Preparation Steps

• Make the jam first so it can cool: combine halved cherry tomatoes, sugar, vinegar, diced onion, minced garlic, crushed red pepper, ground cumin, and 1/2 tsp kosher salt in a medium saucepan.
• Bring the tomato mixture to a steady simmer over medium heat, stirring occasionally. As the tomatoes soften, mash them gently against the side of the pan with a wooden spoon to break them down.
• Maintain a simmer and cook until the mixture reduces and thickens to a jammy consistency, about 15–20 minutes (times may vary). Remove the pan from the heat, stir in the bourbon, then let the jam cool to room temperature before chilling; refrigerate at least 2 hours or overnight.
• While the jam cools, prepare the cookie dough: in a large bowl, beat the softened butter with the granulated sugar and 1/2 tsp kosher salt until smooth and slightly airy, about 1–2 minutes.
• Stir in the egg and the lemon zest until just combined. Fold in both shredded cheeses, chopped jalapeño, and chopped rosemary so they’re evenly distributed in the butter mixture.
• In a separate bowl whisk together the flour and semolina. Add the dry mix to the cheese-butter mixture in two additions, folding with a sturdy spatula until a soft, slightly sticky dough forms. If needed, finish bringing it together with lightly floured hands.
• Cover the dough and chill in the refrigerator for at least 30 minutes (or up to overnight). Chilling firms the butter and makes shaping easier.
• Preheat the oven to 350°F. Line baking sheets with parchment paper. Using a small cookie scoop or spoon, portion dough into 1 1/4-inch balls (about 28–32 g each) and arrange 2 inches apart on the prepared sheets.
• Make a well in each dough ball using the back of a small spoon or a slightly floured thumb to create a generous indentation that will hold the jam. Return the trays to the fridge for 10–15 minutes while the oven finishes preheating to keep the cookies from spreading too much.
• Remove trays from the refrigerator and spoon about 1 teaspoon of chilled bourbon tomato jam into each indentation. Bake one sheet at a time (or two, rotating halfway) for 18–22 minutes, until the cookie edges are lightly golden and the bottoms are set.
• Let the cookies cool on the baking sheet for 5 minutes so the jam sets, then transfer to a wire rack to finish cooling. Do not stack cookies while warm—the jam will stick.
• Serve slightly warm or at room temperature. Cookies keep in a single layer in the fridge for up to 5 days; bring to room temperature before serving for best texture.