Prep Time 20 minutes mins
Cook Time 35 minutes mins
Resting Time 5 minutes mins
Total Time 1 hour hr
Choose a steak with good marbling for the best flavor and tenderness, and always pat it dry before searing to promote a deep crust. If your skillet smokes heavily, reduce heat slightly but keep it hot enough to maintain sizzle. For extra-smooth mash, pass the roasted squash through a potato ricer or blend briefly with an immersion blender, adding a splash more warm milk if needed. Maple syrup balances squash sweetness—reduce or omit if you prefer savory, or swap for a teaspoon of brown sugar. Warm plates help the mash stay velvety and the steak juicy; pop them in a low oven for a few minutes before serving.