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Warm the milk over on the stove over low heat or microwave it until lukewarm. No need to use a thermometer, but to be precise: about 95°F (35°C). Pour the warm milk into the bowl of a stand mixer fitted with the dough hook or paddle attachment (OR you can use a handheld mixer). Whisk in the yeast and 1 teaspoon granulated sugar. Cover with a clean towel and let sit until the yeast is foamy, about 5-10 minutes. This is called proofing the yeast. If the yeast does not dissolve and foam, start over with fresh active yeast. On low speed, beat in the remaining 1/4 cup sugar, salt, butter, egg, and 2 cups of flour until combined. The dough will be wet. While continuing to beat on low speed, add the remaining flour 1/4 cup at a time until a soft dough forms. Dough will be ready when it gently pulls away from the sides of the bowl. I usually use 2 and 3/4 cups flour total. **If you do not have a mixer, you can stir the dough by hand with a wooden spoon in this step.
Turn the dough out onto a lightly floured surface, then knead for 1 minute. Let the dough rest for about 10 minutes. During this 10 minutes, line a 4 or 5 quart slow cooker with greased parchment paper. (I spray it with non-stick spray, but brushing oil or softened butter all over it works too.) If you have a larger slow cooker, that’s ok– just space the rolls out more.
After 10 minutes, roll the dough out in a 14×8 inch rectangle. Spread the softened butter on top. Mix the cinnamon and sugar together, then sprinkle on top of the butter. Roll the dough up tightly, then cut into 10-12 even pieces and place them inside the lined slow cooker. Place a paper towel right under the lid of the slow cooker– this will help keep condensation off of the cooking rolls. Do not leave that step out and do not use a cloth towel.
Turn your slow cooker on high speed and cook for 2 hours, or until the rolls are fully cooked through. It’s usually 2 hours, sometimes 2 hours and 15 minutes. Once they’re done, remove the rolls from the cooker right away by lifting out the parchment paper.
Right before serving, top your cinnamon rolls with glaze. Whisk the confectioners’ sugar, maple syrup, and milk together until smooth. Add a little more milk if too thick. Drizzle over the warm rolls.
Rolls are best enjoyed the same day, but stay fresh covered tightly in the refrigerator for 5 days. Rolls (with or without icing) freeze well up to 3 months. Thaw overnight in the refrigerator and heat up however you prefer.