
Hungry for something a little different? These thumbprint cookies bring together gooey cheeses and a rich tomato bourbon jam. The shortbread is buttery, cheesy, and crumbly, and every bite is lifted with sweet-savory jam. It’s a head-turning nibble you’ll want to share with your favorite people.
The first time I made these was for a winter get-together, and they vanished before anything else. Now, friends always look forward to these little showstoppers when they come over.
Lively Ingredients
- Semolina flour: Makes these cookies hold up and gives a slight crunch
- Monterey jack cheese: Melts smoothly and adds a creamy feel
- Unsalted butter: Keeps everything rich and tender
- Bourbon: Gives the jam a caramelly, grown-up kick
- Chili flakes: Add a light, tingly heat to balance things out
- Fresh rosemary: Brings a piney, fresh note
- White cheddar cheese: Lends that sharp, cheesy flavor
- Cherry tomatoes: The star in the jam, giving it sweetness
- Jalapeño: Gives just a kiss of mild spice to every mouthful
Easy Instructions
- Fill the cookies:
- After you’ve made dough balls, press your thumb into each and fill generously with jam so every bite is flavorful.
- Shape your dough:
- Whisk semolina and flour, then gently blend into your soft butter mix, so you don’t end up with tough cookies. Knead with floured hands and chill the dough for 30 minutes to keep things firm and easy to handle.
- Add the egg:
- Once your butter and cheese mix is creamed, crack in and fully blend the egg—you don’t want streaks! This helps the dough stick together.
- Mix up the butter base:
- Beat your soft butter, salt, and sugar until light and whipped. Mix in your cheese blend really well until it’s fully mixed in.
- Make the cheesy mix:
- Pulse grated cheeses, chopped rosemary, and jalapeño in a food processor until everything is tiny and combined evenly. Deseed your jalapeño if you’re not after serious heat.

Semolina flour totally changed the game for me here. My first tries came out fine, but once I tossed in semolina, the cookies held up way better and had that perfect bit of crunch. They never got soggy from the jam, and that’s the key.
Bold Bourbon Tomato Jam
This jam is where the magic happens! Toss halved cherry tomatoes, some apple cider vinegar, and sugar in a heavy pot. Pop in onion, garlic, spices, salt, and let it all cook down until thick and glossy. Pour in bourbon at the end for that deep punch of flavor. You want the jam cooled down all the way before you spoon it into cookies, so making it the night before honestly saves you time.
Tasty Pairings
These cheesy cookies are a perfect snack with a charcuterie plate or cheese platter. They’re awesome with crisp bubbly like Cava or Prosecco—the acidity slices through the richness. Want to skip booze? Sparkling water with elderflower works great. I love serving them at the start of a dinner with a simple salad of bitter greens and zippy vinaigrette.
How To Store
Stash your dough in the fridge for up to three days if prepping ahead. Once baked, cookies are happiest in a sealed container at room temp—try to eat them within a day for the freshest taste, but they’ll be fine for two. Leftover jam is gold and will keep for two weeks in the fridge in a closed jar. Try it on everything!

Put these on your menu and you’ll have everyone talking—delicious, stylish, and totally memorable!
Frequently Asked Questions
- → Is it alright if I prep the bourbon tomato jam early?
Definitely! Go ahead and make the jam even a week before. Just toss it in a sealed jar in the fridge and give those flavors time to chill and get even tastier.
- → What if I can't find semolina flour?
No worries if you don't have semolina. Just swap with all-purpose flour instead. Your cookies will be a bit smoother and not as golden, but they'll still taste awesome.
- → How much kick do the jalapenos add?
They're just a tad spicy if you use one seeded jalapeno. Ditching the seeds keeps things mellow. Want more heat? Leave some seeds or add extra jalapenos.
- → Can bagged shredded cheese work for this?
Grating your own cheese is the way to go, since the pre-shredded kind can have weird stuff in it that messes with texture. If you must, check for any without extra powders or starch added.
- → What's the best way to store these cookies?
Keep them in a sealed container in the fridge for up to three days. Reheat in a 300°F oven for 5 to 10 minutes before serving and they're just right again.
- → Got a swap for the bourbon if I don't want booze?
You sure do! Use apple juice plus a dash of vanilla and a hint of liquid smoke. Or check for alcohol-free bourbon at specialty shops—works great too.