Activate the Yeast: In a small bowl, combine the sugar and yeast. Pour the warm water over this mixture and stir gently. Let it sit for 5 to 10 minutes, or until it becomes frothy and bubbly, signaling the yeast is active.
Prepare the Dough Base: In a large mixing bowl or the bowl of a stand mixer fitted with a dough hook, whisk together the flour and salt. Make a well in the center and pour in the yeast mixture along with the olive oil. Mix on low speed or stir with a wooden spoon just until a rough dough starts to form.
Knead the Dough: Transfer the dough to a floured surface. Knead by hand for about 10 to 15 minutes, gradually adding more flour as needed (about 1 tablespoon at a time) until the dough is smooth, elastic, and only slightly sticky. Alternatively, use the stand mixer on medium speed with the dough hook for 5 to 7 minutes, adding flour gradually until the same texture is achieved.
First Rise: Lightly grease a large bowl and place the dough inside, turning it to coat with oil. Cover the bowl with plastic wrap or a damp towel, and leave it in a warm spot for about 1 hour, or until the dough has doubled in size.
Prepare Herb Butter Mixture: While the dough is rising, combine the softened butter, chopped parsley, minced garlic, and a pinch of salt in a small bowl. Stir well until all ingredients are evenly mixed.
Shape the Dough Logs: Once risen, gently punch down the dough to release air. Divide it into two equal portions. On a lightly floured surface, roll one portion into a rough rectangle about 14 by 8 inches. Spread half of the herb butter mixture evenly across the dough surface. Sprinkle ½ cup shredded cheddar and 2 tablespoons Parmesan cheese evenly over the buttered dough. Add a light sprinkle of black pepper. Roll the dough tightly along the longer side into a log and pinch the seam to seal.
Slice and Arrange in Pans: Place the log seam-side down on the floured surface. Using a sharp serrated knife, cut the log into 1-inch slices, slicing almost through but keeping the base connected so the rolls stay together. Carefully transfer the log into one of the prepared 8-inch round pans, forming a ring shape with the cut rolls facing up. Repeat with the second dough portion to create a second ring in the other pan.
Final Rise and Bake: Spread or dollop the remaining herb butter mixture over the top of the rolls in both pans. Cover loosely with a clean kitchen towel and let rest for 15 to 20 minutes to rise again. Meanwhile, preheat the oven to 400°F (200°C). Bake the bread rings for 20 to 25 minutes, or until the tops turn a deep golden brown and the bread sounds hollow when tapped.
Cool and Serve: Remove the pans from the oven and allow the bread to cool slightly before serving. Pull apart the rolls to enjoy warm, gooey cheesy goodness with every bite.