Microsoft has filed lawsuits with eight resellers it accuses of illegally importing software into North America.
The lawsuit, which reaches around the globe, sees dealers from the US, Canada, Egypt and the Netherlands Implicated.
Microsoft is claiming that those named in the lawsuit illegally deceived their customers by falsifying details and supplying them with software that didn't have the necessary licenses.
The software at the centre of the case is its Student Media application suite, however, there are also allegations that certain companies sold customers illegal Certificate of Authenticity labels.
It has also take action against the distributors, which it alleged supplied the software.
"Microsoft has alleged that HW Trading BV and its principal, Samir Abdalla, received more than $3.7 million (£1.79 million) from just three dealers in the US between March 2006 and May 2007 in payment, in whole or in part, for unlicensed software," Microsoft said in a statement.
"These substantial profits were possible only because HW Trading and Abdalla did not purchase and transfer the necessary licenses for the software and, as a result, paid only pennies on the dollar for the software media."