We have had the exact same issue for a couple years without resolution. When our printer doesn't respond and I don't see it in the Square settings, I unplug the cable from the bottom of the Square Stand and wait a couple seconds and then plug it back in. That seems to "wake up" the printer about 60% of the time. Sometimes you have to repeat that process a few times for it to work, and unfortunately, we have to do this every 3 or 4 transactions. We also noticed that the issues are worse when we plug in our chip reader to the hub. The issue appears to be communication between the square stand and the hub itself. We have replaced the iPad, the stand, the hub, and the printer... the issues never went away, so after 2 years of frustration, we are currently looking at other options for replacing our POS system with another provider. Everything about the Square system has been fine except these constant hardware issues that, looking at these forums, appear to be VERY common.

All that being said, I think Square is fine for the very small business that has low customer volume and can deal with the frustrations that inevitably come with their rampant hardware issues. The software systems are great (with the exception of the lack of the ability to have the customer's name automatically printed on their receipts without having to manually add it as a note), so if you can deal with the rest of the frustrations it's not a terrible option. But now, with more providers out there, and some with significantly lower transaction rates, we feel like it's a good time to shop around.