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I think Square could have tried to be more understanding of this use case.

He did clearly explain that the linked account didn't keep a balance and that he was willing to pay the negative balance in his Square account with other sources.

I don't see this as shockingly poor customer service, but Square should have just disabled the automatic debiting on his account as he was a long time trust worthy customer.

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Trustworthy? Jason already demonstrated he is not trustworthy, since he failed to keep the necessary amount of funds in his linked account to cover any chargebacks that may occur. He screwed up, and he expected Square to pay for it.

Square was out the funds immediately. Jason could have avoided fees by funding his account the same day, or by simply keeping some reasonable amount in the account for potential chargebacks.

Square should not be required to keep a person on call to handle special cases like this or to ask merchants nicely for funds for every chargeback to an unfunded Square account. Automated ECH transfer from a linked account is fair and efficient, and once it is initiated can't be stopped.

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