Preheat your oven to 400°F. Wash and dry the potatoes, then pierce each one with a fork in six places. Rub generously with olive oil.
First Bake: Place potatoes directly on oven rack. Bake for 50-60 minutes, until a fork slides in with no resistance. Let cool for 10 minutes.
Halve and Scoop: Cut potatoes in half lengthwise. Scoop out the flesh into a bowl, leaving a 1/4-inch layer attached to the skin.
Make the Filling: To the potato flesh, add cream cheese, half the cheddar, chopped bacon, salt, pepper, and half the chives. Mash until combined. Taste and adjust salt.
Refill the Boats: Spoon filling back into the potato shells, mounding slightly above the edge. Top with remaining cheddar.
Second Bake (No Egg): Place filled potatoes on a rimmed baking sheet. Bake at 400°F for 15 minutes to set the filling and crisp the cheese.
Add the Egg: Remove from oven. Use the back of a spoon to carve a deep well in each filling. Crack one egg into each well. Season egg with salt and pepper. Return to oven and bake 10-12 minutes (white set, yolk jiggly).
Rest and Finish: Let potatoes rest 2 minutes. Transfer to plates. Top with remaining chives, flaky salt, and black pepper. Serve immediately.