In a small bowl, dissolve 1 teaspoon of the granulated sugar into the ½ cup of warm water. Sprinkle the yeast over the top and let it sit undisturbed for 5 to 7 minutes until it becomes frothy and activates.
In the bowl of a stand mixer fitted with the dough hook, combine the activated yeast mixture, warm milk, the remaining granulated sugar, the whole egg, and the egg yolk. Whisk briefly by hand to break up the eggs.
Add the kosher salt and 2 cups of the all-purpose flour to the wet base. Turn the mixer to low speed and let the hook incorporate the flour.
While the mixer is running, add the 5 tablespoons of softened cubed butter one piece at a time. Once the butter is absorbed, add the remaining flour and exactly ½ cup of the finely crushed cookie crumbs.
Knead on medium-low speed for 5 to 7 minutes until the dough turns smooth, elastic, and pulls away completely from the sides of the bowl.
Shape the sticky dough into a ball and place it inside a lightly greased bowl. Cover tightly with plastic wrap and let it rise in a warm, draft-free spot for 1 hour, or until it has completely doubled in volume.
Punch down the risen dough and turn it out onto a lightly floured countertop. Use a rolling pin to shape the dough into a large 14×20-inch rectangle of uniform thickness.
Using an offset spatula, spread the ⅓ cup of soft filling butter evenly across the surface of the dough, leaving a clear ½-inch border along the top edge.
In a small bowl, mix the brown sugar and ground cinnamon together. Sprinkle this spice mixture uniformly over the buttered dough, and top it with 1 full cup of the crushed cookie crumbs. Gently press the crumbs down into the butter so they adhere firmly.
Starting from the long edge closest to you, roll the dough upward tightly into a solid log. Use a piece of unflavored dental floss or a sharp serrated knife to slice the log into 12 equal portions.
Arrange the sliced rolls cut-side up in a greased 9×13-inch baking dish. Cover with a clean kitchen towel and let them rise a second time for 30 to 40 minutes until puffed up and touching each other. Meanwhile, preheat your oven to 350°F.
Bake uncovered at 350°F for 28 to 32 minutes until the tops look beautifully golden brown and set. Remove the pan from the oven and let the rolls cool down flat on a wire rack for 5 minutes.
While the rolls take a brief rest, assemble the frosting. Beat the softened cream cheese and ¼ cup of butter together with an electric hand mixer for 2 minutes until completely smooth. Slowly add the sifted powdered sugar and vanilla extract, whipping until light and fluffy. Add heavy cream a splash at a time if you prefer a pourable glaze consistency.
Slather the rich cream cheese frosting generously over the warm rolls, allowing it to melt down into the spirals. Garnish the surface with the remaining ½ cup of roughly chopped cookie pieces for an awesome textural crunch, and serve warm.