Drain the mozzarella pearls and set them on a paper towel to blot off extra moisture. Halve the grape tomatoes and set them cut-side down on a paper towel as well so they are not dripping when you thread them. Fold each pepperoni slice in half so it is easier to slide onto the skewer without tearing.

Pick up one short cocktail skewer and thread a folded pepperoni slice onto it first, pushing it down toward the flat end so it sits at the bottom. Follow with a mozzarella pearl, then a halved tomato placed cut-side facing the cheese. Repeat with another piece of pepperoni and a second mozzarella pearl if your skewer is long enough for two rounds. Aim for at least three pieces per skewer so each one feels substantial.

Repeat the threading process with the remaining skewers until all the ingredients are used up. You should get roughly 12 to 16 skewers depending on how generously you load each one and how large your ingredients are.

Arrange the finished skewers on a serving plate or lay them in a single layer inside a lunchbox container. In a small bowl, stir together the olive oil, Italian seasoning, garlic powder, salt, and pepper until combined.

Drizzle the seasoned olive oil evenly over the skewers, using a spoon to make sure each one gets coated. If you are packing these for lunch, drizzle the oil in the container so it pools at the bottom and the skewers soak it up without getting the lunchbox lid greasy.

Serve immediately for the freshest texture, or cover and refrigerate for up to 24 hours. If you are serving at a party or after-school gathering, set them out on a platter and let kids grab their own. They are ready at room temperature right from the fridge, no reheating needed.