Step 1: In a small bowl, combine the warmed milk (105-115°F or 40-46°C), granulated sugar, and instant yeast. Stir gently and let it sit for 5-10 minutes until foamy, indicating the yeast is active.
Step 2: In a large mixing bowl, whisk together 2 ½ cups of the all-purpose flour, salt, garlic powder, dried dill weed, and black pepper (if using).
Step 3: Add the dill pickle brine, finely chopped dill pickles, melted unsalted butter, and the egg to the yeast mixture. Stir until well combined.
Step 4: Pour the wet ingredients into the dry ingredients. Mix with a wooden spoon or a stand mixer with a dough hook until a shaggy dough forms. If mixing by hand, turn the dough out onto a lightly floured surface. Knead for 8-10 minutes, gradually adding up to ½ cup more flour if needed, until the dough is smooth and elastic. If using a stand mixer, knead on medium-low speed for 6-8 minutes.
Step 5: Lightly grease a large bowl with oil. Place the dough in the bowl, turning once to coat. Cover the bowl with plastic wrap or a clean kitchen towel and let it rise in a warm, draft-free place for 1 to 1 ½ hours, or until doubled in size.
Step 6: Gently punch down the risen dough to release the air. On a lightly floured surface, shape the dough into a loaf. Place the loaf into a lightly greased 9x5 inch loaf pan.
Step 7: Cover the loaf pan with plastic wrap or a towel and let it rise again in a warm place for another 30-45 minutes, or until it has nearly doubled and looks puffy.
Step 8: Preheat your oven to 375°F (190°C). Bake the dill pickle bread for 30-35 minutes, or until the crust is golden brown and the internal temperature reaches 200-210°F (93-99°C).
Step 9: Remove the bread from the oven and immediately turn it out onto a wire rack to cool completely before slicing and serving. This helps prevent a soggy bottom and ensures the texture is perfect.