Hi, @dmburkey !
I'd be happy to take a look into this with you. The first thing we'll want to do is take a look into why the refund may be failing. Open the order that you've attempted to process the refund for and scroll down to the order timeline. You should see some error messaging which will elaborate on the issue. Please feel free to relay that to me here and we can continue troubleshooting together.
This could be occurring for a number of reasons so having that error messaging will be helpful. My assumption is that your Shopify Payments account may have a negative balance. If this is the case, refunds are listed as Pending until you have made enough sales to have a positive balance in your Shopify Payments account, and then you can successfully issue a refund.
Just to be clear, I've also added the steps to ensure we're going through the proper process:
From your Shopify admin, go to Orders.
Click the order that you want to refund.
Enter the shipping amount that you want to refund into the Shipping field.
Hope to hear from you soon!