CARAMEL

• Pour your sugar into an even layer along the bottom of a medium-sized pot and place it over medium-low heat on the stove
• Stir every 20-30 seconds with a spoon - it will look like nothing is happening at first. As the sugar slowly melts, it will get a little clumped, and you’ll notice the color slowly change. Once the sugar is completely melted, immediately remove it from the heat
• Add your butter to your pot and whisk in
• Carefully stream your room temperature heavy cream into your pot and stir before mixing in your sea salt
• Set aside to cool at room temperature before assembly - can be lightly warm, but no hotter, or it will melt the frosting

CAKE

• Preheat oven to 350°F and grease and line a 9-inch round pan with parchment paper
• In a mixing bowl, whisk together your flour, baking powder, baking soda, and salt, and set aside
• In a separate large bowl, add your dark brown sugar and orange zest. Rub the zest into the sugar with your fingers to release the oils, until fragrant (about a minute)
• Crack in your eggs and whisk for 1 minute until the mixture pales in color. Pour in your olive oil, orange juice, buttermilk, and vanilla, and whisk until smooth
• Sift in your dry ingredients, mixing until just combined
• Pour your cake batter into your greased and lined pan
• Bake for 25 minutes, or until a toothpick inserted comes out clean with a few moist crumbs
• While your cake is baking, prep your simple syrup. In a small pot, combine your orange juice and sugar. Whisk over medium heat until the sugar dissolves, then reduce the heat and simmer for 2 minutes, or until lightly reduced. You’re not looking for thick syrup, but just lightly thickened to evaporate some water. Remove the pot from the heat, pour into a bowl, and allow the mixture to cool slightly
• Remove your cake from the oven and allow it to cool in the pan for 10 minutes. Invert onto a wire rack, and while still warm, use a pastry brush to brush all of the syrup on the cake (top and sides!)
• Cool completely before assembling

FROSTING

• Add your room temperature cream cheese and butter to a mixing bowl and beat for a minute until smooth
• Sift in your powdered sugar and carefully beat until all incorporated
• Mix in the vanilla and milk

ASSEMBLY

• Place all of your cream cheese frosting on top of the cooled olive oil cake and smooth out
• Drizzle over some of your caramel and then swirl it in with a spoon or spatula. Save the rest for drizzling over individual slices
• Top with fresh orange segments and, if desired, dehydrated oranges