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in my machine I have two Windows OSs plus a Linux based one and I have Skype in them all. I don't mind Linux because there software is already different, but I wanted to sync my profile between both Windows so that I have access to all the conversiations and settings independently of which I'm using.

So I created a directory junction of %AppData%\Skype\username but when I change OS when I start Skype I get a message telling me that the password was wrong and I have to input it again. This works until I change to the other where I get the same message.

Is it possible to share Skype's profile across OSs? If so, how?

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I don't know if it is possible without having to have to enter the password again, they probably used a different format to store information in Windows XP and Windows 7. You could try symlinking %AppData%\Skype\username\chatsync instead, since there is where the logs seem to be but I don't have a XP around to try that out. – Xandy Nov 8 '12 at 11:32

If Skype is running simultaneously on multiple machines - it should sync automatically.

If you want Skype history to be available in every OS, you should manually copy chat history from one OS to another. This is described in the article below >>

How do I transfer my Skype chat history from one computer to another?

If you have existing dropbox account - you can go further and make Skype history and settings be stored in Dropbox folder, then make this folder available in every OS you need.

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