange Glaze

Challah Dough Pistachio Rolls with Blood Orange Glaze

My friend Ariel Zipkin-Weiss makes my favorite challah - it’s a parve challah but it’s so rich and moist that you’d never guess. I like it so much that I’ve started using it as a base for all kinds of things, including cinnamon rolls. The cinnamon roll is bizarre in its orthodoxy. While donuts have been made into every flavor and shape under the sun, and bagels have been turned into a bad acid trip for some reason, the cinnamon roll remains in its original form.Using Ariel’s challah dough as a starting point, I wanted to reimagine the roll as a baklava, so I kept the basic approach to making a cinnamon roll filling but swapped out the ingredients to give it a baklava flavor - pecans became a mix of walnuts and pistachios, cloves were added to the cinnamon, and honey took the place of maple syrup. At first I tried topping them with honey and a bit of sea salt but they were already sweet enough. I love blood oranges and found them to be a nice, slightly tart addition to the rolls - the acidity gave another dimension to the flavor and looked beautiful with the pistachio dust. Also, it’s nice to have some seasonal recipes to look forward to during winter in Chicago.

Freshly glazed and ready to devour.

Freshly glazed and ready to devour.

Makes about 24 rolls.
Time: about 4 to 5 hours total, about 25 minutes active work
Special Equipment: food processor, rolling pin, zesting tool - a Microplane is nice but not vital


1 ⅓ cups warm water
1 tablespoon active dry yeast
5 cups and a half cups bread flour, plus more for dusting
⅔ cup plus 2 teaspoons white sugar, separated
4 large eggs (1 is for the egg wash)
½ cup canola oil
½ tablespoon kosher salt


½ cup honey
2 sticks room temperature unsalted butter
½ cup pistachio pieces, plus ¼ cup for dusting
½ cup walnut pieces
½ cup brown sugar, packed
½ cup all purpose flour
2 tablespoons ground cinnamon
⅛ teaspoon ground cloves
1 tablespoon kosher salt


3 cups powdered sugar
Zest of 2 blood oranges
Juice of 2 blood oranges (about 4 tablespoons)
Cooking spray



Pour the water into a small bowl, add the yeast and 2 teaspoons of sugar and stir to dissolve. Let rest until the yeast has begun to bubble, about 5 to 10 minutes.

While you wait, thoroughly mix the dry ingredients in a large mixing bowl, forming a well in the center once they’re well combined.

Next, pour the yeast mixture into the well, followed by the eggs and oil.

Use a wooden spoon or rubber spatula to mix the dough until it’s all combined. Next, knead the dough on a well-floured surface until it looks smooth and feels nice and elastic, about 7 to 10 minutes.

Place the dough in a lightly oiled bowl, cover it tightly with plastic wrap or a damp towel. Let it rise until doubled in size - about 1 ½ to 2 hours. A cool kitchen will make for a longer rise time, but wait until the challah is soft to the touch and quite airy. The state of the dough warrants more attention than the clock.

While the dough rises, make the filling. Place all of the filling ingredients in a food processor and run it until a smooth paste forms - about 3 minutes.

Next, make the glaze. Begin by zesting each of the oranges over a medium sized mixing bowl. Then, juice both of the oranges over the bowl, add the sugar, and whisk until well-combined. The glaze should not be thick like a frosting, but should drip off the whisk more slowly than water. Make adjustments as needed, adding juice, water, or sugar to improve the consistency.

Once dough has doubled, gently punch it down and divide it into 2 equal-sized pieces.

Line two baking sheets with parchment paper and grease it with butter or cooking spray.

Add a light dusting of flour to your work surface and prepare the first piece of dough. Use your hands to gently shape it into a rectangle, then roll it out to about the size of a baking sheet, with the wider side parallel to you. Spread half of the filling mixture evenly across the rectangle, leaving about two inches bare on the far side, and coming up nearly to the edges on the others.

In a small bowl, beat the remaining egg to make the egg wash and gently brush some onto the far edge of the dough.

Starting at the side that is closest to you, roll the dough into a fairly tight log, gently pressing at the seam and rolling it back and forth to seal it.

Use a sharp knife to gently cut the log into slices about 1-inch thick. Place rolls about an inch apart and cover them with plastic wrap. Repeat the process with the second piece of dough. Let the rolls rise until puffy and nearly touching, about 1 hour.

Preheat the oven to 350°F and bake rolls for 8 minutes, rotate them, then bake for about 9 more minutes - till the tops begin to turn a bit golden brown.

Let the rolls cool for about 20 minutes, then glaze them by gently placing each one in the glaze and tossing on a dusting of pistachios while it’s still wet. Glaze takes about 30 minutes to set. They might be messy and in fact they should be.