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Will a card with a chip still work on a square card reader if I swipe it?

I currently run a golf outing, and only have the card reader and the outing is on Friday September 23rd. I rather not purchase the chip reader at this time if I do not need to, since I only use the reader one day a year. 

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Yes it will work as long as it has the magnetic strip on the back of the card. However, you are assuming more liability risk, if you swipe instead of dip a chip card.

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We are a non-profit who sells Christmas trees every year.  We do not have access to internet or Wi-Fi at our point of sale.  We do not have a cell phone that we can dedicate to the Square card reader.  If we purchase the Square Terminal, how does it connect to Square to process the transaction?

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