I added a custom shipping module which charges 9.95 per order up to $49.99. I selected US and all states. I selected to activate the module. It's the only shipping module activated.
 
I logged in with my registered account and added one item to my cart which costs $4.99 then went to the checkout. It's not adding any shipping to the order.
 
Am I missing a step?

You have shipping module, but shipping methods are selected right? Also, do you have a weight requirement? Is the weight set from 1-x on shipping?
 
Just a couple suggestions

Thanks for the reply! You are right, the weight requirement was wrong. I had a weight in there as a test, but my shopping cart exceeded the weight and it didn't click for me that it would knock it out.
 
Thanks :)