In a medium bowl, whisk together the flour, sugar, salt and paprika.
Using a pastry cutter or food processor, cut in the butter into the dry ingredients until small crumbles form.
Add the chopped jalapeños, sharp cheddar cheese, and milk to the bowl; mixing until evenly mixed.
Turn the dough out onto a well-floured surface and roll dough to about 1/8” thickness. Using a knife, pastry or pizza cutter slice the dough into 2”x 2” squares.
With your dough cutter or spatula, transfer the crackers onto baking sheets lined with a Silpat silicone sheet or parchment paper. Pierce the top of each cracker with a small fork.
Lightly brush tops of crackers with olive oil and sprinkle with a smoked sea salt, or regular if you don't have it.
Bake at 375°F for 24-26 minutes, or until crackers are golden brown. Allow crackers to cool on a rack before serving. Will keep 5 days in an airtight container.