Place the potatoes in a large pot and fill it with cold water. Bring the water to a boil. Simmer the potatoes until they are just barely fork tender. Strain the potatoes and let them cool slightly.
Preheat the oven to 450 degrees F.
Brush a baking sheet with 1 1/2 tablespoons of olive oil. Place the potatoes on the sheet. Use your hand or the bottom of a glass to smash them once, trying to keep them in one piece. It’s okay if they kind of break apart!
Drizzle or brush the remaining olive oil over the potatoes. I actually use an olive oil spritzer for this part! Sprinkle the potatoes with the chipotle chili powder, salt, pepper and garlic powder.
Place the sheet in the oven and roast the potatoes for 20 minutes, until golden and crispy. While the potatoes are cooking, heat a skillet over medium-low heat and cook the bacon until crispy.
Remove the potatoes from the oven and sprinkle cheddar on the tops of each. Bake for 5 minutes more, until the cheese melts. Remove and top with yogurt/sour cream, bacon and chives. Serve immediately!