Apple is notorious for its ability to win key courtroom decisions but the Cupertino-based company has just come on the receiving end of a hefty fine following an East Texas jury’s decision that orders it to pay $368.2 million in damages to patent holding company VirnetX.

The decision, revealed by Bloomberg on Twitter, comes in response to VirnetX’s claim that Apple had infringed on a range of its patents which, it claims, are used in a number of its services, including FaceTime.

VirnetX was originally said to be looking for at least $900 million from the tech giant, 9to5mac reports, and, though the fine levied is some way smaller, it is certainly a sizeable amount that will grab attention in the tech community – even if it has been dished out on U.S. election night.

VirnetX has history when it comes to winning large patent cases against big firms. Back in May 2010, Microsoft was forced to pay up $200 million for infringing two patents, specifically a virtual private network technology used in Microsoft’s Windows and Office communication server products.

It doesn’t stop there since VirnetX currently has cases ongoing against Cisco and Avaya. It has struck licensing agreements with a range of firms in the past, including NEC and phone systems-maker Mitel.

This summer Apple won a key U.S. patent case against bitter rival Samsung, which saw jury hand down a fine of more than $1 billion to the Korea company.

A hearing scheduled for next month will see if that case will result in any of Samsung’s infringing devices from being banned from sale in the U.S. Any such measures will be significant blows for the world’s top smartphone maker.

Image via Flickr / Andrew