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Combine 1/4 cup prunes, Gorgonzola, breadcrumbs and 1/2 teaspoon thyme in a small bowl. Cut a horizontal slit along the thin edge of each chicken breast, nearly through to the opposite side. Stuff each breast with about 2 1/2 tablespoons filling. Use a couple of toothpicks to seal the opening. Season with salt and pepper.
Heat 1 tablespoon oil in a large nonstick skillet over medium-high heat. Add the chicken and cook until golden, about 4 minutes per side. Transfer to a plate.
Add the remaining 1 teaspoon oil, shallot and the remaining 1/2 teaspoon thyme to the pan; cook, stirring, until fragrant, about 1 minute. Add wine and the remaining 1/4 cup prunes. Reduce heat to medium; cook, scraping up any browned bits, until most of the wine evaporates, about 2 minutes. Whisk broth and flour in a small bowl until smooth; add to the pan and cook, stirring, until thickened, about 2 minutes.
Reduce heat to low, return the chicken and any juices to the pan and turn to coat with sauce. Cover and cook until the chicken is cooked through, 3 to 5 minutes more. Remove toothpicks, slice the chicken and top with the sauce.