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Pre-heat the oven to 425F.
Using a fork, pierce steam holes evenly over each potato. Rub with a little olive oil and sprinkle with salt.
Place the potatoes directly onto a rack set in the centre of the oven. Bake for 50-60 minutes, depending on the size of your potatoes. Once a knife slides in right to the middle, they are baked through.
Remove and cool till you can handle them. Slice off the top section, exposed enough of the interior that you can get a spoon in to scoop it all out.
Scoop out the filling, but leave a wall of flesh around the exterior so that the potato will maintain its structure once filled with shepherd’s pie filling and placed in the oven to continue baking. I leave around 1/6 inch but no more than 1/4 inch of ‘wall’.
Place all the scooped out filling into a bowl. Add the butter, milk (start with less), salt, pepper (start with less of the salt and pepper), nutmeg and cheddar cheese. Blend with a fork till rustically smooth (it doesn’t have to be perfect, without lumps! If you need more milk to break up the potatoes, only add 1 tbsp at a time, you don’t want them to become too loose. You want just a little firmer than classic mashed potatoes. The size of your potatoes will determine how much milk and even cheese to add.
Taste and re-season as desired.