Combine yeast, 2 cups flour and salt in a Bosch bread machine. Add the milk, water, and oil and beat for about 2 minutes. Mix in the olives and add the remaining flour ½ cup at a time. The dough should be sticky and soft and just clear the sides of the bowl.
Drizzle the sides of a bowl with oil and put the dough in it to rise for one hour or until double the bulk. Cover with plastic wrap.
Scrape the dough out onto a greased cookie sheet or divide it evenly among eight 6-inch round cake pans at least one-inch deep. Spread and gently pull the dough, flattening it to fill the entire baking sheet or pans. Smear the top surface with olive pesto. Let rest uncovered at room temperature for 15 minutes. Pre-heat oven to 400°F.
Place the pans in the oven on the lowest rack for 15 minutes. Reduce the oven temperature to 350°F and place bread on the top shelf. Cook for an additional ten minutes. Time may vary according to your oven. The bread should be golden and spring back when pressed. Let cool and cut into squares or desired shapes.
TipsThe dough will be somewhat sticky. There is no need to add more flour. Cover the bowl that it is going to rise in, well with olive oil, and also spray the top of the dough with olive oil so that the plastic wrap will be easier to remove.
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