A US district court in Texas has found Microsoft guilty of wilful infringement of two patents belonging to software maker VirnetX.
Microsoft has been ordered to pay $106m to VirnetX, which accused Microsoft in February 2007 of infringing the two patents relating to communications security.
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According to court documents, Microsoft faced treble damages because the infringement was found to be wilful.
VirnetX, which claims to have built its patent portfolio from a US Central Intelligence Agency security project, expects Microsoft to appeal the decision, according to US reports.
The VirnetX victory comes less than a week after Microsoft lost an appeal in its dispute with i4i over XML support in Office 2003/2007.
The US Court of Appeals for the Federal Circuit upheld the lower court's decision in August 2009 that Microsoft willfully infringed i4i's patent.
Microsoft was forced to issue a 12.3Mbyte patch for Office 2007 to comply with a US court order banning the use of custom tagging after 10 January 2010.