Automated Shipping Label Selection

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We offer free shipping on all orders and free expedited shipping on orders over $75.  Customers also have the option to pay for expedited shipping.  The problem is our employees don't always see if a customer qualifies or has paid for expedited shipping, so they pay and print out shipping labels for our default service. 

Is there an app that can help with this?  We need to foolproof our shipping label options so the correct option will always be automatically selected.