Preheat a large, heavy-bottomed pot over high heat with two tablespoons of EVOO, about two turns of the pan.
Place the pieces of tenderloin onto a sheet tray and season them with salt and freshly ground black pepper. Toss with flour until well-coated.
Once ripples appear in the oil and it starts to very lightly smoke, add the pork to the pot and sear it until well-browned on all sides, 7-8 minutes (lots of brown bits will remain on the bottom of the pot). Remove the meat to a platter and reserve.
Add the remaining two tablespoons of EVOO to the pot along with the onion, carrot, celery, bay leaf and thyme, and season with salt and freshly ground black pepper. Cook the vegetables until they begin to tenderize, about 6-8 minutes then add in the apples, allspice and cranberries, and cook until the vegetables are quite tender, 3-5 minutes.
Deglaze the pan with the cider, scraping up the brown bits that are stuck to the bottom of the pot with a wooden spoon. Add in the chicken stock and toss the pork back into the hot tub. Bring the mixture to a boil then reduce the heat and simmer for 8-10 minutes or until slightly thickened. Pull out the bay leaf and thyme sprigs from the pot and discard them.
To serve, line the bottom of six bowls with chunks of bread. Ladle the stew on top of the bread and enjoy!