Preheat oven to 425°F.
Toss the cauliflower florets with 1 tablespoon of olive oil, then spread them onto a sheet pan and season with salt and pepper.
Roast, tossing halfway, for 20-25 minutes or until just fork-tender.
While the cauliflower is roasting, heat the remaining olive oil in a Dutch oven or stock pot over medium heat.
Add the bacon and cook, stirring frequently, until it's just starting to crisp.
Mix in the onion and garlic and cook an additional 2-3 minutes or until softened.
Stir in the creamed corn, evaporated milk, and vegetable stock.
When the cauliflower is done roasting, stir it into the soup.
Taste and season with salt and pepper, as needed.