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Bring all ingredients except jalapeños to a boil in a medium sized pot (4-5 cloves smashed garlic, 2 cups white vinegar, 2 cups water, 1/2 cup sugar, 2 tablespoons kosher salt, 2 teaspoons dried oregano).
Add jalapeño slices to the pot, stir together, and remove from heat. Let sit for at least 10 minutes.
Use tongs or a slotted spoon to transfer the jalapeños to a jar. Once all the peppers are in there (you can smush them in quite a bit to make them fit), pour enough brine from the pot in the jar to fill it up. Discard any remaining brine.
Allow the pickled jalapeños to cool in your refrigerator for about an hour before consuming. Store in your fridge for up to 2 months for optimal freshness.