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Generally speaking when a recipe calls for a cup of a fresh herb like cilantro, how tight to I have to cram it into the measuring cup?

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Oh man. That's a lot of cilantro. Some people are more sensitive than others, but make sure you like it a lot before putting that much in a dish.

In a perfect world we would all have ready access to scales and all recipes would list ingredients like these by weight instead of volume. That said, reality tends to lean more in favor of the volume-based approach.

How much you pack an ingredient varies by ingredient-to-ingredient. Brown sugar is a great example of an ingredient that is traditionally packed firmly into the measuring cup.

For an herb I would say "almost none" is the right amount of packing. Recipes will usually call for a minced or chopped volume. The herbs should settle down into the measuring cup fairly well. Fill it to be level with the brim like you would with other ingredients. Also, be sure to check if the recipe calls for "1 cup chopped cilantro" or "1 cup cilantro, chopped" as those could indicate if the measurement is to be made before or after chopping.

The best part about herbs is that it's completely subjective. Cook to your preference and make a note for next time. Adjust over time to find the right answer for you. As Aronut says in this answer, "Volume measurements of herbs are hopelessly imprecise to begin with... The most reliable way to know if you've got the right amount is to simply taste it."

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    It's for schug which is a dip made of basically cilantro garlic and jalapeño peppers. I just felt like I could have gone through the whole bunch stuffing into the measuring cup – y.lub Feb 16 '15 at 16:21
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    Most herb measurements are more like 1 tablespoon of chopped cilantro, and I've only ever lightly packed the herb into a tablespoon measure -- I think you're spot on with the "almost none" advice. – Erica Feb 16 '15 at 17:47
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    The recipe calls for the "cup" of cilantro, 5 jalapeños (I also threw in a habanero), 2-4 cloves of garlic, olive oil, cumin and salt to taste (and I put in a splash of lemon juice). I personally like the taste of cilantro but I find the smell of the bunches overwhelming when I wash it. – y.lub Feb 16 '15 at 19:16
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    My wife and I both love cilantro/coriander (it took me a while to appreciate it however) however a couple of my siblings are quite sensitive to it so I'm forced to tone it down when I cook at my parents. I made a really good dopiaza once which everyone enjoyed - except for my sister. She was put off after a bite because she could taste the coriander. -_- – NRaf Feb 16 '15 at 20:24
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    "In a perfect world we would all have ready access to scales and all recipes would list ingredients like these by weight instead of volume." Your perfect world would be Europe, then. Solids are almost always measured by weight in European recipes, unless the quantity is less than a tablespoon or so. And, unless you're baking, you probably don't need scales: for example, you can eyeball 200g of rice by just using a fifth of a one-kilo bag. – David Richerby Feb 17 '15 at 0:29
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Depends on how finely sliced it should be for the dish 😁.

When sliced (or not), sprinkle in a cup, without compressing, when full, done!

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It's just a guideline. A dip like that is to taste, but a cup of cilantro is a great place to start. You decide how much the cup should hold :)

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