In a small heatproof bowl, stir together the softened butter, dark brown sugar, and ground cinnamon until smooth and uniform. Transfer the mixture into a ziplock bag or piping bag, snip a tiny corner off the tip, and set aside at room temperature so it stays pliable.

In a medium bowl, beat the softened cream cheese and butter until smooth and lump-free. Gradually whisk in the powdered sugar, vanilla extract, and warm milk until silky and pourable. Cover and keep warm.

In a large mixing bowl, whisk together the flour, sugar, baking powder, baking soda, and salt. In a separate bowl, whisk buttermilk, eggs, melted butter, and vanilla. Pour wet ingredients into dry and gently fold just until combined; small lumps are totally normal and make pancakes extra fluffy!

Heat a large nonstick skillet or cast-iron griddle over medium-low heat and grease lightly with butter. Pour 1/3 cup of batter per pancake. As small bubbles start forming on the surface (about 1 to 2 minutes), quickly pipe a spiral of cinnamon swirl paste starting from the center outward toward the edge.

Carefully slide a thin spatula underneath and flip the pancake in one confident motion. Cook for an additional 1.5 to 2 minutes on the cinnamon side over gentle heat so the sugar caramelizes into the batter without scorching. Wipe the pan clean between batches.

Stack the golden cinnamon-swirled pancakes high on warm plates and generously drizzle with warm cream cheese glaze. Serve immediately while hot and fluffy!