Apple on Tuesday was ordered to pay $502.6 million to VirnetX Holding Corp. after a grand jury in Texas found that the iPhone maker infringed patents related to secure communications, according to Bloomberg. The judgment is the latest in an 8-year-old legal battle between Apple and VirnetX, a company that makes most of its money from licensing patented technology that creates virtual private networks over the internet. VirnetX filed a trio of lawsuits in 2010 alleging that Apple's FaceTime, VPN on Demand and iMessage features infringed four VirnetX patents. A verdict in February 2016 ordered Apple to pay VirnetX $625.6 million in damages after two lawsuits were combined. But in August of that year, a federal judge voided the verdict, saying that combining two lawsuits into a single trial confused the jurors and was unfair to Apple. He ruled that both cases needed to be tried separately.