Start by warming ½ cup of water until it's just warm to the touch. In a small bowl, combine the warm water with 1 teaspoon of granulated sugar and sprinkle in the packet of activated dry yeast. Let it sit for about 5-10 minutes until it becomes frothy.
In a large mixing bowl, whisk together 4 ⅔ cups of all-purpose flour and ¼ teaspoon of sea salt. Create a well in the center and add in the softened butter, room temperature eggs, vanilla extract, warm milk, and the frothy yeast mixture. Mix until well incorporated.
Add in ½ cup of crushed Oreos into your dough mixture and fold them in until evenly distributed.
Cover your dough with a clean kitchen towel or plastic wrap and let it rise in a warm place for about 1 hour or until it doubles in size.
In a medium bowl, combine softened butter, packed brown sugar, and ground cinnamon. Mix until you have a smooth paste.
Once your dough has risen, punch it down gently and roll it out into a rectangle about ½ inch thick. Spread your prepared cinnamon filling evenly over the dough, then sprinkle on another cup of crushed Oreos.
Starting from one edge, roll up your dough tightly into a log. Slice into 12 equal pieces and place them cut-side up in a greased baking dish. Cover them again with a towel while they rise for another 30 minutes.