Preheat the oven to 350°F. Arrange a rack in the middle of the oven. Lightly spray the cavities of a 24-cavity (or two 12-cavity) mini muffin pan with nonstick cooking spray.

Make the dough: In the bowl of a food processor fitted with the blade attachment, pulse the flour, sugar, and salt. Add the cold cubed butter and cream cheese and pulse until the dough comes together in one mass, about 30 to 50 one-second pulses.

Portion and press the dough: Divide the dough into 24 one-tablespoon portions (about 19g each). Use your hands to roll each portion into a ball and place a ball into each cavity of the prepared mini muffin tin. Chill the dough in the freezer for 5 minutes to firm up slightly. Use a tassie press, small measuring spoon, skinny shot glass, or your knuckle to push the dough into the cup and all the way up the side, creating a well in the center. Take care to press the dough and create wells that are deep and wide because the dough and filling will puff as they bake. Return the muffin tin to the freezer while you make the filling.

Make the filling: In a medium bowl, whisk the maple syrup, brown sugar, melted butter, granulated sugar, egg yolk, vanilla, salt, and cinnamon (if using) until combined and there are no lumps of sugar. Add the pecans and stir to coat the nuts in the maple syrup mixture.

Divide the filling and bake: Equally divide the pecan filling into each dough well, about a heaping ½ tablespoon each. Bake the cookies until puffed, the dough is golden to golden brown around the edges, and the filling is set, 25 to 30 minutes.

Cool and serve: Cool the tassies slightly in their pan set over a wire rack, about 2 minutes. Transfer the cookies directly to the rack to cool completely. If desired, very lightly dust with powdered sugar before serving. Leftover pecan pie cookies can be stored in an airtight container at room temperature for up to 5 days.