Combine 1 1/2 cups water, sugar, and yeast in the bowl of a stand mixer, stirring with a whisk; let stand 10 minutes. Stir in 2 tablespoons oil.
Weigh or lightly spoon flour into dry measuring cups; level with a knife. Combine flour, rosemary, and salt. Add flour mixture to yeast mixture. Mix on low speed with dough hook just until dough comes together; mix on medium speed 6 minutes. Scrape dough into a large bowl coated with cooking spray (dough will be soft and sticky); coat top of dough with cooking spray. Cover and let rise in a warm place (85°F), free from drafts, 1 1/2 hours or until doubled in size.
Punch dough down. Spoon dough onto a parchment paper–lined jelly-roll pan. Pat dough out into a 14 x 10–inch rectangle by dimpling dough with fingertips. Cover and let rise 1 hour. (Tip: Another jelly-roll pan, upside down, makes a great cover.)
Preheat oven to 425°F.
Uncover dough. Drizzle with 1 1/2 tablespoons oil. Scatter grapes and olives over dough, barely pressing into dough. Sprinkle with pepper. Bake at 425°F for 30 minutes or until lightly browned on bottom. Cool on a wire rack.
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