Invoice - Status Reason will not update

I am using CRM to create quotes, which turn to orders, which then get billed to customers. The status changes help me keep track of invoicing in QuickBooks. (since I can find no reasonable connector into QuickBooks)

Lately I have been unable to change the status to "Billed". When I select the "Create Invoice" the Status Reason still shows "New". Interesting, although it shows new in the status reason, it now displays the option to select "Invoice Paid"

What am I missing?

Thanks to anyone who might have seen this.