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Been trying to find an answer to no avail. Probably I just don't understand the terminology... So if anyone may shed some light in plain English, that would be awesome.

I connect to a paid VPN through the OpenVPN protocol and at work, I connect through the company proxy, so I have set up the VPN to use the company proxy. That works fine.

How secure is such a connection? Does the company proxy know where I connect to and can the proxy know what websites I surf to?

OpenVPN is the only protocol the proxy allows me to use. PPTP is somehow blocked.

Thanks for your answers.

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OpenVPN is a 'SSL VPN'.

Therefore, the IP address your VPN client connects to is known to the company proxy. The traffic within the tunnel should not be visible to the proxy.

OpenVPN's long-running SSL connections are also a giveaway.

However, if you are using a Windows workstation provided by the company, chances are that it has anti-virus and other monitoring software on it and there is a good chance that admins can know what you are up to because your browser history and the network requests to the local workstation's networking subsystems are still loggable.

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  • ok, thanks a lot. any idea how to make prevent the local workstation's networking subsystem to not be loggable. so, if i have dns set to google's dns, use the privacy mode in my browser and connect through openvpn to an anonymous vpn, I can still be monitored by my company. seems to me that pretty much makes anonymous vpn providers unusable...?
    – David K.
    Feb 25, 2013 at 10:22
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    All I can say that tracking of network requests is doable if you have monitoring software installed on your workstation. If there is no monitoring of the workstation, then the proxy will only know of long-running SSL connections to a specific external IP address and host name.
    – Akber Choudhry
    Feb 25, 2013 at 10:25

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