Prepare the yeast mixture

• In a mixing bowl, combine warm milk and granulated sugar.
• Sprinkle yeast over the top and let sit for about 5–10 minutes, until foamy (if using active dry yeast). If using instant yeast, you can skip the waiting and combine it with the flour instead.

Mix the wet ingredients

• Add the egg and melted or very soft butter to the milk mixture.
• Whisk until everything is well combined.

Add dry ingredients and make the dough

• In a separate bowl, mix flour and salt.
• Gradually stir the flour mixture into the wet ingredients using a spatula until a soft dough forms.

Knead the dough

• Turn the dough out onto a lightly floured surface.
• Knead for about 5–8 minutes, adding a little flour if needed, until the dough is smooth and elastic but still soft.
• Place the dough into a lightly greased bowl, cover, and let rise in a warm place until doubled in size.

Make the filling

• In a small bowl, stir together softened butter, brown sugar, and cinnamon until you have a spreadable paste.
• Crush the chocolate sandwich cookies into small pieces.

Shape the rolls

• Once the dough has risen, gently punch it down and place it on a lightly floured surface.
• Roll it into a rectangle (roughly ¼-inch thick).
• Spread the cinnamon-sugar butter mixture evenly over the dough.
• Sprinkle the crushed cookies evenly on top of the filling.
• Starting from the long side, roll the dough up tightly into a log.
• Slice the log into even rolls using a sharp knife.

Prepare the pan and second rise

• Line a baking pan with parchment paper.
• Arrange the rolls cut-side up in the pan, leaving a little space between them.
• Cover and let rise again until puffy.

Bake the rolls

• Preheat the oven to 350°F (about 175°C).
• Bake the rolls until golden on top and cooked through in the center. Baking time usually ranges around 20–30 minutes depending on your oven and pan.

Cool slightly

• Remove the pan from the oven and let the rolls cool on a rack for 10–15 minutes.

Make the frosting

• In a bowl, beat softened cream cheese and softened butter together until smooth and creamy.
• Add powdered sugar, vanilla extract, and a pinch of salt. Beat until thick and smooth.

Frost and garnish

• Spread the frosting over the warm rolls.
• Sprinkle extra crushed chocolate sandwich cookies on top for decoration.

Serve

• Serve warm and enjoy the soft, gooey, cookies-and-cream cinnamon rolls.