Hii Popericky,
Technology is great when it works but, a challenge to figure things out when something goes wrong. Assuming you have Square's Reader for Contactless & Chip - have you tried to reset the unit - there's list troubleshooting steps here. If you have exhausted all of the options listed on that page, there may be something wrong with reader that can't be fixed however, as a last resort, a call to Tech Support be needed.
jk
