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Order Status Won't Update from "Label purchased"

I'm having an issue where orders I've fulfilled won't update their status on the orders page and subsequently the order details page as a result. 

 

Even though the item has been delivered (and it says so on the next page if I click on the order) the status here never updates from "Label purchased"

nandorg_0-1647120708398.png

 

Did I miss a setting somewhere that needed to be configured? 

 

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