It happens more often than you think. Plus, odd issues, like a glitch with their servers causes the card reader to not work. Theres a ton of device verification and security checks on those readers that bounce back and forth between their servers. Square having a bad day? Everything works, but your reader wont sync, wont read cards = you're done for the day.
Days like this aren't the "norm", but constant aggravating issues are pretty much a weekly thing.
It got so bad, we just got an old-school merchant account with a reliable card reader. ZERO issues almost with that, ever. It's a little funkier, but the merchant account is 1/4 the cost to run than Square. Not as fancy of a webui from the merchant provider, but eh, all the same connections to Quickbooks for the accountants.