Four patents VirnetX said were infringed by Apple have been deemed invalid by the U.S. Patent and Trademark Office, something which could potentially be a major setback in an upcoming retrial.

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A federal judge has tossed out a February ruling requiring Apple to pay patent holding company VirnetX $625.5 million over secure communications patents used in FaceTime and iMessage, and has ordered two complete retrials.

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Intensifying its patent infringement case against Apple, VirnetX has asked a Texas court to order an injunction against FaceTime, iMessage, and a VPN feature, while simultaneously asking for greater damage payments on top of $625.6 million awarded earlier this year.

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After objecting to the closing arguments made by Caldwell, Cassady & Curry attorneys representing VirnetX, Apple has now filed a motion for mistrial in the case that awarded a $625 million verdict after just a week of testimony and deliberation.

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A federal jury on Wednesday found Apple guilty of willfully infringing on four VirnetX patents, awarding the non-practicing entity $625.6 million in damages and ongoing royalties from a previous court finding.

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Patent holding firm VirnetX argued in court on Monday that Apple should pay $532 million for allegedly infringing on intellectual property protecting secure communications, a sum nearly 45 percent higher than an initial damages award vacated last year.

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Patent holding company VirnetX's infamous $368 million win over Apple -- which most notably resulted in changes to FaceTime that riled consumers -- has been thrown out by the U.S. Court of Appeals for the Federal Circuit after review.

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As Apple gears up to defend itself against another lawsuit from patent holding firm VirnetX, the iPhone maker was dealt a blow late last week after the presiding judge issued a series of pre-trial rulings denying Apple's motion to preemptively invalidate some of VirnetX's patent claims and preventing the use of invalidity as a defense against others.

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Patent holding company VirnetX on Tuesday announced that it will attempt to add Apple's most recent slate of products -- including the iPhone 5s and iPad Air -- to an ongoing patent infringement action that accuses Apple of violating VirnetX's secure networking patents.

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Apple will not be changing the behavior of its VPN On Demand services for some iOS devices, despite having lost a $368 million judgment to VirnetX.

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Following a $368 million judgment against Apple in a patent infringement case, the iPhone maker will make changes to VPN behavior in iOS 6.1.

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