Sometimes, you may run into issues with your Square Stand whether thats from things like firmware updates or iOS updates. For example, we've seen instances in the past where the KioskBuddy Beta app would crash when plugged into a Square Stand. Typically restarting the Square Stand helps with these kinds of issues.
To do this, open up the Square POS app, then navigate to Settings > Hardware > Stand > then push the Restart Stand button. Here's a screenshot of that screen (see upper right button to reset):