How to Make It
Roll and knead your dough. Combine water and sugar in a medium bowl. Sprinkle yeast over top and set aside until foamy, about 5 minutes. Add 4 cups flour and salt, and stir with a wooden spoon until a shaggy dough forms. Turn out onto a lightly floured surface and knead until dough comes together, about 10 times. Lightly oil a medium-sized bowl. Add dough and turn to coat. Cover with plastic wrap and set aside until doubled in size, about 90 minutes.
Prepare the topping. Meanwhile, combine brown sugar, butter, and maple syrup in a 10-inch skillet, preferably cast-iron. Cook, stirring often, until sugar dissolves and mixture is evenly bubbling across the surface, 2 to 3 minutes. Let cool slightly, then sprinkle with nuts. Set aside. If you don’t have a 10-inch skillet, you can do this in whatever skillet you have and then swiftly transfer the toffee mixture to a 10-inch cake pan.)
Fill and assemble. Preheat oven to 350°F. Combine butter, dates, brown sugar, and salt in a medium saucepan and place over medium-high heat. Cook, stirring often, until butter melts. Continue to cook, stirring and mashing to help break up dates, until mixture comes to a boil and dates are broken down, about 4 minutes. Let cool to room temperature.
Once the dough has doubled in size, turn out onto a lightly floured surface. Divide dough in half (this will make it easier to work with) and working with one at a time, roll each piece into a 12- by 16-inch rectangle. Divide date mixture between the two pieces of dough, spreading all the way to the edges. Sprinkle each piece evenly with 2 teaspoons cinnamon. Starting from the long end, roll up dough and place seam-side down. Cut dough crosswise into 2-inch spirals. Transfer rolls, cut sides down, to prepared skillet or cake pan, arranging snugly to fit. Bake until golden and risen, 30 to 35 minutes. Let cool 5 minutes before inverting onto a rack. Let cool slightly before eating.