Tracking info and misdelivered, then forwarded mail

I had one very important and expensive piece of mail sent out to my old mailing address 7 days after I had set up mail forwarding. I've called the Post Office twice now asking about having the mail retrieved and forwarding it to my new address. In the case that they do forward my mail, would the associated tracking number update and show that the mail is once again in transit? It still shows as [ Delivered, In/At Mailbox ].