How Secure is VPN over unencrypted wifi networks?

By madflyguy ·
I've tried googling similar arguments several times, and all I ever find are people's opinions and speculation. I want to know if someone has objectively tried cracking passwords and other sensitive data being sent via vpn over an unencrypted wifi network. I personally am not savvy enough to do this - I can capture packets but wouldn't know where to begin decrypting passwords, etc...

If you know of a site that has done this, or have personally done such work, let me know or please point me in the right direction. Thank you.

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All Answers

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Security will never be totally black or white.

Security is a matter of degrees and layers. The more appropriately applied layers, the more secure the network is. I also look at security requirements for each individual situation using a RoI business perspective. Meaning I always try to have the value of protected product be substantially less than the cost required to obtain the protected product.

George Ou has a good article about this very subject and for what it's worth I agree with its tenets.

The article states the importance of using multiple layers of security and best practices. Which in most circumstances will make VPNs over secured/encrypted Wi-Fi links an acceptable risk. I also think that actual documentation as to processes will not be helpful as pen tests are situationally specific.

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VPN over wifi

by SYNner In reply to How Secure is VPN over un ...

as long as you have a tunnel from your workstation to a VPN server, then the traffic inside the tunnel is secure even over wifi.

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by nvious22 In reply to VPN over wifi

Try Ethereal and Cain&Able. These are pretty good sniffing and cracking tools.

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