PORT ORANGE, Fla. - WFTV dug up more information about Port Orange's troubled finance department.
Water billings errors cost the city at least $1 million.
Now, new emails show the city didn't collect more than $200,000 from a billboard and a towing company.
In an email, the vice president of Clear Channel Outdoor said the city has not cashed a rental check for land the company pays to rent from the city since 2010.
The uncashed checks add up to $57,000.
In another case, WFTV found A&A Wrecker owes the city $146,000, but the city did not notice the 29 missing payments.
"In those cases there weren't billings that would signal the finance department. We need to receive these funds back. We're going to address that," said Port Orange spokesman Kent Donahue.
A civil investigation of the water billing problems found city finance director John Shelley appears to have "failed to provide proper oversight."
Government watchdog Ted Noftall found out that Shelly has also been working in the CPA firm he and his wife own.
"I fail to understand how the chief financial officer of any organization would have time to conduct a business on the side," said Noftall.
WFTV called John Shelley's CPA firm to find out how many hours he's been putting in, but they would not comment.
A frustrated email sent by the city's comptroller reveals more problems may soon surface.
She writes, "I currently have 570 emails which have not been reviewed … cannot physically do any more."
Shelley is using vacation and sick time until his retirement date next month.