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I share your frustration.
But I have a hypothesis. I would bet that the average Square merchant does not upgrade their app very often. They have to go to Apple's App Store and manually update.
I haven't seen the stats, but I bet most merchants simply don't have the latest version of the software.
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Square said at first that they "enabled bitcoin payments" and it ended up being a lie. Then they said "we enabled bitcoin payments for real this time, enabled by default, it just was not on by default last time" that ends up being false also.
I've been to MANY businesses that take Square, NONE OF THEM accept bitcoin, nor can it even be found anywhere in the menu on how to enable.
Every time I see a business with a square terminal I ask about paying in bitcoin and they have no clue what I'm talking about and there is no option to pay in bitcoin. Square is either poorly managed or they are just false advertising. Square is actually making bitcoin look bad by having people annoy business owners on paying in bitcoin then nobody being able to figure it out. It makes bitcoin look like a hassle when it actually isn't.
In the past week I've just given up on Square. Square is not the great thing I thought it was going to be for bitcoin adoption.