- In a large pot over medium-high heat, brown the beef on all sides in the oil. Season with salt and pepper. Transfer to a plate.
- In the same pot over medium heat, brown the onion and garlic. Deglaze with the wine. Add the broth and return the meat to the pot. Bring to a boil. Cover and cook over medium-low heat for about 2 hours. Remove the cover and cook for about 30 minutes or until the meat is fork tender and the sauce has reduced by half.
- With the rack in the middle position, preheat the oven to 350 °F (180 °C).
- Drain the meat and place on a work surface. Pour the cooking juices into a 11 x 8-inch (28 x 23 cm) baking dish. Shred the meat while removing most of the fat. Spread the meat into the baking dish and toss with the cooking juices. Set aside.
- Meanwhile, in large pot of salted boiling water, cook the potatoes for about 25 minutes or until tender. Drain. With a potato masher, crush the potatoes with the butter. Add the milk and garlic. Season with salt and pepper.
- Spread the mashed potatoes over the shredded meat. Bake for 30 minutes. Place the cheese slices on top of the pie. Finish cooking under the broiler for about 5 minutes or until the cheese is lightly browned. Let rest for 10 minutes.
- Meanwhile, in a skillet, cook the tomatoes in the oil with the maple syrup and harissa. Spread the stewed tomatoes over the hot sheperd’s pie. Sprinkle with the parsley. Serve immediately.