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Step 1
In a stand mixer with the dough hook, mix the flour, yeast and sugar on medium until combined, about 30 seconds. With the mixer on low, drizzle in the water, then increase to medium and mix to form a wet, smooth dough, about 5 minutes. Turn off the mixer, cover the bowl and let stand for 10 minutes. Meanwhile, coat the bottom and sides of a large bowl with 2 tablespoons oil; set aside.
Step 2
Sprinkle the table salt over the dough, then knead on medium until smooth and elastic, about 5 minutes; the dough will be wet and clinging to the sides of the bowl. Using a silicone spatula, scrape the dough into the oiled bowl. Dip your fingers into the oil pooled at the sides of the bowl and dab the surface of the dough until completely coated with oil. Cover with plastic wrap or a plate and let stand at room temperature for 5½ to 6 hours; during this time, the dough will double in volume, deflate, then rise again (but will not double in volume again).
Step 3
After the dough has risen for about 4½ hours, heat the oven to 500°F with a baking steel or stone on the middle rack. Brush the cups of a standard 12-cup muffin pan with 2 tablespoons of the remaining oil.
Step 4
When the dough is ready, use a spring-loaded ice cream scoop or 2 spoons to divide it evenly among the prepared muffin cups; each cup should be about two-thirds full. If needed, use kitchen scissors to cut the dough for easier portioning. Let rest, uncovered, in a warm, draft-free spot for 10 minutes. Meanwhile, place the tomatoes in a medium bowl and use a potato masher to lightly crush them.
Step 5
Divide the olives and tomatoes among the muffin cups, firmly pressing them into the dough. Let rise, uncovered, in a warm, draft-free spot for 20 minutes.
Step 6
Drizzle the focaccia with the remaining 4 tablespoons oil, evenly dividing the oil. Sprinkle with the oregano, followed by flaky salt and pepper. Place the muffin pan on the baking steel and bake until golden brown and beginning to pull away from the sides of the muffin cups, 14 to 18 minutes.
Step 7
Cool in the pan on a wire rack for about 5 minutes. Using a small spatula or fork, lift out each bread and set it directly on the rack. Serve warm or at room temperature.