But I don't really know why I had to do that - in plenty of other places I can charge ~$5 without signing. And the software was controlled by Square. So effectively, Square Wallet helped me solve a problem that Square caused in the first place.
Now I have Google Wallet enabled for tap payments on my phone. Every time I use it I feel like I'm living in the future. Except I can only use it in Duane Reade.