Two former executives at America Online face criminal charges after an FBI investigation into claims of fraudulent transactions with a software supplier.
AOL has agreed to cooperate with the US government's investigation
The duo - Kent Wakeford and John Tuli - have been charged with conspiracy, securities fraud, wire fraud and making false statements.
Prosecutors claim the pair colluded with executives at PurchasePro to inflate revenues at the two firms.
Time Warner, AOL's owner, is paying $510m to settle related civil charges.
It said last month that it had reached separate settlements with the US Department of Justice and the Securities and Exchange Commission.
The allegations relate to deals done between AOL and small software provider PurchasePro before the former's merger with Time Warner in 2000.
It is alleged that executives from the two firms conspired to artificially boost revenues and to meet sales targets by reaching secret sales agreements which were not disclosed to auditors and investors.
Mr Wakeford and Mr Tuli -and four executives from PurchasePro - Charles Johnson, Christopher Benyo, Joseph Kennedy and Scott Wiegand - have been accused of forging contracts and making false acccounting entries.
They also face charges of destroying documents and making false statements to investigators.
Between them, Mr Wakeford and Mr Tuli -who worked in AOL's Business Unit and NetBusiness Unit respectively - face four counts of securities fraud, four counts of making false statements and 22 counts of wire fraud.
If found guilty of all charges, the two face prison sentences of at least 50 years and heavy fines.
"The investing public must have accurate information to make sound decisions," United States Attorney Paul McNulty said in the indictment, laid down in the Eastern District of Virginia.
"These defendants swindled the investing public. This indictment charges them with lying to their investors about the true revenue of their company."
AOL has agreed to cooperate with the Department of Justice's investigation in return for it deferring charges that the company aided and abetted securities fraud in relation to the transactions.
Six former executives of PurchasePro, a Nevada company which has since gone bankrupt, have pleaded guilty in connection with the investigation.