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I recently made a tool that lets you configure skype to use a proxy. It forces it. Skype will only use a proxy if it cannot connect to the outside world without it. I recommend getting a good socks proxy because it supports UDP. I dont recomend doing calls over a proxy. It also might take a while for your IP to get updated on skype. This is great because it can prevent people from booting you offline.
Link:
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What it looks like:
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If you have problems with anything, please tell me. Feedback is nice also. (be nice.

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