Pulse the flour, sugar, salt, and butter in a food processor. Drizzle in the milk or whipping cream, 1 tablespoon at a time, until the dough comes together and clumps easily.
Divide the dough into two discs and wrap them in plastic and set aside while you make the filling.
For the filling, mix the cinnamon, sugar, butter, maple syrup, and flour together.
Lightly flour your work surface and have more flour on hand for dusting the rolling pin.
Roll out one of the discs to a large rectangle, about 8 x 10. The dough will be fairly thin.
Sprinkle half the cinnamon sugar mixture over the dough, then starting with the long edge nearest you, roll it up jelly roll-style.
Repeat with the remaining dough and cinnamon sugar.
Wrap the rolls in plastic wrap and refrigerate them for 2 hours or overnight.
Preheat the oven to 350-F.
Thinly slice (about 1/4-inch thick) rounds from the cold log of dough. Lay them on a parchment-paper lined sheet pan, about 1-inch apart.
Bake at 350-F for about 12-15 minutes or just until the edges start to look golden brown. Leave the Cinnamon Roll Cookies to cool on the sheet pan.