Hi there, we have some troubleshooting suggestions in our help documentation here: https://docs.woocommerce.com/document/woocommerce-square/#section-43 can you have a look at that and see if one of those steps helps? If that doesn’t help, can you enable debug logging? There’s some documentation on that here: https://docs.woocommerce.com/document/woocommerce-square/#section-5 – see Debug Mode. After that’s been enabled can you try a test order and then revisit the WooCommerce logs screen under WooCommerce -> Status -> Logs and find the Square log there and see what clues it provides.
We haven’t heard back from you in a while, so I’m going to mark this as resolved – if you have any further questions, you can start a new thread.