Reduce the heat and simmer over low heat for about 5 minutes. Take off the heat and cool completely.
Once cool place in a lidded container and stash in the fridge, ideally overnight and up to several days, until ready to use.
When ready to bake the cookies, drain any remaining liquid from the cranberries, pat dry and set aside.
Preheat your oven to 350F and line several baking sheets with parchment paper. In a medium bowl add the brown sugar and butter and beat with a spatula until light and fluffy; the mixture should no longer appear dense and the color should have lightened slightly. Add in the olive oil mixing until the oil is completely emulsified into the mixture. Add in the egg, vanilla paste or extract, baking powder, salt and baking soda and mix until no traces of egg are visible, and it has become one cohesive, delicious smelling mixture.
Gently fold in the flour stopping when there are still traces of flour visible. Add in the bourbon-soaked cranberries and chocolate and stir until evenly distributed throughout the dough being careful to use as few strokes as possible so as not to overmix the dough.
Scoop 2 tablespoons of dough onto the prepared baking sheets, leaving 3 inches between cookies to allow for spreading. Bake for 11 minutes in the center of the oven. As soon as they’re out of the oven, use the edge of a spatula to nudge the cookies back into a circle. Let cool on the baking sheet for 10 minutes to set and collapse a bit. Sprinkle with sea salt flakes, if using, while still warm.
TIP: For the prettiest cookies, roll the cookie dough into a ball and then place the side with the most chocolate and cranberries facing up.