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An English businessman, who thought he had permanently erased the conversations from his iPhone, is suing Apple when his wife found messages he had sent to sex workers on the family iMac. The man, who wants to be unidentified, had been in contact with prostitutes over iMessage. He believed that the messages that implicated him had been removed from his iPhone.

Nevertheless, the messages were still viewable on the family’s iMac because of the synchronization of devices connected by the same Apple ID. His wife filed for divorce as a result of this discovery. In his 5 million pound lawsuit, the businessman accuses Apple of neglecting to warn customers that removing a message from one connected device does not erase it from all other devices that are linked to it.

The man suffered serious personal consequences after learning of the communications. The act of divorcing his wife has cost him in excess of five million pounds. He called the event “painful and raw,” implying that if the letters hadn’t been found so harshly, a more reasonable conversation would have preserved his marriage. According to the man’s attorney, Simon Walton, Apple did not explain to customers how to delete messages.

He said he would like to speak with other Apple users who have encountered same problems in an attempt to make this a class-action case. The businessman maintains that this could have been avoided if Apple had communicated more clearly.

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