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I use my own VPS to serve as a PPTP gateway for my personal PC/laptop/android. It uses 128bit encryption, and MS-CHAPv2 for authentication.

The questions are: is it enough to secure my connection against unwanted snooping in public/company/school WiFi? How my password complexity affects the security of the encryption? And finally, is there a way to check if my packets are being encrypted?

I assume the potential attacker is only casually interested in my packets, and not out there to get me. Also, I understand that OpenVPN would be the most secure solution, but it's relatively more complex to set up, and has more configuration point of failures for someone as inexperienced as I am.

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In Aug '12 Microsoft recommended not to use MS-CHAPv2 technet.microsoft.com/en-us/security/advisory/2743314 – Dean Mar 3 '14 at 4:44
up vote 1 down vote accepted

A properly keyed 128-bit encryption PPTP is far beyond the realm of casual snooping. Your password is certainly the weak point of the system.

The best thing you can do for a password is to randomly pick letters and numbers and then memorize it rather than to choose a word and then substitute letters from it (auhwJSNw12 is a much better password than Aw3s0me).

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