Preheat oven to 400°F.

Cook bacon on a rimmed baking sheet until crisp, approximately 20 minutes.

Drain bacon on paper towels.

When bacon has cooled, crumble two of the strips into small pieces. (Should be about 1/4 cup)

Cut other two strips of bacon into 1-inch sections.

If a cherry tomato can’t sit flat on its bottom, cut the tiniest slice off of the bottom, so the tomato can sit flat in order to be filled.

Cut the tops off of the cherry tomatoes.

Using a small spoon, such as a 1/2 teaspoon, scrape out the insides of the tomatoes.*

Place the tomatoes upside down on a paper towel for 10 minutes.

Combine cream cheese and mayonnaise in a small bowl.

Season mixture with black pepper, add 1/4 cup crumbled bacon, and stir well.

When tomatoes have drained, place 2 arugula leaves in the bottom of each tomato.

Fill tomato cup with a hearty teaspoon of cream cheese mixture.

Garnish each with one of the bacon sections.