Hello @itsparty! It sounds like you might be using an old version of the Square Point of Sale app. I would make sure that you are using the most up to date version of the app on a supported device as well a supported operating system. 

Also the reader your using is pretty dated. I would recommend upgrading to our new Magstripe Reader! It's free and you can order it directly from your Square Dashboard. Once you're logged on head to the Account & Settings tab on the left side of your screen. Then you will see a sub section labeled card reader! 

If the problem persists please let me know!