Taste the olives that you’re using to make sure they are not too salty. (Oil-packed olives are usually less salty.) If they are salty, or if they were packed in brine, rinse the olives well, or soak them in water for up to 4 hours to remove some of the salt.

Preheat the oven to 400 degrees then line a rimmed baking sheet with parchment paper. Cut bacon strips into thirds cross-wise to form 30 short strips.

Cut each olive and each tomato in half at its equator. Put the cut sides of an olive and a tomato together, wrap in a strip of bacon and secure with a toothpick. Arrange bacon wrapped olives and tomatoes on the baking sheet on their sides with the bacon seams facing up. Space as far apart as possible.

Bake for 20 minutes then remove from the oven. Turn each one over then sprinkle with a bit of the brown sugar. Return the olives to the oven to bake for an additional 10–15 minutes or until the bacon reaches desired crispness. Remove from oven then let cool for 5 minutes before serving. Enjoy!