Preheat oven to 350°F. In a 9×13 inch baking dish, add brown sugar, butter, and water. Place in preheating oven to melt, about 5 minutes.
In a small bowl, combine brown sugar and cinnamon. Mix well and set aside.
In a large mixing bowl, whisk together flour, sugar, salt, and baking powder until evenly combined.
Add 1 cup milk to dry ingredients and stir until soft dough forms, similar to biscuit dough. Add additional milk 1 tablespoon at a time if needed, up to 1/4 cup.
Remove baking dish from oven. Gently stir butter, water, and sugar together with a fork to create smooth syrup base. Set aside.
Turn dough onto well-floured surface. Pat and roll into a 12×14 inch rectangle. Don’t overwork the dough.
Spread softened butter evenly over dough, leaving 1/2 inch border. Sprinkle cinnamon sugar mixture evenly over buttered dough.
Starting with long end, gently roll up dough into tight log. Pinch seam closed.
Using sharp knife, cut log into 12 equal pieces, each about 1 inch thick. Wipe knife between cuts for cleaner slices.
Place 12 pieces cut side down in prepared baking dish with caramel. Arrange in 3 rows of 4 rolls, spacing slightly apart.
Bake for 20-25 minutes until lightly golden and baked through, especially where rolls touch and in center. Toothpick should come out clean.
Immediately turn pan upside down onto large serving platter. Let sit 30 seconds for caramel to drip, then lift pan off. Drizzle remaining caramel over rolls. Serve warm.
Notes
Use real butter for best flavor. Fresh baking powder is essential for proper rise.
Work quickly after adding milk – baking powder activates immediately. Don’t overwork dough or rolls will be tough.
Always flip immediately after baking so caramel stays soft. Can freeze unbaked rolls for up to 1 month.