Basic button clicking tool

We have a system that we use to place orders with our customers. When it works correctly, the purchase gets downloaded to our ordering system, then the ordering system calls out to the drop shipper and places the order. But if something goes wrong, for example: the item is not available or has any kind of error, the order fails and sits until you click "retry" to try and reprocess the order. The retry button is right next to the order, it's a physical button you click. The issue is we have so many orders that enough fail to where we are clicking retry for hours a day. I need a simple program made that, when it sees the retry button appear, it clicks it. All the orders are one one page. So it does not need to do anything fancy. The order includes the date, so it should only keep retrying for one day. Afterwards, it should stop trying so we can place the order manually. Finally, we have about 10 instances. They are all the same program, just different user names and passwords as each instant runs a different store. Idealy we would like to run it on one VM. And have a simple ui that lets us add new instances and update the user name and password in case it changes. We know this is not a hard job, we just need someone to do it fast, as its getting annoying to keep clicking retry. I attached a screenshot of the ordering page. As you can see it's pretty simple