Take the rind off the brie, then slice it into thin, even pieces. Cut your turkey so it fits the bread without hanging over the edges. Open the cranberry sauce and slice it into four neat rounds.
Lay out two slices of thick sourdough on your cutting board. Spread the brie over each slice as evenly as you can. I press it down gently so it reaches the corners and every bite gets cheese.ti
Stack two slices of turkey on each brie-covered slice. Add two cranberry slices, then top with one slice of havarti. Close each sandwich with the remaining bread slices.
Brush the top slice of each sandwich with olive oil. A thin, even coat gives you that deep golden crust. Skip the heavy pour, because too much oil makes the bread greasy.
Place the sandwiches oil-side down on a hot grill. Brush oil on the new top slice, close the lid, and cook for 3 to 4 minutes. Watch closely, because the bread can burn fast.
Carefully flip each sandwich and cook for another 1 to 2 minutes. You want the bread crisp and the cheese fully melted. Take them off the heat as soon as they look golden.
Let the sandwiches cool for a few minutes so the cheese sets a little. Then cut each one in half with a sharp knife. Serve right away while the center is still melty.
No grill? Heat a lightly greased skillet over medium-low heat and butter the outside of each slice. Cook 3 to 4 minutes on the first side, flip once, and cook 2 to 3 minutes more. I like this version when I want a buttery, diner-style crust.