Preheat the oven to 400 degrees. Spray a 10-inch angel food pan with cooking spray and coat with a light dusting of flour.

Bring the raisins and vin santo to a simmer in a very small saucepan over high heat. Turn off the heat and set aside for the raisins to absorb the wine.

Leaving the peels attached, lay the orange halves flat side down and cut into ¼-inch-thick slices. Chop the slices into ¼-inch-thick cubes.

Put the eggs, baking soda, baking powder, kosher salt, and ½ cup plus 2 tablespoons of the granulated sugar in the bowl of a standing mixer fitted with the whisk attachment and mix on medium-high speed until the mixture thickens, 3 to 4 minutes. Gradually add the olive oil by pouring it down the side of the bowl in a slow, steady stream.

Reduce the mixer speed to low. Add one-third of the flour and mix, then the raisins, then again until you use everything up, finishing with the flour.

Add the chopped oranges and use a rubber spatula to gently fold them into the batter. Scrape the batter into the prepared pan and scatter the pine nuts over the top. Sprinkle the cake with the remaining ¼ cup granulated sugar (I only used 2 tablespoons) and stick the tufts of rosemary into the batter, distributing them over the surface of the cake in an attractive way.

Bake for 10 mins. Lower temp to 325 and bake 30 - 35 more until cake is golden brown and a toothpick comes out clean.