Q: How many times can a collection agency come after you for the same debit? If paid off?
A: If you paid a debt to zero, the debt is paid. You should probably take every bit of paper (letters, statements, etc., that you have on this debt) to a lawyer and let him or her determine if the debt was in fact, paid off.
A: Ideally, once. You should have an attorney review your situation so that you are certain what you are dealing with. I have seen many cases where someone did in fact owe multiple dents of a similar amount. I have also seen many cases where a debt collector illegally attempted to collect on the same debt multiple times.
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