Pour 24 grams (roughly 2 tbsp) olive oil into a 9" by 13" pan. Tilt the pan side to side and front to back ensuring the oil covers the entire bottom of the pan.
Add the flour, active dry yeast, fine sea salt, warm water and 36 grams of olive oil to the bowl of a stand mixer and, using the paddle attachment, beat on high for approximately 60 seconds. The dough will be very wet.
Using a rubber spatula scrap the dough into the prepared pan. Cover and let it rise at room temperature for approximately 1 hour. Once risen the dough should fill the pan in it's entirety.
Preheat the oven to 375°F.
While the oven preheats and the dough is rising cut out the pepper pumpkins. The easiest way to do this is to cut a pepper from top to bottom along one side of the pepper. Then, using your fingers, gently pull the pepper open trying to keep it as much intact as possible only letting the pepper tear where needed in order to create a flat surface. Once this has been done cut out pumpkins using the pumpkin cookie cutter.
Once the dough has fully proofed drizzle it lightly with the remaining 6 grams of olive oil. Sprinkle with crushed garlic and oregano. Then using lightly oiled fingers create holes by gently pressing down on the dough. You should press down firmly enough that your fingers touch the bottom of the pan, but not so firm that you tear the dough.
Place in the oven and until golden brown, approximately 25 to 30 minutes.
Remove bread from the oven and allow to cool in the plan for 5 minutes before turning it out onto a cooling rack and allowing it to cool more completely. Serve warm or at room temperature.