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But what I understand the least is, in every one of these cases where they've obviously lost and are still on the line for whatever debt they were hoping to get canceled, they act as if they've won; complete with laughing-so-hard-I'm-crying emojis.

Crazy is crazy, but a letter saying literally, "we have no contract with you," and "your debts are solely your's" is being read as a win? Or are they just laughing because they think they wasted 8 months of some public servant's life?