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I wanted to add a comment to this thread but I couldn’t as it is marked as resolved.
https://wordpress.org/support/topic/woocommerce-square-disconnects-every-month/
We have this same issue of occasional disconnection from our site to Square account. We always need to check in and re-connect again and we are losing potential orders until we do so.
We are using version 2.1.5 and I believe this version has the fix for that that is described in the thread.
Are there any other causes that trigger this auto disconnection issue?