If there were a definitive ranking of comfort foods, shepherd’s pie might just be number one. Step one: make a batch of buttery mashed potatoes. Step two: cook up a mean vegetable-enriched beef filling. Step three: enjoy fire-side with a cozy blanket and a glass of red wine. Okay, that might be overkill, but the red wine should be doable. If you can’t find red new potatoes for the topping, substitute with another waxy potato like Yukon gold or fingerlings.
Cover potatoes with cold water in a large pot. Bring to a boil, reduce to a simmer and cook until tender when pierced with a fork, 20 to 25 minutes. Drain and return to pot. Add warm milk and butter; mash until creamy. Season with 1½ teaspoons of the salt and several grinds pepper.
Heat 1 tablespoon of the oil in a large skillet over medium-high. Add beef and cook undisturbed, until browned on bottom, about 4 minutes. Add ½ teaspoon of the salt. Continue cooking, breaking up pieces with a wooden spoon, until browned all over, about 5 minutes. Using a slotted spoon, transfer beef to a bowl. Wipe out skillet.
Using same skillet, heat 1 tablespoon of the oil over medium-high. Add mushrooms and ½ teaspoon salt; cook undisturbed until golden, about 3 minutes. Add thyme and continue to cook, stirring occasionally, until golden all over, about 2 minutes. Transfer to bowl with beef.
Using same skillet, heat remaining tablespoon oil over medium. Add onion, celery, and garlic; cook until golden, stirring occasionally, 5 to 6 minutes. Return meat and mushroom mixture to skillet and add tomato paste; cook, stirring constantly, about 1 minute. Add stock and remaining ½ teaspoon salt; simmer until slightly thickened, 7 to 8 minutes.
Stir in carrots, peas, and Worcestershire; cook until peas are crisp-tender, 3 to 4 minutes. Transfer mixture to a 9 x 13-inch (or 3-qt) baking dish. Spoon then gently spread mashed potatoes on top.
Set baking dish on a rimmed baking sheet. Bake until filling is bubbling and top is golden in spots, 18 to 22 minutes. Let stand 15 minutes before serving.
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