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What generation is your Square terminal? I still have a v1 and was disappointed to learn that it doesn't support Bitcoin payments. (I too was able to activate it, but not use it).
https://squareup.com/help/us/en/article/8384-identify-your-square-hardware
GENESIS
No upgrade in the immediate future. I don't have the budget for a new register (usually $799, currently on sale for $599). I'll reevaluate if there's customer demand.