"How can I offer free shipping when a certain dollar amount is reached?"

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Short Answer:

In other words, you would like to avoid charging shipping if the shopper orders a certain amount.  To do this, create a promotion.  Detailed, step-by-step instructions below.

Detailed Explanation

1. Create a new promotion (MARKETING > New Promo)
2. Give it a name (you should not enter a promo code if you want everyone to get this automatcally)
3. Set the Promo Behavior Information to the following:
1. The discount will be a:  Percentage
2. Next to it, "Enter the value,"  set this to 1.00  (this means 100% if you noticed our instructions)
3. "If a percentage, a percentage of what?"  Set this to "Shipping"
4. If you want to limit it to a certain shipping method, then that is up to you.
5. Set "The discount will only occur when (the condition)" to "Subtotal meets or exceeds a specified amount."
6. Set "If the condition involves a target amount please enter it here" to your dollar amount.  So if you wanted to give free shipping on all orders over $100, then you would just enter 100 here.

Of course you can customize this promotion to your liking, so for example, you could say, instead of $100, if they order any 5 products, then they get free shipping.