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I am monitoring the Internet usage of my applications and I noticed that iBooks initializes a connection to 23.221.221.248:443 whenever I select some text and then copy it.

Does someone know why, or how can the actual contents of that connection be exposed?

  • That IP address belongs to akamai which hosts much of Apple's content and some of it's services. I don't have a solution on iOS, but if you have a computer or high end router, you might be able to set up a web proxy (e.g. charles proxy) to sniff the content of the message. – bmike Sep 23 '14 at 19:41
  • @bmike Alas, I tried and it's an SSL connection. The dummy certificate that Charles proxy uses to record SSL connections doesn't fool him and the connection fails – Fiat Lux Sep 23 '14 at 22:42
  • Bummer - orchestrating a man-in-the-middle attack will prove more challenging than sniffing port 80 :( – bmike Sep 23 '14 at 23:06

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