Arrange the steak strips on a cutting board and season lightly with salt and pepper. Use a sharp knife to trim any excess fat or uneven edges for uniform wrapping.
Wrap each steak strip with a half strip of bacon, securing it in place with a toothpick or small skewer. Ensure the bacon overlaps slightly to hold during cooking.
Heat the skillet over medium-high heat and add vegetable oil. Once hot and shimmering, carefully place the bacon-wrapped steak bites into the pan, spacing them evenly.
Sear the bites for about 3-4 minutes per side, using tongs to rotate and ensure even browning. Look for a golden-brown color and crispy bacon edges as visual cues of crispiness.
Once evenly cooked and crispy, remove the bites from the skillet and let them rest for 2 minutes. Remove the toothpicks carefully, revealing juicy steak and crispy bacon.
Serve immediately, with the bacon crispy and the steak hot and tender, showcasing a contrasting texture and smoky aroma.