Pat your chicken breasts dry using paper towels, and then liberally season each side with salt & pepper.
In a large heavy bottomed skillet, such as cast iron or a Dutch oven, heat 1 tablespoon of olive oil over medium high heat.
Stir in the minced shallot, and cook just until softened and beginning to caramelize- about 1-2 minutes.
Add the cranberries, orange juice, vinegar, and honey to the skillet- whisking until evenly combined.
Let the mixture simmer, cooking until the berries begin to burst and soften, about 5 minutes. Make sure to whisk the sauce frequently to ensure even cooking.
Once they've softened, use the whisk to lightly mash them. Don't pulverize them, just encourage them to burst. Now whisk in the ginger, all spice, salt, and pepper until combined. Don't be alarmed if the mixture's thick. That's ok!
Using a spatula, carefully scrape the cranberry orange sauce into a waiting mixing bowl. Try to get every last bit out of the skillet. Cover the bowl with foil so that the sauce stays warm, and set aside.
Using a folded up paper towel, wipe the skillet clean being careful not to burn your fingers as you do.
Add the remaining olive oil, and heat it over medium high heat.
Once it's heated through, add the chicken breasts to the skillet. Let the chicken cook, undisturbed for 5-7 minutes, until nicely golden brown. Once seared, flip them, and sear the other sides, roughly 4-6 minutes or until the juices run clear.
Flip the chicken breasts over carefully, so as not to break up or tear apart, and then spoon the cranberry sauce evenly over top.
Remove the skillet from heat, and cover with a lid or aluminum foil, and let everything rest for 5 minutes.
Serve the chicken with fresh herbs for garnish, and extra cranberry orange sauce on the side for dipping.