In a large pot on the stove, boil cauliflower for 12-15 minutes until soft. Drain.
In a blender, add the vegetable stock, Italian herb seasoning, White Wine Vinegar, drained cauliflower and pumpkin puree. Blend until smooth.
Add the roasted garlic cloves by squeezing from the bottom of the clove so the garlic goes into the blender. Blend again.
Pour everything into a pot on the stove and simmer over low heat for about 30 minutes; stirring frequently. Add more vegetable stock if the soup becomes too thick.
Serve with crackers, crusty bread a salad and a pinch of Italian seasonings on top.