In a small saucepan over low heat, warm 1 cup of milk and 5 tablespoons of butter until the butter has melted and the temperature reaches 105 F to 115 F on a thermometer.
Pour the mixture into the bowl of a stand mixer and sprinkle the yeast on top without stirring it in.
Let it sit until it foams for 8 to 10 minutes.
Using a wooden spoon, stir in the sugar and salt.
Add 2 ½ cups of flour and using a dough hook attachment, mix on low until just combined, about 30 seconds.
Add the eggs and mix on low until completely incorporated for another 30 seconds, scraping down the sides as needed.
Then, beat on medium-high speed for 2 to 3 minutes until a smooth batter forms.
Remove the bowl from the stand mixer and stir in the remaining 2 ¼ cups of flour, mixing for 3 to 4 minutes until the dough comes together and forms a tacky ball.
Transfer the dough ball to a floured surface and knead it for 3 to 4 minutes until it is smooth and elastic, adding more flour as needed if the dough is wet.
Wipe the mixing bowl clean then coat it with the canola oil.
Add the dough ball, turning it once to grease the surface of the dough.
Cover the bowl with plastic wrap and let the dough rise in a warm place for 50 minutes to 1 hour until it doubles in size.
While the dough is rising, make the filling. In a medium bowl, stir together 8 tablespoons of softened butter, 1 ½ cups of light brown sugar, 2 tablespoons of all-purpose flour, 1 tablespoon of ground cinnamon, and ½ teaspoon of kosher salt, forming a granular paste. Set it aside.
Grease a 9x13-inch pan with butter and set it aside.
When the dough is ready, roll it out onto a floured surface into a 12x18-inch rectangle that is ¼-inch thick.
Spread the filling over the dough, leaving a 1-inch border on all sides.
Starting at one long end, roll the dough into a log.
Pinch to seal the long seam and place the log onto a lightly floured surface, seam-side down.
Using a large serrated knife, cut the log into 14 pieces, each about 1 ½-inches thick, and place them in the prepared pan, cut side up.
Loosely cover the pan with plastic wrap and let it sit in a warm place for a second rise until the rolls are puffy or around 20 to 25 minutes.
Position a rack in the center of the oven and preheat it to 375 F.
After the second rise, remove the plastic and bake the rolls for 18 to 22 minutes until golden brown.
Meanwhile, in a small saucepan combine ⅔ cup of granulated sugar, 2 tablespoons of light brown sugar, 4 tablespoons of butter, and ⅓ cup of whole milk, and place it over medium heat.
Cook for 2 to 3 minutes, whisking constantly until the butter has melted and the sugars have dissolved.
Remove the cinnamon rolls from the oven when they are done and let them cool for 10 minutes.
Drizzle the glaze over top.
Let the rolls cool for at least 20 minutes before eating.