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Preheat the oven to 425 degrees and line two sheet trays with non-stick foil.
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Divide the sweet potatoes between the two sheet pans and drizzle evenly with olive oil and season with salt and pepper. Toss to coat.
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Roast for about 30 mins or until tender and golden brown. Remove from the oven and cool to room temperature.
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While the potatoes are roasting fry the bacon until crisp in a non-stick skillet. Remove the bacon to a paper towel-lined plate to drain and pour out all but 1 Tbsp bacon grease.
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Heat the pan over medium heat and add the diced peppers. Cook until softened and golden brown, about 5 mins. Cool to room temperature.
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In a large bowl lightly toss together the sweet potatoes, peppers, pineapple and herbs. Add the dressing and toss and then crumble the bacon into the bowl and stir just until combined.
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Season with salt and pepper if desired and serve.
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Dressing: Combine everything but the olive oil in a small food processor (alternatively you can whisk by hand) and process until blended. Add the oil and process until combined.
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*Salad can be prepared up to 3 hrs ahead and left at room temperature. Store leftovers in the refrigerator.