Heat a large Dutch oven over medium-high heat. Add 1½ teaspoons olive oil.
Sauté onion, thyme, and garlic for 5 minutes, until softened.
Add potatoes, chicken stock, ½ teaspoon salt, and bay leaf.
Bring to a boil, cover, reduce heat, and simmer 35 minutes or until potatoes are very tender. Remove bay leaf.
While soup simmers, preheat oven to 400°F.
Toss cauliflower with remaining olive oil, ¼ teaspoon salt, and ¼ teaspoon pepper.
Roast 30 minutes, turning once, until golden and tender.
Transfer roasted cauliflower to a blender. Add milk and blend until very smooth.
Add half the potato mixture to the blender and pulse 5–6 times until chunky-smooth.
Repeat with remaining potatoes.
Return soup to pot over medium heat. Stir in remaining pepper, ½ cup green onions, and sour cream until creamy and heated through.
Serve hot with cheddar cheese, bacon, and remaining green onions.