In 2012, Apple was sued by a patent holder, VirnetX, for violating their patents with FaceTime and iMessage. In particular, VirnetX owns 4 patents that describe a particular process for secure, highly available communications, which they claim several of Apple's products use without permission. Apple first lost this suit in 2012, then vowing to fight the ruling, which would cost them $368 million. After redesigning the software and another court loss, the result is $626 million in penalty.
To add insult to injury, VirnetX is asking for additional relief in the form of an additional $190 million, and a permanent injunction blocking Apple from providing these features until such a time that the two companies can reach a licensing agreement on the patents. Assumable, the redesign of the software did not get it far enough away from the patents to protect Apple from additional penalties or suit.
Apple is asking, in exchange, for a new trial, claiming among other things that the lawyers for VirnetX misrepresented the evidence, and even the false information did not support the infringement claim. They claim that the company is going for a broad injunction in hopes of finagling a larger licensing fee; essentially extortion.
The judge has not yet ruled on the additional requests, but said he would "get orders out as quickly as possible."