The US Securities and Exchange Commission has charged former Apple general counsel Nancy Heinen of fraudulently backdating stock options.
The stock market regulator accused Heinen of helping to backdate options given to Apple's top officers, causing the company to under-report its expenses by almost $40m (£20m).
The watchdog filed similar charges against Apple's former chief financial officer, Fred Anderson, but simultaneously settled that case. Anderson will pay $3.5m (£1.75m) in penalties in response to SEC charges that he should have noticed Heinen's actions and corrected the company's financial statements, the regulator said.
Despite the charges against the two executives, the SEC said Apple itself was in the clear. It praised Apple for its "swift, extensive and extraordinary cooperation" in the investigation, including prompt self-reporting, an internal investigation, sharing the investigation results with the government and implementing new controls to prevent future fraud.
In a response to the SEC case, Anderson's lawyer, Jerome Roth, blamed the backdating on Apple chief executive Steve Jobs. Anderson had "cautioned" Jobs that backdated options had to be approved by the board of directors, and relied on Jobs' assurances that had happened, Roth said.
In one instance in February 2001, Apple granted 4.8m options to six executives including Heinen and Anderson. To avoid reporting an $18.9m (£9.5m) compensation charge, Heinen backdated the options to 17 January when the company share price was much lower, the SEC alleged.
The SEC alleged that she then told her staff to prepare false documents showing the board of directors had taken action on the stock option grants that day. Anderson colluded by failing to disclose her actions to Apple's auditors, or ensuring that Apple's financial statements were correct, the SEC said.
Later, in December 2001, the company granted 7.5m options to Jobs. Again, Heinen avoided a $20.3m (£10.2m) charge by drafting minutes for a fake board meeting she said happened on 19 October, the SEC claimed. That meeting had never occurred, it said.
Both Heinen and Anderson personally received millions of dollars in unreported compensation through the backdating, the SEC alleged.
Scores of corporations have been charged with similar actions, but the Apple case is particularly serious because Heinen and Anderson were specifically charged with ensuring that the company created accurate reports of executive compensation.
"Instead, they failed in their duty as gatekeepers and caused Apple to conceal millions of dollars in stock option expenses," said Marc Fagel, associate regional director of the SEC's San Francisco office.
In its lawsuit, the SEC is seeking a penalty payment and refund of profits from Heinen, as well as an order barring her from serving as an officer or director of any other public company.
A comment from Heinen was not available.