Prep the rolls first. The milk needs to be between 110°F and 115°F. Typically, ½ cup of milk microwaved for 20-30 seconds will get it to desired temp. Whisk active dry yeast into warm milk. Let it dissolve.
Pour the instant yeast mixture into the bowl of a stand mixer with the softened butter & sugar. With the paddle attachment, mix on medium speed.
Ensuring the mixture is no longer warm, add the egg and orange zest.
Transition to the dough hook attachment and gradually add flour & salt into the bowl and fold together until a dough forms. The dough ingredients will be sticky—that's OK.
Remove the dough from the bowl. Then, knead it on a floured surface for 6-8 minutes.
Grab a clean mixing bowl and spray with cooking spray. Then, place the kneaded dough in the greased bowl, cover with a linen towel or plastic wrap, and let rise for 1-2 hours in a warm place.
After the dough has risen (about 3-4x in size), it's time to punch it down and roll it out. Flour your surface once more. Using a rolling pin, glass jar, or wine bottle, flatten the risen dough until it's about ¼" thick on the lightly floured surface. It shouldn't be thin enough that you can see through, but should be thin enough to roll.
Next, make the filling: heat a sauce pot to medium heat. Combine cranberries, orange juice, orange extract, and sugar. Stir together.
The cranberries will start to pop and jam like texture will form. Continue stirring
Using a rubber spatula, spread the cranberry filling evenly across your dough leaving ~½ an inch on the border so juices don’t spill out too much and burn.
Then, starting at the end of your dough, begin to carefully roll it into a log shape.
Then, using a serrated knife (or unflavored floss! See Pro Tip below), slice the rolled dough into 12 cinnamon rolls.
Now, let's get ready to bake. Preheat the oven to 350°F and layer a 9x13 baking pan with parchment paper. Then, spray with cooking spray.
Place Cinnamon Rolls into the prepared pan and bake for 22-26 minutes until outside of the dough starts to turn golden brown.
While the rolls bake, let's make the glaze. Gather all ingredients into a mixing bowl and beat until smooth.
Once your Cranberry Cinnamon Rolls are done baking, top with glaze and enjoy!