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This might be a stupid question, but are those postmarks made by the post office or are they stamped on by CCBill with their Pitney Bowes machine? If so, is it possible that they were stamped one day but not actually mailed until later?
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It's the PB meter machine stamp. It's also against postal regulations to "pre-stamp" first class mail like that and they will not accept it if you do (It makes them look bad... ie..delayed delivery...hahah)... thus why we have seen the double stamps before from Ccbill. This means they attempted to drop too late and had to rerun the letters back through (no additional postage) with the next day's date.
I believe that this time it was the post office's fault.