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Protecting against web application threats using SSL

If you value your privacy and use Wi-Fi hotspots or other public networks, there is no tool more indispensable than a virtual private network. Yes, technologies such as secure sockets layer (denoted by an "https" in a web address) will prevent information transmitted between a PC and a web or email server from being intercepted, but this protection has its limits.

For one, the vast majority of web pages and email services don't offer the option to encrypt your traffic - at all. If you use a pop client to check email from Comcast, Earthlink or just about any other ISP, you're out of luck. Same thing goes for every single query you ever type into Google, Yahoo, WebMD or just about anywhere else.

Plus, even when sites do offer SSL protection during login, the vast majority remain vulnerable to an attack known as sidejacking, which allows anyone connected to your network (think co-workers or the person sipping cappuccino next to you at the Wi-Fi cafe) to read your email or view your calendar entries. This is true even if you entered your password into an encrypted page.

The reality of this insecurity sunk in deep for journalists covering the Black Hat security conference last month, after learning that three rogue reporters used easy-to-use monitoring tools to sniff traffic that traversed the press room computer network. The hack, which was carried out on an ethernet-based network, revealed at least one reporter's password. Who knows how many tell-tale web searches, instant messages or email were also exposed? Were it not for the loose lips of one of the perpetrators, the attack probably would have gone undetected.

Which brings us back to virtual private networks, better known as VPNs. By enclosing net traffic into an encrypted tunnel and funneling it to a trusted server (say, a net-connected machine at home or one controlled by your company), VPNs prevent people monitoring a Wi-Fi hotspot or other local network from making heads or tails of your communications. All they see are encrypted packets. Best of all, this protection extends to every web search, instant message or email you initiate, regardless of the service being used.

Like many small and medium sized businesses, El Reg is too cheap to equip its grunts with any sort of VPN [Have you asked? -Ed], and that exposes one of the great unspoken paradoxes of web security in the 21st Century: One of the most essential protections out there also happens to be the one that's least viable for those who don't work at a bank or Fortune 500 company. This is just plain wrong. Surely, there has to be a better way to secure yourself while surfing public networks.

Enter OpenVPN, a free and extremely powerful open source package that runs on Windows, OS X, Linux and assorted versions of Unix. This reporter has been using it for almost a month now, and it has worked great. James Yonan, the author and maintainer of OpenVPN, has plans to add lots of new features, so there's good reason to think it's only going to get better.

But don't say we didn't warn you: Because OpenVPN interoperates with a server, one or more clients and one or more local area networks, setup can be baffling, especially if you've never installed a VPN before. Indeed, it took this reporter three days to get it working properly. But now that it's installed, it seems well worth the work. OpenVPN already saved our bacon at Black Hat, and who knows where else.

What follows is step-by-step instructions for setting up OpenVPN on two Windows XP machines (one acting as the trusted server and the other as a client surfing the public network). Our apologies to users of other operating systems. While the exact menus and keystrokes don't apply to you, many of the general guidelines may still be helpful.

Reducing the cost and complexity of web vulnerability management

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