. Prepare the Filling:
Preheat oven to 375°F (190°C).
In a large skillet over medium-high heat, add olive oil.
Add shallots, garlic, and mushrooms, cooking for 5-6 minutes until the mushrooms soften.
Add 2-3 tbsp water if needed to help the mushrooms cook down.
Stir in chopped spinach and cook for 1 more minute until wilted.
Remove from heat and let cool slightly.
Prepare the Flank Steak:
Butterfly the flank steak by slicing it lengthwise without cutting all the way through. Open it flat.
Gently pound the steak using a meat mallet to even thickness (avoid making holes).
Season both sides with salt and black pepper, then flip it over.
Assemble the Pinwheels:
Lay provolone cheese slices evenly over the steak.
Spread the cooled spinach-mushroom mixture over the cheese.
Tightly roll up the steak from one end, making a log shape.
Use kitchen twine to secure the roll at 1-2" intervals.
Slice the rolled steak into individual pinwheels (about 1 ½" thick each).
Cook the Pinwheels:
Heat a large oven-safe skillet over medium-high heat for 2-3 minutes.
Add 1 tbsp butter and place the steak pinwheels in the skillet.
Sear for 2-3 minutes, then flip.
Add the remaining 1 tbsp butter and the fresh oregano & thyme. Cook for another 2-3 minutes.
Bake to Finish:
Transfer the skillet to the preheated oven.
Bake for 5-10 minutes, depending on desired doneness:
5 minutes = medium-rare
8 minutes = medium
10 minutes = medium-well
Remove from oven and let rest for 5 minutes.
Serve & Enjoy:
Remove kitchen twine and serve warm.
Garnish with freshly grated Parmesan.
Pair with roasted vegetables, mashed potatoes, or a fresh salad.