Prepare the Dough:

• In a small bowl, dissolve the yeast in warm milk with 1 tablespoon of sugar. Let it sit for 5–10 minutes until foamy.
• In a large bowl, combine the flour, remaining sugar, and salt. Add the yeast mixture, melted butter, and egg. Mix until a dough forms, then knead on a lightly floured surface for about 5–7 minutes until smooth and elastic.
• Place the dough in a greased bowl, cover, and let it rise in a warm spot for about 1 hour, or until doubled in size.

Make the Filling:

• In a medium bowl, beat the softened butter, brown sugar, and cinnamon until well combined.
• Gently fold in the crushed Oreos.

Assemble the Rolls:

• Punch down the risen dough and roll it out on a lightly floured surface into a 12×16-inch rectangle.
• Spread the butter-sugar-cinnamon mixture evenly over the dough.
• Starting from the long edge, roll up the dough tightly into a log. Using a sharp knife, cut the log into 12 even slices.
• Place the rolls into a greased 9×13-inch baking dish. Cover and let them rise for an additional 30 minutes.

Bake:

• Preheat your oven to 350°F (175°C).
• Bake the rolls for 20–25 minutes, or until golden brown and cooked through.

Prepare the Icing:

• While the rolls bake, whisk together the powdered sugar, milk, and vanilla extract until smooth.

Finish & Serve:

• Drizzle the icing over the warm rolls before serving.