In a medium saucepan, heat 1 tablespoon extra virgin olive oil over medium-low heat.
Add shallot and cook until softened and translucent, about 2 – 3 minutes.
Add garlic and cook 30 seconds until fragrant. Lower the heat if either begins to brown.
Add cranberries, orange peel, orange juice, water, brown sugar, balsamic vinegar, cinnamon, allspice, and salt.
Increase heat and bring to a simmer, stirring occasionally, until the cranberries burst and the mixture thickens, about 12 – 15 minutes.
Remove from heat. Discard orange peel.
Stir in the dried cranberries and a few grinds of black pepper.
Let the chutney cool slightly — it will thicken as it cools.
Finish with 2 tablespoon extra virgin olive oil. Serve at room temperature or chilled.