Hey @seedslocker,
Thanks for reaching out about this. I took a look at the information on our end and everything looks good with the connection to our servers and the transaction.
The label generation process is a little different than it was before. With WooCommerce Shipping & Tax, the print box popped up automatically after the purchase. In the new WooCommerce Shipping extension, you should see a confirmation message after the purchase, which has a “Print shipping label” button you can click to see the print pop-up.
Based on the info you shared, clearing the cache was a good approach. After doing that and reloading the order page, if the order status is still “Processing” and the tracking number shows in the “Shipment Tracking” sidebar widget, you can manually update the order to “Completed” and the customer will be notified and given the tracking number in that email.
Regarding the grayed out Refresh button, are you referring to the “Refresh purchase status” button (seen in this example: https://d.pr/i/u4RrF6)? Or something else?