Preheat your oven to 350°F (175°C). Gather your ingredients and equipment, including a baking sheet, mixing bowl, and cast-iron skillet.

Unroll the crescent dough onto a clean surface, pinching the seams together to create one large sheet. Spread the softened butter evenly across the dough.

In a blender, combine the thawed Oregon blackberries, sugar, and vanilla extract. Blend until smooth. Spread this blackberry mixture evenly over the buttered dough.

Starting from one end, roll the dough into a log and slice it into 8-10 equal rolls. Arrange the sliced rolls in a greased cast-iron skillet.

Bake for 20-25 minutes, or until the rolls are golden brown. Drizzle any remaining blackberry filling on top before serving.

While the rolls are baking, whisk together the powdered sugar and milk until smooth. Drizzle the icing over the rolls once they have cooled slightly.