I have never used CoolCart, but it appears to be similar to many other third party shopping carts. I suggest looking at the user support for discounted items or simply contact the technical support for the cart.
If they have no way of doing it, you can put a message on the cart and site to have the customer simply add the free item, if their subtotal is $50 or more. You then set up a link to the free item and in its shopping cart code make the price zero and add a 6.99 value to shipping for it. If someone adds the item without spending the required minimum, you would need to credit the 6.99 back and not send the item.
Of course, this will depend how you have shipping already set up with the cart.
Another thought is the coupon option the cart features. Explore that.
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DrTandem's San Diego Web Page Design, drtandem.com
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