Have you ever wondered where your Skype chatlogs are saved so that Skype can show you a chatlog on your mobile of a chat you had done with your computer, and reportedly even if you have saving chatlogs disabled on your computer? I found that issue for the first time like a year ago, and more or less suspected that Skype stores our chats on their servers. But this seems not to be the case at last (it would be a pretty bad breach of privacy anyway.)

It turns out that chatlogs are only stored on the users’ devices and only for their own chats of course, but they can be pulled from a second device of your own or the device of your chat partner when loading the history. This is a direct P2P transfer and therefore, nothing is saved on Skype servers. This pulling seems only to happen with mobile devices (like the Skype client on Android) and seems to be impossible with desktop clients, which save the history either right away or not at all when chatlogs are disabled. From a professional standpoint, there is of course a certain security risk involved in this “pulling” option in that it allows to restore chatlogs from the computer of a chatpartner (without the partner being aware!) to get unauthorized access to chat logs that have either been deleted from a computer or not saved there at all. A bit of a strange feature after all.

Source: Skype community thread “Delete history from server?” p.2

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