Preheat your oven to 350°F.
Add the granulated sugar to a saucepan over medium heat. Cook until the sugar melts completely and turns a beautiful amber caramel color. Keep a close eye on it so it doesn't burn.
As soon as the sugar has melted and turned caramel-colored, remove it from the heat and immediately pour it into a 9-inch round cake pan. Work quickly, tilting the pan to coat the entire bottom evenly. The caramel thickens and hardens very fast.
Add the softened cream cheese, eggs, vanilla extract, cinnamon, pumpkin puree, evaporated milk, and sweetened condensed milk to a blender. Blend just until smooth and combined. Don't overmix! A quick blend is all you need.
Pour the flan mixture through a fine-mesh sieve directly into the caramel-coated cake pan. This helps remove any lumps and gives the flan a smoother texture.
Cover the cake pan tightly with aluminum foil. Place it inside a larger roasting pan and carefully pour hot water into the roasting pan until it reaches about halfway up the sides of the cake pan.
Carefully transfer to the oven and bake for 1 hour and 10–15 minutes, or until the edges are set and the center has a slight jiggle.
Remove the flan from the water bath and let it cool at room temperature until cooled and remove the aluminum foil.
Refrigerate for at least 4 hours, preferably overnight, so the flan can fully set.
When ready to serve, run a thin knife around the edges of the cake pan to loosen the flan. Place an 11-inch serving plate or platter over the pan and carefully invert it. Allow the caramel sauce to drizzle over the top, slice, and enjoy!