Maple Bourbon Glazed Steak & Asparagus

INGREDIENTS

For the steak:

• 1 1/2 pounds sirloin steak tips, flap meat, or flank steak, cut into 3-inch pieces
• 1/4 cup tamari or soy sauce
• 2 tablespoons vegetable oil
• 2 tablespoons bourbon
• 2 tablespoons maple syrup
• 2 cloves garlic, minced
• 1 teaspoon Dijon mustard
• 1/4 teaspoon freshly ground black pepper

For the asparagus:

• 2 tablespoons vegetable oil
• 1 pound asparagus, trimmed
• 1/3 cup low-sodium chicken broth
• 1 tablespoon apple cider vinegar
• 1/8 to 1/4 teaspoon red pepper flakes
• 2 tablespoons unsalted butter

1. Marinate the steak: Place the steak in a single layer in a 9x13-inch baking dish or in a resealable gallon plastic bag; set aside. Whisk the remaining ingredients together in a small bowl. Pour over the steak and flip the steak to coat. Cover the baking dish or seal the bag, and refrigerate at least 1 hour or up to 4 hours.

2. Cook the steak and asparagus: Heat 2 tablespoons vegetable oil in a large frying pan or cast iron skillet over medium-high heat until shimmering. While the oil is heating, remove the steak from the marinade and pat dry with paper towels. Add the steak pieces to the pan (it's okay to crowd the pan as long as they're in a single layer) and sear until browned and the thickest piece registers 120°F to 125°F for medium-rare steak, 3 to 4 minutes on each side. (Or cook to 130°F to 135°F for medium steak, and 140°F to 145°F for medium-well steak — add a minute or two for every 10 degrees needed.) Transfer to a serving platter or clean cutting board and set aside in a warm place or cover loosely with aluminum foil.

3. Reduce the heat to medium. Add the asparagus, broth, vinegar, and amount of desired red pepper flakes and cook, stirring occasionally, until the asparagus is crisp tender, 2 to 3 minutes. Remove from the heat, add the butter, and stir until melted and the sauce in the pan is glossy. Taste and season with salt and pepper as needed. Serve the sauce and asparagus with the steak, sliced if desired.

RECIPE NOTES

Storage: Leftovers can be stored in an airtight container in the refrigerator for up to 3 days.

Marinade: The marinade can be made and stored in an airtight container in the refrigerator for up to 2 days. Re-whisk before using.

Photo credit and more recipes from our friends at the kitchn