Start by making the cheesecake filling since it needs time to firm up. Beat the softened cream cheese (make sure it’s really soft, or you’ll get lumps) with 1/4 cup sugar and vanilla until it’s smooth and creamy – about 2 minutes. Scrape it into a bowl and pop it in the fridge while you make the cookie dough.

Beat in the pumpkin puree, egg, and vanilla. The mixture might look a bit curdled – that’s totally normal with pumpkin cookies. Keep mixing until it’s well combined.

Gradually stir in your dry ingredients until just combined. The dough will be pretty soft and slightly sticky – that’s exactly what you want. Pop it in the fridge for about 30 minutes so it’s easier to handle.

While the dough chills, mix your cinnamon sugar coating in a shallow bowl and preheat your oven to 350°F. Line your baking sheets with parchment – these cookies can stick a bit otherwise.

Here’s the fun part: scoop out about 2 tablespoons of cookie dough and flatten it in your palm. Make a little indent in the center, add about 1 teaspoon of the cold cream cheese mixture, then fold the dough around it, sealing well. Roll into a ball, then coat in the cinnamon sugar mixture.

Place the cookies about 2 inches apart on your baking sheets – they’ll spread a bit. I usually get 8-9 cookies per sheet.

Bake for 12-14 minutes, rotating the pan halfway through. You’ll know they’re done when the edges are set but the centers still look slightly soft – they’ll continue setting up as they cool. The bottoms should be just barely golden brown.

Let them cool on the baking sheet for 5 minutes (they’re too soft to move right away), then transfer to a wire rack to cool completely.