Make the syrup. Add all the syrup ingredients (orange juice, water, sugar, orange zest, and cinnamon stick) to a small pot and bring to a boil. Simmer for about 5-7 minutes. Set it aside to cool.
Bunch up the filo accordion-style and add it to a baking tray.
Preheat the oven to 210°F (100°C) and dehydrate the filo for about an hour until the filo is dried out. Take it out and set it aside to cool for a few minutes.
Make the batter for the portokalopita. To start, in a bowl, beat the eggs with sugar with a hand mixer for about 8-10 minutes.
Add the orange zest, oil, vanilla, yogurt, baking powder, and soda, and mix for 10 seconds.
Using your hands, break down the phyllo/filo.
Add the broken filo to the batter, in 4-5 batches, mixing lightly after every batch with a spatula (careful not to overmix).
Grease a baking pan with butter and sprinkle some semolina or flour. Pour the batter into the baking pan.
Add 8 thin slices of oranges on top of the batter.
Preheat the oven to 360°F (180°C), and bake the batter for about 45-50 minutes until golden.
Strain the syrup.
Pour the cold syrup over the cake as soon as it’s out of the oven.
Once covered in syrup, let the portakalopita absorb the syrup for at least an hour but preferably overnight! Then your portokalopita is ready to be enjoyed by you, loved ones, and your dinner guests.