In a small bowl, whisk together the melted butter, packed dark brown sugar, and ground cinnamon until smooth and creamy. Transfer the cinnamon mixture to a squeeze bottle or a zip-top plastic bag with a tiny corner snipped off. Set aside at room temperature so it remains soft and pipable.

In a medium bowl, beat the softened cream cheese and butter with an electric hand mixer or whisk until completely smooth. Gradually whisk in powdered sugar, vanilla extract, and milk until a silky, pourable glaze forms. Set aside.

In a large bowl, whisk together flour, granulated sugar, baking powder, baking soda, and salt.

In a separate bowl, whisk together buttermilk, eggs, melted butter, and vanilla extract.

Pour wet ingredients into dry ingredients. Fold gently with a spatula just until combined—small lumps are totally fine! Let batter rest for 5 to 10 minutes to allow the baking soda and buttermilk to activate fluffy air pockets.

Heat a large non-stick skillet or griddle over medium-low heat (about 325°F / 165°C). Lightly grease with butter or cooking spray.

Pour 1/3 cup of batter per pancake onto the griddle. Starting in the center of each pancake, gently pipe the cinnamon swirl in a spiral toward the outer edge (leave a 1/2-inch border clean so it does not spill onto the pan).

Cook for 2 to 3 minutes until bubbles form across the surface and pop, and the edges look set. Carefully slide a wide thin spatula underneath and flip the pancake in one decisive, gentle motion.

Cook for another 1 to 2 minutes on the swirl side. The cinnamon sugar will caramelize into a delicious, candy-like crust. Wipe the pan clean between batches with a paper towel if any caramelized sugar sticks.

Stack the warm pancakes high on a plate, drizzle generously with warm cream cheese glaze, and serve immediately!