Slice the garlic head in half. Drizzle the exposed cloves with olive oil and season with salt and pepper. Wrap in foil and roast on a baking sheet at 400ºF (204ºC) for 40 minutes. Let cool, remove cloves from their skins and set aside.

Add the yeast to the water and let sit for 10-15 minutes until the yeast starts to foam. While the yeast is activating, stir together flour, salt, and oregano in a large mixing bowl. Add yeast mixture and all remaining ingredients to the bowl and mix together just until combined. The dough should look a little sticky and stringy and there should still be a little flour around the edges of the bowl. Cover and let rise somewhere warm until it has doubled in size.

When you're ready to bake your bread, preheat oven to 450ºF (232ºC) with a Dutch oven or covered baking dish inside the oven. At this point your dough should be puffy and have risen to almost level (or higher) with the top of the bowl. It will be sticky and well-hydrated.

While the oven is preheating, flour your hands (or a dough scraper, if using) as well as your shaping surface. Pull the dough away from the edges of the bowl and turn it onto the floured surface. Adding bits of flour if needed to prevent sticking, gently fold the dough into itself several times just until a soft, flour-covered ball is formed. Transfer dough to parchment paper and let sit until the oven is pre-heated (~20 minutes).

Once the oven is preheated, score your loaf then remove the Dutch oven from the oven. Next, transfer the dough, still on the parchment, into the Dutch oven. Cover and bake for 30 minutes, then remove the cover and bake for 15-20 minutes more. Your bread will be done once the top is browned. Using parchment edges, lift bread from Dutch oven and transfer it to a wire cooling rack to let cool for up to an hour before slicing.