Tracking information is triggered to TrackShip after you add tracking and fulfill the orders (change the order status to Shipped).
TrackShip will not automatically track orders that are already in Shipped status before you connected your store, or if you get a connection issue status or insufficient tracking balance.
You can trigger orders that are already fulfilled to be tracked by TrackShip from the dashboard by clicking on the Get Shipment Status icon, or from the WooCommerce orders admin, you can check all these orders that you want to trigger and from the bulk actions menu, choose the Get Shipment Status option and apply.
.